Everyday Carry with George LaBoda

For this edition of our Everyday Carry series, Ashley sat down with George LaBoda to discuss his go-to EDC items and everything he relies on as a successful influencer and co-creator of Gents Lounge.

Thanks to George for joining us for this video and thanks to IWC, one of our favorite watch brands of all time, for helping make this video happen!

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POTW: The Best Men’s Polo Shirts Ever

I’m quite excited for my pick of the week because I’ve been constantly checking for the last few weeks to see if they’re available. Annnnnnnnd they are!! I’m sure you’ve already read my Essential Polo Shirt article so you know what to look for in a polo – so I present to you, my favorite polo shirt. 

H&M Polo Shirt - Ashley Weston

$10 – H&M Polo Shirt

Here’s a few reasons why I love them:

  • They have a great slim and stretchy fit.
  • The cotton fabric feels like a really soft t-shirt.
  • The collar has just the right amount of structure.
  • The price is very affordable. They’re currently on sale for $10.

Do yourself a favor and pick these up right now because they go in and out of stock constantly, and sometimes for weeks on end. The second I see them come up, I immediately order them because I’ve been burned in the past by waiting.

During this time of year, Dorian lives in these polos. He wears them all the time, but especially during the Spring and Summer months. I do want to point out, though, that the darker colored polos are not the most durable. I baby these by washing them in cold water with detergent, specifically for dark colors, and I let them air dry, but even still, the color for the darker polos will fade so you’ll need to replace them yearly if not sooner.

With all that said, these are still some of the best fitting and best looking polos ever.

Best Ways to Wear

I love polo shirts because they can easily be dressed up or down. If you’re running errands or want a super casual, yet put together look, then pair your polo with some dark wash jeans and white low top sneakers. Check out my Polo Shirt article for lots of other ways to wear a polo shirt, as well.

3-Outfits-Every-Guy-Should-Own-Ashley-Weston-1
$10 – H&M Polo Shirt Slim Fit in black
$168 – Diesel Buster 0607A
$75 – Adidas Originals Stan Smith 
$415 – Tom Ford ‘Snowdon’ Sunglasses
IWC Portugieser Automatic Watch

You can also throw on a black bomber jacket or navy Harrington jacket as well as some chukka boots or even casual dress shoes for a slightly more dressed up look that’s perfect for going to a party or heading to dinner/drinks.

$200 – Zara Leather Jacket
$250 – Fred Perry Harrington Jacket in black
$390 – Baracuta G9 Harrington Jacket in navy
$175 – Johnston & Murphy Conard Cap Toe Chukka in black

POTW: The Perfect Blue Chambray Shirt

I was doing a pull for a client when I randomly stumbled on this indigo blue chambray shirt and I had to share it with you. It’s not often that a simple shirt like this blows me away, but this one was something special. It was the perfect shade of indigo blue, the buttons where a similar color to the shirt, so they blended in nicely. And the fit was really darn good. If you don’t already have one (or a few) of these in your closet, get one – or many!

Chambray Shirt Ashley Weston$45 – Topman Navy Wash Twill Casual Shirt 

This shirt will definitely not be available for too long so be sure to order yours if you’ve been wanting a chambray shirt for awhile now because it’s so tough to find one this good.

Best Ways to Wear

Chambray shirts look great year round. You can wear it dressed up with a sportcoat, dress it down with a bomber jacket, or wear it on its own with the sleeves rolled up and paired with some chinos or grey or black jeans.

IMG_0682

$149 – H&M Wool Blazer
$45 – Topman Navy Wash Twill Casual Shirt 
$198 – J. Brand Tyler Taper Fit in Seriously Black
$75 – Adidas Stan Smith Sneakers

Bomber Jacket with Chambray Shirt - Ashley Weston

$250 – Life After Denim Flight Jacket
$45 – Topman Navy Wash Twill Casual Shirt
$75 – Adidas Stan Smith Sneakers

Chambray Shirt - Ashley Weston

$70 – Levi’s 511 Slim Fit Jeans (in black stretch, nightshine, or beluga grey)
$75 – Adidas Stan Smith Sneakers
IWC Portugieser Automatic Watch

16 Accessories Every Man Needs

These are, to me, the 16 accessories every guy needs to own, regardless of your age, occupation, and lifestyle. Some of these items you may not wear often, but there will be an occasion, as a grown man, when you will need them and you’ll be thankful that you thought far enough ahead to take care of them before it’s too late and you’re scrambling at the last minute. I’ve also included my favorites for each of these items below. But these points below are just skimming the surface compared to the much more through Men’s Essential Accessories Series I did recently.

