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Best Men’s Watches

Watches are one of the few pieces of jewelry that any man can wear that is universally acceptable. Other jewelry like rings, earrings, necklaces and bracelets will have their detractors (myself included).

So for that reason alone, a watch is an accessory that every man should have. From a practical perspective, they are also nice for telling the date and time. But obviously not as required now that we’re carrying smartphones around with us all day long.

Just like I discussed in the series intro, there’s something amazing about owning a finely crafted piece of history and engineering perfection.

Whether you’re a watch guy or not, I think any self-respecting man should own a watch or two.

Before I get into the exact watches you should own, let me first answer the most common questions I get from clients, readers and viewers about watches:

What type of watch to wear with what outfits?

Suit = Dress Watch – you should never, ever wear a diving/chronograph/sport watch or anything but a leather or other hide strap with a suit. It drives me crazy when I see metal bracelets or nato straps with suits because they’re so casual in nature and they take away from the formality of a suit. It’s a SUPER amateur move.

Business Casual or casual outfits – Dress watch or Sport watch with a metal bracelet, leather/nato/rubber band. You can also wear a dress watch with them, but it depends on how “polished” your casual outfit is. If you’re in shorts and flip flops, that might not look right with a dress watch.

How to Match a Watch To Your Outfit

It’s pretty simple. If you’re wearing:

  • A suit with black dress shoes and belt.
    You should be wearing a dress watch with a black leather strap.
  • A Suit with Brown dress shoes and belt.
    You should be wearing a dress watch with a brown leather strap.
  • Anything outside of a suit, even if you’re wearing dress shoes, you can wear any type of watch you’d like – that includes dress watches as well as any sport, chrono, diver, pilot, etc. type of watches.

What size should your watch be?

If you have a smaller wrist, around 6″, then go with a 40mm or smaller.

If you have average to a wider wrist, around 7″ or bigger, then go with a 40 to 44mm sized watch.

Most older watches, including Rolex’s diving watches, were 38mm or less, but they’ve since shifted to 40mm to follow the trend of larger watches now.

Traditionally, dress watches were made to be smaller and fit under your shirt cuffs, while diving or chronograph watches are bigger so they’re easer to read while doing the activities they were designed for.

It’s really up to your personal preference. I’m a little new school in that I think dress watches don’t need to be tiny – my favorite IWC dress watch (below) is very large for a dress watch, but I still love it. Unless your wrists are extremely small, then any size between 36 and 44mm will be fine. Which is fortunate because almost all watches fall within these sizes anyways. It’s when you get into vintage watches that the sizes tend to be smaller. So if you prefer a smaller watch, then vintage may be right for you.

How Many Watches Should You Own?

To cover all your bases, you should own 2 to 3 watches. You can absolutely get away with owning only one (which I’ll discuss shortly), but 2 or 3 different types of watches will cover you for all the outfits and scenarios you’ll encounter. A lot of my clients who are into watches own usually double or triple that amount, but we’re talking about the barest of essentials right now and anything else would be a speciality or just not used as much.

What Watches Should You Own?

1. Silver Dress Watch with a Black Leather Strap

Here’s the basics of what this watch should be. If you own one watch, this should be it. That way it’ll cover you for the most scenarios. You’ll also need a brown leather band to swap out as your outfit accessories dictate according to the matching rules I discussed earlier. So scroll to the bottom to check out my favorite band/strap site to get your extra straps.

Your black leather strapped watch should have the following features:

Silver Case

You want a silver case because, just like with the hardware on your belts, it’ll match with everything. If you were to get a watch with a gold or black case and black leather band, it won’t match as well or be too sporty to complement the rest of your essential wardrobe items.

As for the size of the case, that’ll depend on your preference and what looks best on you, but a classic dress watch is supposed to be very thin and small (sub 40MM, usually), but I’m a little new school in this regard and don’t mind a taller or larger case, something like the 44mm IWC cases is fine, but right on the edge, for me. Honestly, go smaller if you have a small wrist, and bigger, if you have a wider wrist.

White Dial

The dial of your watch should be white because it’ll match perfectly with everything you could possibly throw at it. Black, blue, skeleton or other dials won’t match as well or will come off as too sporty or gaudy. I just think of all the sleezy salesman guys wearing their Movado watches at the bar after work – bleh.

Black Leather Strap

You can also use a leather alternative or other hide – kangaroo, ostrich, alligator, etc. The one thing you should never do is wear a nato or rubber strap with a suit. If I can be blunt – it looks like shit and is an amateur move. The quickest way to look like a teenager or style blogger is to wear a nato or rubber strap with every outfit. Those should be reserved for casual outfits only.

In regard to the stitching on the strap, I’ll forever dislike contrasting stitching, just like I do on wallets, so ideally, the stitching should match the color of the strap.

Subdials or complications

I’m a little new school in that I don’t believe a dress watch needs to have the cleanest dial possible. I don’t mind a few subdials or complications like a power reserve, subdial seconds, moon phase or month/day date. Just don’t go crazy and use a chronograph with a leather strap as a dress watch, please.

2. Silver or Gold Dress watch with a brown leather strap

The requirements for your brown leather-strapped dress watch are nearly identical to the black leather strapped dress watch above – with one major exception:

This is the one time when a gold case is acceptable because the dominant color of the accessories you’d be matching with would be brown, regardless of the hardware color of your belt. I’d still prefer a silver case if given the choice, but a gold case would work just as well.

If you have the budget for only one watch, or only want to own one dress watch, then make sure to get a brown band to swap out with your silver cased watch as your outfit accessories dictate. It’s a little bit of a pain, but not so much that this isn’t an option. Changing watch straps is quite easy and I have a great place to get really nice straps for cheap.

The Best Dress Watches

IWC Portugieser and Patek Philippe

$12,000 – IWC Portugieser Automatic
$20,000 – Patek Philippe Calatrava White Dial

 

A lot of these watches come with black or brown straps.

$30.00 – Timex Easy Reader Date
$65.00 – Stuhrling Original Ascot II
$65.00 – Bergmann Date 1933
$90.00 – Bulova Classic Dress Watch
$200 – Bulova Dress Watch
$220 – Tissot T-Classic Tradition
$230 – Mondaine Swiss Railways Evo 
$260 – Graf Zeppelin Hindenburg
$300 – Orient 2nd Generation Bambino
$500 – Rossling & Co Bogart
$520 – Junkers Bauhaus
$530 – Hamilton Intra-Matic Silver Dial
$650 – Tissot Heritage Visodate Automatic
$650 – Frederique Constant Classics Index Automatic
$1,100 – Junghans Max Bill Chronoschope
$1,600 – Tag Heuer Carrera Calibre 5 Automatic
$1,800 – Junghans Max Bill Automatic
$2,500 – Cartier Tank Solo  
$2,500 – Montblanc Heritage Chronométrie Automatic
$2,780 – Nomos Tangente 38 Datum
$3,500 – Breitling Transocean Chronograph 38
$3,600 – Omega De Ville Prestige Co-Axial 39.5 MM
$3,700 – Nomos Minimatik
$6,000 – Cartier Ballon Bleu de Cartier
$7,600 – IWC Portugieser Chronograph
$12,200 – Jaeger Le-Coultre Reverso Classic Large Duo Face
$15,000 – Omega De Ville Trésor Omega Master Co-Axial 40 MM

3. A Chronograph or Diving Watch

These watches are often called Sport watches, as well. You want this type of watch to round out your collection because it goes with any outfit from business casual on down. Unless you’re wearing a very sharp casual outfit, you shouldn’t be wearing a dress watch. That’s when a sport watch comes in to play. And please, for the love of all that is holy, please don’t wear your sport watch with a suit. I immediately know a guy doesn’t know much about looking good when I see a sport watch with a suit.

