7 Accessories You Should Get Rid Of Now

We’ve talked about how important it is to regularly clean out your wardrobe of items that are old, out of style, and no longer worth it. This goes for your accessories too. Accessories are a key part of your overall style, and a few wrong choices or out of date items can easily ruin an otherwise great look.

1. Wide bracelets

My position on this is well known, it’s time to ditch the stacked bracelets and wide leather straps. Their time has come and gone.

2. Too-wide ties

It’s important to keep an eye on your tie’s width. Not everyone should wear a skinny tie (it should be proportionate to your body type and suit style) but anything wider than 3” is just going to look out of date and out of style.

3. Belts with big buckles or large logos

Another item I’ve talked about before, get rid of ‘em! Belts should be minimal. The same goes for super-wide belt widths and contrasting stitching, definitely a big no.

4. Lapel flowers/pins

I don’t mind a bit of flair, like a thoughtfully chosen pocket square or tie bar, but at a certain point, less is more. You don’t need to add on a lapel pin/flower in addition to all the other accessories you’re wearing, it’s too much.

5. Extra-wide tie bars

If your tie bar goes past your tie, you’re in trouble. Additionally, anything more than 2 inches wide, (unless you’re a broader guy with a 44” chest or larger), is just too long.

6. Colored shoelaces

Another trend that had its day, simple and understated is the way to go with shoelaces. You want that nice pair of shoes to do the talking, not the brightly-colored laces.

7. Big, chunky metal rings

A simple band or signet ring is just fine, but large bulky rings just look dated and over the top.

How To Wear A Tie Bar

As I’ve talked about before, details like well-chosen accessories can make a huge impact on your outfit. Whether you call it a tie bar or tie clip, this classic accessory is an easy way to add a bit of extra flair to your dressy outfits.  But, there are a few easy tips you need to know when selecting and wearing one.

The two biggest, and really, only, mistakes you can make with a tie bar are: wearing it too high or low and using a tie bar that is not the proper size for your tie width. So let’s fix those problems once and for all.

 

Choosing The Right Size Tie Bar

The key here is to make sure your tie bar does not exceed the length of your tie width and hang over the edge, definitely not a good look.

For A Slim Tie

If you’re wearing a slimmer  2” – 2.5” wide tie, then you want to choose a 1” or 1.5” tie bar.

For A Standard Tie

If you’re wearing a standard 3” tie, then you want to use a 2” tie bar.

Now that you know how wide your tie bar should be, let me show you how to properly wear one with two different approaches.

How To Wear A Tie Bar

Now that you’ve got the right size tie bar selected, let’s move on to the right way to wear it. I highly recommend sticking to one of these two methods as any other way can throw off your entire look.

The OG Approach

This is the tried and true classic way to wear a tie bar. Your tie bar will be placed lower down on your tie which will prevent your tie from moving as much. It’s a more utilitarian use of your tie bar without it showing much. With your blazer on, attach your tie bar about 2 buttons lower than the breast pocket of your jacket.  There you go, the OG approach.

The Modern Approach

The modern approach is my personal favorite because it shows off the accessory a bit more and whether I’m styling for GQ or my clients for the red carpet, this is what I prefer do. To achieve this attach your tie bar slightly below your breast pocket – about 0.5”. Be careful though, any higher and it’ll look ridiculous.

No matter which way you choose to wear it, the right tie bar is an easy upgrade to your accessory game; try one out today!

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.

$65.00 – Stuhrling Original Ascot II
$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
$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
$3,600 – 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
$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!

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.

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

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

JackSpadeMasonLeatherDoppKitAshleyWeston

 

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

ThisIsGroundTechDoppTravelToiletriesKit Ashley Weston13

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

KillSpencerdoppfolio_34_black_1_12 Ashley Weston

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.

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

FrankCleggShoulderStrapHooks

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

CoachMetropolitanBriefcaseShoulderStrap

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

ShinolaSlimLeahterBriefcaseAshleyWeston

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

MulberryHeathcliffeLeatherBriefcaseAshleyWeston

Buy the Mulberry Single Document Holder Briefcase 

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

JackSpaceBarrowLeatherBriefcaseAshleyWeston

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.