Have questions? Curious what others think?

Join us in the comments section of the video above.

16. White Pocket Square

Like I’ve mentioned before, every man should have at least a grey suit. Even if you only wear it once every year, you’re going to need a suit. Along with that, looking well dressed is always about the details and a white pocket square is an easily overlooked item that really does make a big impact and it’ll only set you back a couple of bucks.

White Pocket Square Ashley Weston

$175 – Tom Ford Solid Classic Silk Pocket Square
$60 – Boss Solid Silk Pocket Square
$10 – The Tie Bar Solid White Cotton Pocket Square

15. Silver Tie Bar

This is another overlooked item. I talked about this in my article about the 12 Things Men Wear That Women Love, but a tie bar is something that adds that special touch to your outfit. It’s also so cheap to own so order it once and you’ll never think about it again.

Silver Tie Bar Ashley Weston$15 – The Tie Bar Silver Shot Tie Bar
$70 – J. Crew Sterling-Silver Tie Clip 

14. Solid Black and Navy Tie

These two ties will work for any suit you have in your closet, making them an absolute must have. Make sure the width of your tie complements your body type.

Black and Navy Tie Ashley Weston

$19 – The Tie Bar Grenafaux Tie (available in black and navy)
$60 – J. Crew American Wool Navy Tie
$60 – J. Crew American Wool Black Tie

13. Dress Socks

Get rid of your white socks. These socks can and should be worn as your everyday socks. If you need heavier duty, thicker socks for your job or because of the weather, there are plenty of companies that offer warmer versions.

Solid or Patterned Dress Socks Ashley Weston

$4 – Uniqlo Argyle Socks
$20 – Brooks Brothers Egyptian Cotton Jersey Knit Crew Socks
$15 – J. Crew Tipped Microstriped Socks

12. Sunglasses

Whether you’re a sunglass man or not, sunglasses are important because they’re going to protect your eyes from the sun, prevent you from squinting, which creates wrinkles around your eyes, and they can add a stylish, cool touch to your outfit. Check out my sunglasses story so you choose the right frames for your face shape.

Sunglasses 1 Ashley Weston 2

$415 – Tom Ford Snowdon Sunglasses
$98 – J. Crew Jack Sunglasses
$95 – Warby Parker Winston Sunglasses 

11. Baseball Hat

We all have those lazy days, myself included, where you just say F it, I’m gonna throw on a hat. When it comes to baseball hats I have very specific opinions about them so I shared some of my recommendations below.

Baseball Cap Ashley Weston

$48 – Gents ‘The Directors’ Baseball Cap
$22 – Flexfit Blank Snapback 2014

10. Black and Brown Oxford or Derby Shoes

Not only do these oxford dress shoes look great with your suit, but they also look nice with chinos, jeans, and trousers when you want to dress up a more casual outfit.

Black and Brown Shoes Ashley Weston

$395 – Allen Edmonds Carlyle Plain-Toe Oxfords
$750 – Prada Plain-Toe Bluchers
$175 – Johnston & Murphy Melton Cap Toe Oxfords

9. Black and Brown Dress Belts

Since you’re going to own dress shoes, you absolutely need to match your leather belt to your shoes.

Black and Brown Dress Belt Ashley Weston

$98 – Brooks Brothers Leather Dress Belt
$98 – Allen Edmonds Poplar Dress Belt
$25 – H&M Leather Belt

8. Weekender Bag

Everyone travels. Whether it’s to some exotic country, or across town, you’ll need to put your clothes in something AND trash bags are not an option. Like every accessory you own, it should not only serve it’s purpose, but look damn good at the same time. I have a whole article about weekender bags you should check out.

Weekender Bag Ashley Weston$965 – Frank Clegg Signature Travel Duffle (in black, chocolate or chesnut)
$800 – Killspencer Weekender 3.0 (in black leather or charcoal grey leather)
$115 – Everlane ‘The Dipped Weekender’ (in black/black, navy/black or reverse denim/black)

7. Dopp Kit

This item goes great with your weekender bag. Again, doesn’t matter if you’re traveling to another city or to the gym, a dopp kitt is essential because it’ll keep your grooming products organized and contained in a respectable manner.

Dopp Kit 1 Ashley Weston 2

$148 – Jack Spade Mason Leather Zipper Top Dopp
$300 – Shinola Travel Kit
$200 – This is Ground Tech Dopp Kit

6. Backpack or Briefcase with Detachable Strap

Depending on what you do for a living, if you live a more casual lifestyle or you’re a student, then a backpack is great. If you are in a more professional environment, a briefcase is best.