Here’s the details of what I look for in a good sport watch.

Black or Blue Dial

If I had my choice, I would choose a black or blue dial, with a slight edge to blue, as long as it’s more navy like Omega’s Speedmaster in Titanium (below) and not a royal blue like the Rolex Submariner in 16k white gold. The latter is just way too loud.

Silver Metal Bracelet

There’s nothing better for casual outfits than a diving or chronograph watch with a metal bracelet – in either titanium or stainless steel. Just like in the dress watches above, I prefer these materials and colors over a black or gold bracelet because it goes with everything and all the hardware on your belts, tie bars, etc. I also really love to see the metal bracelets swapped out for leather, rubber, perlon or nato straps, as well, but metal bracelets are a necessity for any sport watch – so you want to make sure it comes with that, first. For different watch straps, scroll down to the bottom of this article for my favorite place to get additional straps.

The Best Sport Watches

omega-rolex-ashley-weston

$11,000 – Omega Speedmaster – Moonwatch Omega Co-Axial Chronograph 44.25 MM
A quick note about the Speedster – the blue is much, much darker in person. The official images do it no justice.
$8,000 – Rolex Oyster Perpetual Submariner Date

$75.00 – Casio Super Illuminator Diver
$80.00 – Stuhlring Aquadiver
$100 – Parnis p101506 Mechanical
$125 – Fanmis Submariner
$150 – $200 – Seiko 5 Sports Automatic (also in a dark blue version)
$400 – Orient Mako USA II (has blue & black options)
$500 – Steinhart Ocean 1 Black
$450 – Tissot V8 Quartz Chronograph
$450 – Borealis Bull Shark
$550 – Seiko Prospex Kinetic Dive Watch
$660 – Certina C024.447.11.081.00
$700 – Hamilton Seaview Day Date Quartz Blue Dial (Also make blue dial & automatic versions)
$700 – Victorinix Maverick Stainless Steel Bracelet Watch
$800 – Longines Hydro Conquest
$910 – Christopher Ward C60 Trident Pro 600
$1,000 – Hamilton Jazzmaster Seaview Chrono Quartz 
$2,000 – Tag Heuer Aquaracer Calibre 5
$4,000 – Tudor Pelagos
$6,000 – Omega Seamaster 300 Omega Master Co-Axial 
$6,000 – Omega Speedmaster Moonwatch Omega Co-Axial Chronography
$7,850 – IWC Aquatimer Chronograph
$15,000 – Rolex Daytona

The Best Watch Straps and Bands

First and foremost, there’s no substitute for OEM straps or bands. But a really close second is my favorite aftermarket strap/band site – CheapestNatoStraps.com. Don’t let the name fool you, they’re neither cheap, in terms of quality, and they make a lot more than nato straps.  I’ve been swapping out watch straps and bands for clients for a long time now and this is the only place I go for aftermarket straps.

I talked to the owner, Sofie, and she was kind enough to offer you an additional 10% off your purchase if you use offer code: AshleyWeston

Special Thanks

A big thanks to reader/viewer Travis and the team over at www.Horobox.com for letting me bounce thoughts and ideas off them and providing their expertise and insight for this story. Definitely check them out!

Accessory Essentials Pocket Squares Wordpress Headers

Pocket Squares

Pocket squares are an essential accessory because when I talk about the smaller details that set the average guy apart from the well-dressed gentleman, this is exactly the type of accessory I’m referring to. It’s an easily forgotten item that adds a little extra polish to an outfit and really sets you apart from the average guy.

If you’re relatively new to pocket squares, the worst thing you can do is go overboard with them. I see it all the time. It’s a very fine line between looking sharp and tacky. Classy and subtle wins out over loud and flamboyant every time. So please don’t complicate your pocket squares any more than necessary.

Before we get into the pocket squares you should own, let me answer some of the common questions I get asked about pocket squares.

When to wear pocket squares

Anytime you’re wearing a jacket, either with a full suit or a blazer or sport coat. You can also wear them with unlined/unstructured blazers like I discussed in my Summer Essentials ebook. But, never, and I mean never, should you wear a pocket square with an overcoat or top coat.

Do I always need to wear one with all my suits and blazers?

No, but I’d suggest wearing one more often than not. To me, the more casual the outfit, the less necessary one becomes. But even then, the quickest way to add a little extra polish to an outfit is with a pocket square.

How Do I Match My Pocket Square to my outfit?

First off – if you’re matching your pocket square to your tie exactly – stop immediately.

It’s a rookie mistake I see a lot of guys making and it looks bad 100% of the time. I just think of all those silk tie and pocket square sets in prom photosshudder.

Matching your pocket square to your outfit is pretty straight forward.

The safest thing you can do, which looks great 100% of the time, is to match your pocket square to your shirt. You will NEVER go wrong there – as long as you’re not wearing some obnoxious dress shirt color like red or orange. Even then, it wouldn’t look… horrible. So do that if you’re going tie-less or wearing a black tie.

Solid tie that isn’t black

Make sure your pocket square is a similar color (not exact) to the color of your tie. Or, if you’re using a white pocket square with colored tipping, make sure the tipping is a similar shade of the same color.

Patterned tie

Find a color in the tie and have your pocket square, either the tipping, pattern, or solid color of your pocket square have a similar color in it. It doesn’t need to match perfectly, but it should have a similar shade of the color as your tie. So if you’re wearing a blue tie, have a blue shade in your pocket square.

Plain tie

Match your pocket square to your dress shirt. It doesn’t need to be perfectly matching, just a similar shade of the same color. That will keep a nice contrast between the items you’re wearing.

Going Tie-less

Again, match your pocket square to your shirt color.

So if you’re wearing a blue suit and white dress shirt, then you can wear a white pocket square.

What Material Should My Pocket Squares Be?

This one is simple: cotton.

Cotton works in 100% of situations, no matter the outfit, color, etc. and goes perfectly with your essential silk ties. So don’t waste your time or complicate things further by even considering other materials.

I occasionally use wool or linen pockets squares with clients or on shoots, but they have very specific use cases and cotton pocket squares would still work in all of these situations, so stick with cotton and you’ll be just fine. For silk pocket squares, I think I can count on one hand how many times I’ve used them over the course of my career.

What Colors and Patterns Should My Pocket Square be?

I’ll always default to classic and timeless colors and patterns so stick with these and they’ll go with any suit or jacket you’ll own:

  • Plain white (if you have 1 color, this is the color)
  • White with gray or navy tipping
  • Navy or gray gingham patterns

Any other types of patterns or colors and you’re venturing into territory that’s outside the scope of this series and where things can go wrong very quickly if you don’t know what you’re doing – and trust me, most guys don’t know what they’re doing in this department, even the so-called “experts”.

I’ll do a whole other video or series about patterns and materials later on, but that’s next level stuff and is not appropriate for the Essential Accessories Series since these are the items that need to work with my Men’s Wardrobe Essentials and also need to work for every guy, regardless of his age or body type.

How to fold a pocket square

Check out my article and video about the 3 best ways to fold a pocket square.

Best Pocket Squares

Honestly, it’s hard to go wrong with any pocket squares, as long as they’re cotton and you’ve stuck to plain white, white with colored tipping and navy or gray gingham patterns. So if you have a preferred place to get your pocket squares go ahead and use them.

I get hit up by a gazillion tie and pocket square companies all day long, but for all my pocket square needs – and they’re not paying me to say this – I use TheTieBar.com.

I’ve been a customer of theirs since they were a little company, who didn’t know who I was or what I did for a living and and they’ve continued to impress me each and every time I order from them. Suffice it to say, they’re amazing. And trust me, I use them A LOT.

The Tie Bar Solid White Cotton Pocket Square
The Tie Bar Solid Pocket Square with Midnight Navy Border
The Tie Bar Solid Pocket Square with Dark Charcoal Border
The Tie Bar Novel Gingham Navy Pocket Square
The Tie Bar Metric Plaid Charcoal Pocket Square

Pocket Squares Outfit Inspiration

The king of all pocket square inspiration photos is my friend Rainier over at TheDressedChest.com, my images below pale in comparison to his, so go check him out, as well.

Ties Mens Accessory Essentials Wordpress Ashley Weston2

The Best Men’s Ties

Just like all the other essential accessory pieces, you want your ties to work perfectly with all the items in your essential wardrobe. If you own a suit or blazer, then you absolutely need ties! Unfortunately, I see a lot of guys also completely crapping the bed with their ties.

A lot of men are wearing ties that are:

  • too wide or skinny, which completely throws off their proportions
  • tied with the wrong knots
  • not matching their outfits
  • really odd textured or patterned ties
  • the wrong material or fabric weights for the outfit

A big mistake most men make, whether they’re just starting out or have a little better handle on their personal style, is thinking they need to go overboard and have their accessories be these big statement pieces. That’s when men get into trouble.

Some men think it’s “boring” to stick to the basics, but they’re basics because they work for everybody and look timeless and sharp. And with the right accessories to round out your outfit, you’ll look well-dressed throughout your entire life. If you never own another type of tie in your life, my suggestions will cover you for every situation you’ll ever need.

How to Match Ties To An Outfit

The most common question I get about ties is how do you match them to and outfit. And it’s pretty simple:

The safest thing you can do, which looks great 100% of the time, is to have a similar color in your tie (not exact, just a similar shade) to any other color you’re wearing in your outfit – outside of your dress shirt.

So if you’re wearing a gray suit, white dress shirt and black dress shoes, wear a tie that has black or charcoal/gray in it. If you’re wearing a navy suit with brown dress shoes and charcoal socks, wear a blue or charcoal tie. If you’re wearing a gray blazer with dark wash jeans and brown boots, wear a tie that has some blue or charcoal in it. Brown leather jacket and boots, wear a tie with some brown in it.

That’s it.

Anything outside of that is next level stuff and can go wrong quickly if you’re not sure what you’re doing. You can go your entire life only following this rule and you’ll never go wrong – I promise.

What materials should your ties be?

You really only need ties in two materials to cover you for the whole year.

  1. Silk Ties
    Silk ties work year-round with every kind of outfit where a tie can be worn – dress, business and casual.
  2. Knitted/Woven Ties
    For the Spring and Summer months only – Check out Summer Essentials Ebook for details about those specific ties, but since they’re not for year-round wear, I won’t cover them in this article.

Any other types of materials, like pure wool or linen, have pretty small use cases and definitely won’t be as versatile as the above options and you should wait to get them until you’re much further on your style journey.

What color ties should you own?

Like all the items I recommend in the essential wardrobe series, you want to stick to black, charcoal, and navy, with one exception – which you can throw in there, if you like, and that’s silver or light gray.

These colors will go with 99% of the outfits you’ll wear. Just like with tie materials, any other colors will have specific use cases and are outside the scope of this series.

Once you’ve gotten those basic colors, then and only then can you start expanding to lighter shades or darker or brighter colors like burgundy, brown and other pastel or jewel tones. Again, that’s once you get more comfortable and really understand how to add them to an outfit.

But if choosing tie colors is still tough for you, then those default colors go with pretty much everything and you’ll never have to worry about not looking sharp and put together.

What patterns of ties should I own?

First, stick with plain, solid colored ties in the colors I discussed in the previous section. Then, you can move onto some striped ties with no more than 3 colors in them (ensuring at least the major color in the tie is one the colors I discussed above) and you can also throw in some smaller polka dotted ties in there, too. Also in the same colors I discussed previously.

What Size Tie Shoud You Own?

Follow these rules for your tie widths based on your height and body type so your proportions will always be balanced. Trust me, I deal with clients of all shapes and sizes all day long and these tie widths will work for you.

These sizes are to be used irregardless of the lapel width of your jacket.

Tie lengths really don’t come into play because most places you’ll go don’t make tall or short versions anyways and they’re not entirely necessary unless you’re ridiculously tall (over 6’5″) or short (under 4’10”).

To take your tie width measurements, just use the widest part of the tie near the bottom.

Under 5ft 8in and very thin

You need to get a 2″ width tie. If you’re not sure if you’re very thin, then you probably have an average build. Under no circumstance should you ever wear this width of tie unless you’re very thin and under 5’8” because it will look silly on you. I’d say that at least half the men I see wearing skinny ties shouldn’t be. Don’t fall into that group!

Under 5ft 8in & average/broad Build

Wear a tie that is 2.5″ wide.

5’8” to 6’3″ tall

thin to average Build

Wear a 2.5″ wide tie.

Large/Broad Build

You need a 3″ wide tie.

6’4″ tall and above (no matter your build)

You need a 3″ wide tie no matter what. This will help balance your proportions.

The Best Men’s Ties

I’ve been a customer and user of TheTieBar.com for years now, and they continually prove to me that they are, by far, the best place to get quality, affordable ties. I have never taken a dime from them to promote their products because they deserve all the praise and business in the world. Unless a designer has specifically made a tie for a client, I use them every time.

 

Black Ties (solid, striped, polka dotted)

The Tie Bar Black Grenafaux Tie
The Tie Bar Black Knit Tie
The Tie Bar Black Delta Stripe Tie
The Tie Bar Black Satin Dot Tie

Navy Ties (solid, striped, polka dotted)

The Tie Bar Navy Grenafaux Tie
The Tie Bar Navy Textured Solid Knit Tie
The Tie Bar Navy Trad Stripe
The Tie Bar Navy Satin Dot Tie

Charcoal/Gray Ties (solid, striped, polka dotted)

The Tie Bar Charcoal Grenafaux Tie
The Tie Bar Charcoal Knitted Tie
The Tie Bar Charcoal Pencil Pinstripes Tie
The Tie Bar Charcoal Shock Dots Tie

Silver (solid, striped, polka dotted)

The Tie Bar Silver Grenafaux Tie
The Tie Bar Silver Knitted Tie
The Tie Bar Silver Trainer Stripe Tie
The Tie Bar Silver Satin Dot Tie

 

Men’s Ties Outfit Inspiration

Best Mens Socks Ashley Weston Wordpress

The Best Men’s Socks

If you’ve downloaded any of my Free Ebooks, then you already know I’ve got some pretty strong opinions about socks – especially white ones. Most of my clients come to me with a drawer full of white, mid-calf length socks, possibly some ankle socks thrown in there, and a ratty pair or two of dress socks they pull out from time to time. This is unacceptable and frankly… gross. Before I took my nephew George under my wing, his sock drawer looked like this, but he had an excuse – he’s a little kid!

Socks area one of the few items in menswear when it’s perfectly acceptable to go absolutely crazy without looking ridiculous. You can use them to show off some of your personality and have fun with them. I’ve got clients who wear their favorite sports teams, crazy patterns, super heroes, etc. People will only really see them when you’re seated and they’re great conversation pieces, so I say go bonkers with them!

The Cardinal Sin of Socks

The only rule you cannot break from this day forward is: NO WHITE SOCKS – EVER. That’s it. They’re the cancer of the sock world. There’s no excuse or reason for owning any white socks anymore.

How many Socks Should I Own?

How many plain & patterned dress socks to have depends on what you wear and how often. I would say have enough to get you through a week, so about 7 pairs.

Best Material For Socks

Socks come in all sorts of fabrics/materials – wool, cotton, cashmere, silk, nylon or blends of each. In my experience, merino wool and cotton blends are best, because they’re more forgiving and comfortable than the other fabrics. They also look great and can be worn with both casual and dress outfits, and they’re just the right thickness. My choices at the bottom of this page will come in either fabric or one or the other. Silk, silk-blended or nylon-blended socks can only be worn with suits and dress shoes and will wear out quicker than other fabrics.

The types of socks to own

Plain & Patterned Dress Socks

Patterned Colored Dress Socks Mens AshleyWeston

I say dress socks, which are usually thinner than regular white socks, but I really just mean colored socks of any material. Think of these as your replacements for your white socks.

Like I said, it’s perfectly acceptable to go crazy here, but you should also at least have the standard colors of Black, Gray/Charcoal, and Navy in your sock drawer. That way, if you’re going to something where maybe it’s not appropriate – like a funeral or when it’s best to be more conservative.

As for material, like I said in the materials section, stick with merino wool or cotton blends because they’re most comfortable and can be worn with casual and dressy outfits. Just beware: Thick cotton or wool socks looks horrible with suits because they’re just too thick and informal. So if you need socks like that, wear them with casual outfits only.

Ankle Socks

DarnToughMensAnkleSocksAshleyWeston

These are to be worn when working out ONLY.

These are sometimes called low or short socks, depending on the company. Either way, they should have a little lip at the top. Anything higher, is to be avoided.

As for color, stick with black. White or other colors will get dirty and look gross very quickly.

For materials, merino wool or cotton blends are best.

No show socks

UniqloNoShowMensSocksAshleyWeston

These are appropriate for when you’re wearing shorts or cuffing your pants with any type of shoes – loafers, boat shoes, dress shoes, sneakers, etc.

You want to go with black because it’ll look the best the longest. You can also go with patterns and other colors, but no one will really see it, so it’s a bit of a waste. If you’re wearing white shoes, you can wear white ones, but they tend to get gross and nasty pretty quickly so I just avoid them. Whatever you do, don’t get nude-colored ones. It’s really gross looking.

How to match socks to an outfit

Patterned Or Colored Socks

(Any colors or patterns outside of the standard colors I listed above – black, charcoal & navy.)

The best thing to do, and what I do with my clients, is have a color in the socks, regardless of whether they’re plain or patterned, that is similar to a shade of any item in an outfit – whether it be your shoes, pants, shirts or accessories.

So if your tie or pocket square has a bit of blue in it, wear some socks with blue in them.

Just don’t match your socks to your shirt color if it’s white. Again – NO WHITE SOCKS!

Standard Plain Colored Socks

(Black, Charcoal & Navy)

Jeans and any color sneakers = any of the 3 standard colors.

Black suit (you better be wearing black shoes only!) = black socks

Navy suit (shoe color doesn’t matter) = navy or charcoal socks

Gray suit w/ black shoes = charcoal or black socks

Gray suit w/ brown shoes = charcoal socks

 

With that said, though, you shouldn’t worry about matching 99% of the time, though, because socks are one of the few places in menswear when you can (and should) go absolutely bananas.

When should you replace your socks?

When they’re worn thin in certain areas – usually around the heel or toes.

WornOutThinMensSocksAshleyWeston

When they’re faded, stretched out or stained.

WornOutFadedStainedMensSocksAshleyWeston

When they’re severely pilled (those weird little balls of fabric usually around worn areas are called pills). Pilling is usually the beginnings of them starting to get worn out in that area.

PilledMensSocksAshleyWeston

The Best Men’s Socks

Plain & Patterned Dress Socks

Darn Tough

DarnToughSocksMensAshleyWeston

They’re some of my client’s favorites – and mine, of course. They’re soft, super comfortable and about as durable as any socks I’ve encountered.

The kicker is that they come with a lifetime warranty, so if anything happens to them, send the company an email and they’ll replace them free of charge, for life. Obviously, this comes at a price, because they’re not cheap, but I don’t find the price too offensive compared to other brands that don’t offer a lifetime guarantee.

They’re a merino blend, so they wick sweat and moisture away from your feet, keep them cool in the summer and warm in the winter. They’re also seamless on the toes, so you’ll never have to deal with the discomfort of excess fabric around your toes.

Their cushion versions are the best, but even their non-cushioned socked are great. I found the other sizes, like their micro crew, to be too short and you’ll be flashing some shin when crossing your legs – which is to be avoided – so stick to the crew length or mid-calf lengths.

The only annoying thing is that they don’t sell socks directly, so you have to get them via third parties, like Amazon, REI or GearX

Uniqlo

UniqloMensCrewPatternPlainSocksAshleyWeston

If you want a great budget-friendly cotton options with LOTS of different colors and patterns, look no further than Uniqlo’s Crew Socks.

Kirkland & Gold Toe

These are good for plain/traditional colored socks. Unless you’re a member of Costco, you won’t be able to get the Kirkland Signature Cushioned socks.

Gold Toe’s are the old standby and are great for their price, but you’ll be replacing them once ever six to 12 months.

Ankle Socks

Just like with their dress socks, I really love Darn Tough Ankle Socks. They’re comfortable as hell and come with that amazing lifetime guarantee.

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For budget-friendly and variety, almost nowhere beats Uniqlo. They call their ankle socks “short” socks.

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No Show Socks

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I honestly say get the cheapest ones you can find because they’re all very similar. Some companies sell cotton blends and others sell more thin, nylon blended socks.

Some clients prefer one type over another, some like to have both and wear the thinner ones with dress shoes and the thicker ones with sneakers. This one is up to you, so try both and see what you prefer!

Again, Uniqlo reigns supreme! They call them “low cut” socks.

Dopp Travel Toiletry Kits Ashley Westion Wordpress Header

Dopp Kit or Toiletry Bag

If you ever travel, even if it’s just across town for the night, or to the gym, then you absolutely need a dopp kit or toiletry bag. No proper gentleman should ever be without one.

 

Why Own a dopp kit or Toiletry Bag?

The reasons you need one are many, but allow me to give a woman’s perspective and reasons for a moment.

In dating and life, we’re always looking at the smaller, subtle details to learn a little more about a person. We’re more sensitive to these subtleties and when a client asks why a dopp kit is important to own, I tell him that when a woman sees a man is organized and respects himself enough to have nice things, it makes us feel validated, like we found “a good one” because this small detail supports a notion that he probably has his life together and is a potentially good mate. It’s a very visceral, biological reaction that we get.

I often say it’s a similar thought to the old saying, “A messy bed equals a messy head” meaning that the way someone’s bed looks gives you some insight into their mental state.

On top of that, it’ll make traveling or going to the gym that much quicker and easier for you by keeping all your toiletries nice and organized. It’ll also help protect your clothing and luggage if you ever have any toiletries leak or spill.

What should a Dopp Kit do?

  • It should carry your toiletries, of course.
  • You also want it to be easy to use. There’s a lot of dopp kits out there, but my favorites are always the zip top style (see my choices below for examples) because the other styles aren’t as easy to pack or access items without having to move other things around. I had a client take a big chunk of out his finger with his razor while carelessly going through his non-top loading Dopp Kit and that’s what started me on the quest to find the perfect one. The next best alternative is the wide-mouth style (see the Shinola example below), but I find these tend to sacrifice some storage space to have the hinge. Even the original Dopp kit does this. My example below is the best I found with a hinge because it takes up less space than similar bags.
  • The last thing your Dopp Kit should do is last for the rest of your life. Unless things change dramatically over the course of your life, this should be the last one you ever buy. So if you’re hesitant because of pricing, don’t be. The cost per year will be so small that it’s absolutely worth it.

What Should it be made of?

Like with all the other bags I recommend in this series, I think there’s just no substitute for leather. It doesn’t stain as easily, and those stains will happen much quicker than your other items since it’s close to a lot of water and toothpaste, etc. Also, leather just looks much classier. Cloth or plastic alternatives are okay, but they just don’t compare, in my eyes.

What color should it be?

Just like all your other accessories, black or brown are my favorites. You can definitely go with other colors since not many people will see it, but I always stick to the classics here. Do you need to match it to your weekender bag? I would default to yes, because why not? But if you really like a brown dopp kitt and own a black weekender bag, then I don’t see an issue with that.

The Best Dopp Kits or Toiletry Bags

Jack Spade Mason Leather Dopp Kit

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Buy the Jack Spade Mason Leather Dopp Kit

It is my absolute favorite and one I’ve gifted to a lot of family and friends over the years. It’s simple, not too big or small, and has my favorite zip top design, so it’s very easy to access your items. I like just the simple pocket on the top, as well as the small side pockets for items that can fit there. Like all dopp kits should have, it of course has a waterproof lining, so if anything spills, it won’t be a total disaster for the items in your luggage.

I’d say that this one is perfect in every way.

 

Shinola Travel Kit

Shinola Dopp Travel Toiletries Kit Ashley Weston

Buy the Shinola Travel Kit

This is one of the few traditional style dopp kits that I could find with a hinge top opening, which allows you to access the entire compartment. Shinola’s leather is really damn good and even though it only comes in black, if you prefer this shape over the zip top style, this one is definitely for you.

 

This Is Ground Tech Dopp Kit

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Buy a This Is Ground Tech Dopp Kit

While these are not technically a toiletry bag or dopp kit, they call it their “Tech Dopp Kit”, I’ve found the multiple size opens and construction as close to perfect as possible. The only thing it’s missing is the waterproof lining, but as long as you’re relatively careful with packing your liquids, it wouldn’t call this a deal breaker.

I show the different sizes in the video at the top of this page, but I would recommend you get their “regular” size since it’s comparable to your average dopp kit’s size. But if you want something smaller or bigger, I think it’s great that they have those options available, too.

Definitely get it monogramed for that little extra special touch!

 

KILLSPENCER Dopp/Folio 2.0

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Buy the KILLSPENCER Dopp/Folio 2.0

Like all their products, it has a nice, supple leather with a great, tactical edge. I like it a lot because it has a unique look compared to all the other dopp kits out there and the inside is fully waterproof, so if anything spills, it won’t be a total disaster. While not a requirement, when you’re not using it as a dopp kit, it can also double as a folio by squishing it down a little bit. I thought this was a nice touch, but I don’t know how often it would be used like this. It’s definitely on the larger side of the spectrum, so if you’re looking for a larger dopp, this one is right for you.

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Sunglasses

So we’ve already established (in the series intro video) that the details in your wardrobe & appearance matter, and just like I talked about before, the first thing someone looks at is your face, so the things that sit ON your face, like sunglasses, should add to the overall sharpness of your outfit/appearance, not detract from it.

How many sunglasses should I own?

I’ve been asked this quite a few times and I think you should own 2-3 pairs. This will ensure your sunglasses will look appropriate with whatever outfit you’re wearing – no matter what. While you can use just 1 pair, I would recommend at least two to be safe.

Do I need to match sunglasses to my outfit?

You don’t technically need to match them to your outfit, but there’s an argument to be made for it, which I’ll get into in the next section.

What color sunglasses should I have?

In order to cover you for all outfits and seasons, you should own a black pair and tortoise shell pair. If you want crazier colors then you should definitely get them, but only AFTER you’ve got the basics covered.

Black

You want a black pair because they go very well with more formal outfits and/or they match with your black accessories – i.e. your shoes or watch strap. To me, it’s not ideal if you’re wearing brown accessories – shoes, watch strap, etc, and then throw on a pair of black sunglasses, but it is still perfectly acceptable because it’s far enough away from these other accessories that it won’t ruin the cohesion of the look. If you only have 1 pair of sunglasses, you should go with black because it goes with any outfit you could be wearing.

Brown/Tortoise shell

This color goes very well with casual outfits, but also looks fantastic with a navy suit and brown accessories. Again, you can get away with black sunglasses with a navy suit, but it’s not ideal.

Any Other Color

If you want to have a crazy fun pair, then go nuts here, but just don’t wear it with anything but casual outfits, otherwise you could start look like Bruce Vilanch. Again, a well-dressed man shouldn’t have anything standing out in an outfit, he needs everything to work in perfect harmony to create an amazing whole. This absolutely applies to sunglasses.

Aviators – The Exception

If your face shape allows you to wear Aviators and you want to wear those, always go with a silver/charcoal metal frame and black/grey/green lenses as the default or “black” option, like I talked about above. For your “brown” pair of sunglasses, go with a gold metal frame and brown lenses. You don’t want a black or brown frame because it looks cheesy and deviates too far away the timeless look of Aviators.


What Color Lenses should I have?

This one is simple and the default lenses are usually great, but here’s my preferences:

  1. Gradient – They look amazing and just give the sunglasses a nice, little extra touch of class.
    TomFordSnowdonSunglassesGradientLensesAshleyWeston
  2. Standard shaded/polarized – Most glasses will come with this type of lens that will probably match the color of the frame (black = black lenses, brown = brown lenses, etc.) and it’s perfectly acceptable, but if given the choice, I’d go with a gradient lens every time.
    Warby Parker Madison in Whiskey

Anything outside of these lens colors and types, included mirrored lenses, are a no go. They’ll detract from the polished look of your outfit and this is to be avoided because your accessories should never overshadow anything else you’re wearing.

Don't be like this guy.

Don’t be this guy.

The best sunglasses for your face shape

The type of sunglasses you should own is dependent on you face shape. You generally want the shape of your sunglasses to be the opposite of your face shape, so they’ll help provide balance to your facial features.

A quick note about the below chart, including other resources out there – most of them will be talking about as many as 10 different face shapes and trust me, it’s a waste of time. There’s really only 3 face shapes that every man falls into:

  1. Round
  2. Oval
  3. Square

Everything else is just nit-picking to fill up space on a website or magazine. The one that drives me the craziest is heart-shaped – that’s just an oval face with a wider forehead. If you’re considered heart-shaped according to the charts below, then just go with my oval suggestions.

You’ll notice that, outside of Aviators, I’m not recommending any frame-less style sunglasses and that’s because I think they just don’t look that great and never put my clients in them.

As for how to determine your face shape, the best resources I’ve found are from good ol’ LensCrafters and FramesDirect:

How To Find Your Face Shape Sunglasses Glasses Men Man Ashley Weston

How To Find Your Face Shape Sunglasses Glasses Men Man Ashley Weston1


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Round Face

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If you have a round shaped face, you want to avoid round frames and go for more square/rectangular frames (i.e. Wayfarer style) or teardrop frames like Aviators. These styles will help give your face some dimension and break up the roundness, which is a good thing!

A quick note about why I don’t recommend Ray-Ban’s classic Wayfarers: I hate the angle of the lenses on them. Yes, they’re classic, but that still doesn’t mean they’re good. Notice how the frames are resting on the cheeks in the below picture? It’s annoying as hell and just looks bad on everyone.

WayfarersSunglassesAngleAshleyWeston

Designer Options

Oliver Peoples Jack Huston Sun in Black + G15 Polar Glass
Oliver Peoples Jack Huston Sun in Cocobolo + Bourbon Polar Glass
Barton Perreira Hopper in Black 
Barton Perreira Hopper in Raven Tortoise Gradient
Gucci GG2269 in Grey and Brown
Saint Laurent Aviators in Gold

Budget-Friendly Options

Warby Parker Winston in Jet Black
Warby Parker Winston in Old Fashioned Fade
I love the classic, square shape of these sunglasses. For the price point, they don’t feel cheap or heavy.
J. Crew Irving in Black 
J. Crew Irving in Soft Tortoise
Aldo Draude in Silver
J. Crew Jack in Gold

 

Oval Face

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For this face shape, you’re lucky, because you have the most choices for sunglasses. You can wear round, square/rectangular, or rounded square-shaped sunglasses. The one thing you want to do is make sure the frames are as wide as your face – this is very important! Otherwise, it’ll look like you’re wearing kid sunglasses. Also, don’t you ever wear teardrop frames, like what most aviators have, because it’ll also make your face appear long or droopy.

Designer Options

Tom Ford Snowdon in Shiny Black
Fun Fact: Daniel Craig wore these in Spectre. If you have a round or oval face, these Tom Ford sunglasses are one of my all-time favorites! Everything about these square frames – the color, timeless design, and overall weight – couldn’t be better. Also, they’re the perfect width for oval faces which is very important because they’ll look disproportionate if they’re not as wide as your face.
Tom Ford Snowdon Sunglasses in Havana
Oliver Peoples Masek Sunglasses in Matte Black + Grey Mineral Glass
Oliver Peoples Masek Sunglasses in Cocobolo + Cosmik Tone Glass
Think of these Oliver Peoples sunglasses as the rounder version of the Tom Ford frames.
John Varvatos Grand in Black 
John Varvatos Grand in Tortoise

Budget-Friendly Options

AJ Morgan Round Sunglasses in Matte Black
Topman Tortoise Shell 50s Style
Warby Parker Downing in Jet Black 
Warby Parker Downing in Walnut Tortoise
The thinness of these plastic frames compliment its round shape and are great for men with oval or square faces. I also like that they kept the arms thin because some designers would go with wider arms which would make these frames look unbalanced. These aren’t as wide as the Tom Ford and Oliver Peoples frames that I recommend above, so if you do decide to try these out, then make sure they’re the proper width for your face.

Square Face

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For this face shape, you should look for round or teardrop frames. This will soften and balance your angular features. Avoid square or rectangle sunglasses because they’ll literally make you look like a block head

MinecraftBlockhead

Designer Options

Persol Sunglasses Suprema PO3007S in Black
Persol Sunglasses Suprema PO3007S In Tortoise
I love how sleek these frames are! The shiny finish and metal detailing on the arms adds to its sharp design. These are the perfect pair of sunglasses for men with square or oval faces.
Oliver Peoples Finley Esq. Sun in SMBK Moss Tortoise + Graphite
Oliver Peoples Finley Esq. Sun in Hickory Tortoise + Cosmik Tone Mineral Glass
Similar looking to the Persol sunglasses, the finish on both colors is matte and they’re slightly smaller in design.
Gucci GG2269 in Grey and Brown
Saint Laurent Aviators in Gold

Budget-Friendly Options

Warby Parker Percey in Charcoal Fade
I LOVE the black to grey coloring of these frames. They look so expensive for what you’re paying for and I appreciate the simple, thin design which softens (in a good way!) the sharper features of a square-faced man. And they’re incredibly lightweight.
Warby Parker Madison in Whiskey
Ray-Ban Aviator at Collection in Gunmetal
Ray-Ban Aviator at Collection in Gold
Ray-Ban aviators are a timeless, iconic design that’s perfect for this face shape because it helps break up your angular features with the teardrop design.

Sunglasses Outfit Inspiration

(LOTS of inspiration images are also in my Summer Essentials Ebook)

Best Mens Leather Briefcase Messenger Bag Ashley Weston

Men’s Leather Briefcases & Messenger bags

Okay, so the title is a bit click-baity. I’m sorry, but it’s time we got something straight. There is no scenario when you should be using a messenger bag – unless, of course, you’re a messenger. A messenger bag is the lazy/schlubby version of a briefcase with a removable shoulder strap. Messenger bags look horrible on their best day and any self-respecting man should avoid them. A modern briefcase is much more versatile and works in nearly all casual and dressy situations because of one simple thing: the removable shoulder strap. That little strap instantly turns a briefcase into a classy shoulder/messenger-type bag.

 

So if you’re hoping to see me talk about messenger bags and won’t consider using a briefcase with a shoulder strap instead, then:

ariGTFO

Your briefcase should:

  1. Look classy and timeless as hell – as always
  2. Be free of logos, contrast stitching, flourishes or patterns or needless shine – they’re tacky.
  3. Not be big enough for you to sleep in. – If you need that much stuff, it’s time to sit down and think about your choices in life, or go for a straight up utility item specifically built for this purpose. I’m thinking of those rolling briefcases that lawyers carry.
  4. Carry a 15” laptop easily plus a good amount of items/paperwork, etc.
  5. Have a removable shoulder strap and permanent handles.

Just like your weekender bag and leather backpack, the goal is to have something that shows you’re a man who cares about details and who values the items he chooses to carry with him.

What Material Should A Briefcase Be

In all my testing, the best looking and longest-lasting material is hands down leather. Any other material will stain or wear too easily. I’ve even tested some leather alternative briefcases and they just don’t compare.

What Color Should It Be

You want to stick with black or brown. I’ve looked into blues and gray briefcases and I can assure you that those colors will not age well, both from a style and durability perspective. So please, go conservative with your color choices here. You’ll thank me now and when you realize it’s been 10 years and you’re still carrying the same awesome briefcase.

You may have noticed in my weekender and backpack stories that I said to make sure they’re the same color because they will likely be carried together during trips. This rule can also apply to your briefcase if you’ll be using/carrying it more than a backpack.

When to use the shoulder strap

Just like I said in my backpack story – if you’re wearing a suit, blazer or sport coat, you should never use the shoulder strap. To do so will, at best, wrinkle the shoulder, possibly the lapel, and the back of your jacket. At worst, it’ll ruin the padding in the shoulder. If you’re wearing an unstructured jacket or more casual items, then that’s when to use the shoulder strap.

If you’re not using the shoulder strap, please take it off and keep it in the briefcase or at home.

The Best Leather Briefcases

Frank Clegg Zip Top Leather Briefcase

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Buy the Frank Clegg Zip Top Leather Briefcase

Just like his weekender bag, this is my hands-down favorite briefcase of the bunch. It’s the same, high-quality leather, awesome hardware and a basic but well-thought out design. LIke all his products, it comes with a lifetime guarantee against any defects.

One of the things I really love about this briefcase is the hidden shoulder strap hooks on the sides. So if you remove the  strap, no one would even know that it can be carried over your shoulder. I also love the side pockets on the front and back for slipping things in and out of quickly. It’s just a perfect briefcase in every way.

I have the double gusset version in my video, but the single gusset is also incredibly nice and roomy. I love that there’s options for sizing between single to triple gusset that you usually don’t find with most other brands.

If you pick up this briefcase, please also make sure to get it monogrammed. It just adds that little extra touch of class.

Coach Metropolitan Slim Brief

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Buy the Coach Metropolitan Slim Brief

For a more budget-friendly item, I really, really like this one by Coach. They always do a great job with their leather goods, but I have to say, they knocked it out of the park here. The leather feels great, the shoulder strap hooks aren’t hidden like with Frank Clegg’s bag, but they can be tucked into the front and back pockets to be a little more hidden, which is nice.

The interior pocket lining is very soft, almost like a microfiber. The side pockets are also lined with this material. It’s hard to not keep touching it. The shoulder strap could be all leather, but since it’s cheaper than the Frank Clegg briefcase, I’m fine with using some cloth in the strap.

Also, the logo is simply stamped into the leather, and it’s at the bottom of the bag, so major, major points for this. Normally, Coach (and a lot of other brands) would have it placed a little more prominently near the top, but I’m glad they chose the bottom, otherwise this briefcase might not have made the cut.

The one major knock I can give this briefcase is that it has metal feet on the bottom. If you saw my weekender story, then you know that they tend to get scuffed and pitted, which will scratch anything you set these feet on. But just like with the weekender bag, wrap some electrical tape around the feet and it shouldn’t be too much of an issue or be visible.

Over all, I was very impressed though.

Notes about the state of briefcases

So just like with leather backpacks, the pickings are extremely slim in this category, but these are honest-to-goodness the best picks out of the bunch. Everything else was either very cheap or tacky looking or ridiculously expensive for a reason that I couldn’t tell in my testing. Check the Honorable Mentions section below for details about the bags that just missed the cut in case these two don’t meet your requirements.

 

Honorable mentions

Shinola Slim Briefcase

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Buy Shinola’s Slim Briefcase

Love their leather and I like this one a lot, but it’s not as structured as I normally prefer a briefcase to be. So that’s why it wasn’t included.

Uri Minkoff Fulton Brief

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Buy Uri Minkoff’s Fulton Brief

It looks good for the price, but I thought the quality of the leather was a little iffy. I’d spend a little extra and get the Coach bag, if my budget allowed.

Mulberry Heathcliffe Briefcase

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Buy the Heathcliffe Briefcase or the Slim Heathcliffe

I’m a huge fan of Mulberry, but honestly, they’re about the same price as the Frank Clegg briefcase and I would go for the Frank Clegg 100% of the time.

Jack Spade Barrow Leather Slim Briefcase

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Buy Jack Spade’s Barrow Leather Slim Briefcase

I wasn’t the biggest fan of the floppy handles and that extra zipper on the bottom is pretty non-sensical.

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Men’s Leather Backpack

Like I mentioned in my article and video about weekender bags, a leather backpack is a necessity for every man because it’s the type of bag that fills a lot of gaps in your bag arsenal – like when you work in a more casual environment and a briefcase would be a little odd. Or when you need a bag for groceries, going to the coffee shop or you’re going on a trip and putting your laptop and other personal items in a weekender bag won’t fit or will be a little too rough on them.

You want your backpack to do a couple of things:

  1. It should look classy and have a timeless design.
  2. It should work with dressy and casual outfits (not with suits, though, more on that in a minute)
  3. Hold at least a 15” laptop
  4. Should be comfortable – of course.
  5. Should last you a long time

I think a lot of guys assume that a backpack is the one bag they need, no matter what they’re wearing and doing. This is mostly true, but with two massive exceptions.

  1. If you’re wearing a suit or blazers often, then a backpack should never be worn with any of these outfits because the shoulder straps will ruin the shoulder pads and wrinkle your jacket all over the back. Wearing suits or Blazers = carrying your bag by the handles and never anything else – which means you need a briefcase. Unless you’re going for the IT guy look, please don’t wear your backpack (or messenger bag!) with these outfits. Even a nice backpack, like the ones I’ll be highlighting, won’t look right with those types of outfits.
  2. If you’re needing a backpack for camping, lugging around your camera equipment or things like that, then you’ll need a specialty bag/backpack. You wouldn’t take a sedan off-roading, so please don’t do the same with your backpack. So if you have specialty items you need to carry around or are wearing suits or blazers often, then you need a bag specifically designed for those contexts – like a briefcase or camera bag.

What Material Should Your Backpack Be?

If you’re looking for something classy and functional, leather is the only option. Don’t get me wrong, I’ve seen some nice fabric or nylon ones, but they just don’t look right in as many scenarios as a leather backpack and they’ll wear or stain very easily.

Remember, you want your accessories to show you’re a man who cares about the details, and wearing a great outfit with anything but an equally classy backpack just looks like you missed the mark a bit. Think of those college kids you see with their Swiss army backpacks and sloppy suits running around conferences.

What Color Should You Get?

I like black, gray or cognac. But remember, as I said in my weekender bag story, this is the only time you need to match your accessory to another accessory – so whatever your weekender bag color is, your backpack should be a similar color. It doesn’t need to be perfectly matching, but black for black, brown for brown, etc. The reason for this is because your backpack will often be carried with your weekender on short trips, so you want some cohesion here.

I would honestly go for black because brown tends to show a little more scuffs and scratches, but if you really want to work a nice patina into a backpack, then there’s definitely no substitute for a brown backpack.

The Best Men’s Leather Backpacks

So let me tell you the state of the classy and timeless backpack industry or genre right now: It’s pretty awful out there. There’s so much crap out there. I’m not kidding when I say that just in the last year, I’ve tested at least 50 backpacks from every major and minor designer out there. There are so few brands that make a clean, nicely-designed and sharp looking backpack that won’t look silly or dated within a year or two. Aside from the ones I’ll show you, every other backpack missed the mark in some way or another.

This Is Ground – Venture Backpack

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Buy the Venture backpack

You might remember these guys from my wallets video/article and they’re back with hands down, the best leather backpack I’ve ever tested. The design is simple, classy and very well thought out. The Italian leather is really soft and supple with just enough stiffness to maintain the shape well. It’s just really nice to hold and use.

It has a lot of pockets and slots for all your items, including cables and chargers without feeling like it’s wasting space. It has two main compartments, one that is padded for your laptop and tablet or notebook, as well as some awesome pockets along the opposite side. Then the second big compartment is nice and wide open for whatever you want to put in there. I also really like this top zipper slot for your phone or wallet that is deceipity deep. My clients said they really liked this feature.

I know it sounds small, but their shoulder straps and back padding are the perfect width and very soft. I was worried that the thinner shoulder straps would dig in if there were some heavier items in the bag, but this isn’t the case.

A small point, but definitely a big deal for me, is where the shoulder straps are anchored to the bottom of the bag. See how they attach to the middle and bottom of the bag? This is awesome because it is supporting a good portion of the weight from the bottom of the bag, and not from the front side like most backpacks. I’ve definitely found other bags breaking, or the stitching coming loose at this exact point a few times, even after, what I’d consider, very light usage. While we’re talking about the straps, I love how they don’t have a bunch of extra slack on them. Even if you tighten or loosen them, you don’t have a bunch of excess strap flapping around. This is super annoying on a lot of other bags. Besides, your backpack should sit relatively high on your back, not on the lower part of your back or worst-of-all, your butt. I’m glad that This Is Ground knows this and doesn’t even give people the option!!

And if this bag wasn’t cool enough, it has a special, secret compartment in part of the bag for you to hide your valuables as well as the included Tile dongle, so in case you ever lose your bag, you can track it via the app.

I have it here in their cognac brown, which has such a nice, rich color and will just get better with age. But I also really like their charcoal black as well. Also, make sure to get the regular size, the mini size is small by a few inches and is much more geared for a woman.

KILLSPENCER – Special Ops Backpack 2.0

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Buy the KILLSPENCER Special Ops Backpack 2.0

If you want a backpack with a little more tactical edge to it, then the KILLSPENCER Special Ops Backpack is right up your alley. Just like with their weekender bag, their leather is really damn good. I especially love that they have it in this really nice Charcoal Gary color, which matches their weekender’s color perfectly. They also have it in black, which I also like a lot, they also make a nylon version, so it’s a great leather alternative bag, as well.

A note on the color in the image above – watch my video showing this backpack because that’s the actual, true life color. For some reason these images don’t represent the color correctly.

Like all their products, the design is well-thought out and classy and just like the Venture Backpack, their zippers are buttery smooth and the rest of the hardware is great.

The big pocket on the front is nice to have, but I’m not sure how safe it is if you’re utilizing it in a crowd. I know I’d be a little nervous keeping some valuables there.

The lining is also water and fireproof, so if you spill something inside (hopefully not), it won’t be such a disaster, for the bag at least. Another nice touch is the mesh interior pockets, which allow you to see what’s inside them. It sounds small, but trust me, it’s a very nice feature to have.


Matt & Nat – Dean Backpack

Matt_Nat_Dead_Leather_backpack_Ashley_Weston2

Buy the Dean backpack

If you’re looking for a leather alternative backpack, then I really like this one by Matt & Nat. Out of all the faux leather backpacks I’ve seen, this is definitely the best.

I really like the unique but not overbearing design and the hardware is surprisingly nice and smooth. It has a big top-loading storage area, with a laptop compartment and an extra pocket as well. It also has this outter pocket for some of your smaller items which is nice to have.

The only downside is that the woven straps feel a little cheap and I don’t know how durable this bag is in the longrun, but for a relatively cheap bag, this is perfectly acceptable.

I have it here in black, but I also like their brown color, which they call chili. So if you’re looking for a leather alternative backpack, this is the best I’ve seen – by far.


Honorable Mentions

Valextra V Line Backpack

VALEXTRA_Pebble-Grain Leather Backpack_Ashley Weston

Buy the Valextra V Line backpack

I liked it a lot, just like their wallets, but unfortunately it’s structure is too stiff and it looks like other designer bags that I just think look odd. It’s like wearing a box on your back, as opposed to something that’ll mold a little better to your body and it’s contents. It also just has one big compartment, with a pocket for a laptop and nothing else, which is a little annoying because then all your stuff will be banging around in it, or you’ll need some sort of organizer to then put into the backpack.

COTE & CIEL RHINE COATED CANVAS AND LEATHER

cote&ciel - RHINE COATED CANVAS AND LEATHER backpack Ashley Weston

Buy the Cote & Ciel Rhine backpack

It’s just a little too tactical looking for my taste. The front also looks like a little bit of a sad emoji. But for utility purposes, this bag is great! But it won’t fit a whole lot of stuff inside.

AER Fit Pack

Aer Fit Pack_backpack_Ashley_Weston

Buy the Aer Fit Pack

Even though it’s not leather, I really love this backpack because it’s so utilitarian. This is the perfect gym backpack, though, and even has an extra compartment for your shoes, which comes in handy a lot.

Mulberry Multitasker

Mulberry Multitasker leather backpack _Leather_backpack_Ashley_Weston

Buy the Mulberry Multitasker backpack

Love their leather products, including their weekender bag, and this one can be used as a shoulder bag and top handle bag, but it’s a little bit small in dimensions and just has a big pocket to put everything in. Organization isn’t so great with this one and it’s slight on the smaller side. While my top choices are 17” or more in height, this one is 15” which is right on the edge of looking like a girl’s backpack.

 

So that’s it. Those are honestly the best backpacks I could find – anywhere in the world. I’ve been working on this story for ages and I was shocked to discover these were the only ones good enough to recommend. Everything else was a weird size, didn’t have good storage, had a big ass logo on it, crazy contrasting stitching or just something was off about it. If you make leather backpacks and want to prove me wrong, then please contact me and prove me wrong!