Backpack Briefcase Ashley Weston 1

Backpack

$800 – This is Ground Venture Regular Backpack
$210 – Cõte & Ciel Rhine Backpack
$120 – Aer Fit Pack Backpack 

Briefcase

$990 – Frank Clegg Zip-Top Briefcase
$895 – Shinola Slim Briefcase
$325 – Uri Minkoff Pebbled Leather Fulton Briefcase 

5. Casual or Dress Watch

Like the last point, which one you go with will depend on your lifestyle. Whether you’re a watch guy or not, any self-respecting man should own a watch or two.

Casual and Dress Watch Ashley Weston

Casual Watch

$7,000 – Rolex Submariner 114060
$3,400 – Omega Speedmaster Professional Moonwatch
$375 – Orient Diver Mako USA II

Dress Watch

$12,700 – IWC Schaffhausen Portugieser Automatic
$532 – Hamilton Intra-Matic Silver Dial Leather Watch
$195 – Tissot T-Classic Tradition Silver Dial

4. White Low Top Sneakers

Everyone has casual days, and white sneakers look so sharp on every guy regardless of your age or body type. If you’re really scared of wearing white, or think that it doesn’t look right, ease yourself into it with a nice low top lace-up black or navy sneaker.

White Sneakers 2 Ashley Weston

$370 – Acne Studios Adrian White Leather Sneakers
$75 – Adidas Stan Smith Sneakers
$65 – Converse Jack Purcell Classic Low Top

3. Boxer Briefs

All women find boxer briefs, specifically darker colors, so sexy on a man. And all men should be wearing them. Period.

Boxer Brief Ashley Weston

$26 – Exofficio Give-N-Go Boxer Brief
$13 – H&M 3-pack Boxer Shorts
$6 – Uniqlo Supima Cotton Boxer Briefs

2. Black and Brown Casual Leather Belts

Whenever you’re wearing jeans, chinos or shorts, throw on a casual leather belt because it’ll add a visually nice touch to your outfit.

Black and Brown Casual Belts Ashley Weston

$98 – Allen Edmonds Sun River Casual Belt
$295 – Salvatore Ferragamo Reversible Leather Belt 
$18 – H&M Leather Belt

1. A Quality Wallet

The things a man carries tells a lot about him and that’s no more true than with your wallet – check out my  article to the left for bifold, card cases, and phone wallet recommendations.

The below are only a few recommendations for bifold wallets.

Wallet Ashley Weston

$195 – Shinola Slim Bifold Leather Wallet 
$525 – Louis Vuitton Slender Wallet
$80 – Bellroy Low Down Wallet

Henley Shirts

Henley shirts are one of the few items that, to me, don’t really have a specific season they’re best worn in because there’s so many different versions for men. Other shirts, like T-Shirts, Polo Shirts and Dress Shirts don’t really have this problem since they’re pretty standard across the board no matter the season.

I love henleys, because they look sexy and masculine, especially when the top 1 or 2 buttons are undone to draw the eyes to your chest and shoulders to show off your physique in a flattering way. Hence, the image below.

BUT, and this is a big mistake I see a lot of men making – they’re not for every everyone. More on that shortly.

Let’s get into what to look for in your henleys based on the time of year.

Intro - Short Sleeve Sexy henley

Fabric

Generally, henleys will be made out of cotton, so there’s really not much choice outside of that, but you still need to consider fabric weights depending on the time of year. The main thing to know is that lighter weights should be worn in warmer months or in warmer climates and thicker, heavier fabrics in cooler months or climates. You can get them in everything from a lightweight summer weave, where it feels like a t-shirt, to thicker, quilted versions which will keep you warm during the cooler months.

You don’t have to worry too much when buying them because, based on the time of year, the brands will carry the appropriate weights. But I still want you to be aware of it just in case.

Henley Fabric Ashley Weston 2

Fit

Like all your clothing, including henleys, they should have a trim fit throughout the body and arms – no matter your body type. You never want it too loose anywhere because that’s when you’ll look sloppy and not put together. You shouldn’t be able to pinch more than 1-2 inches of fabric on one side of your stomach and no more than an inch around the bicep.

The image below highlights the proper fit around the torso and sleeves.

Fit - Perfect fitting henley shirt

I mentioned earlier that henleys aren’t for everyone, so let’s get into that right now since we’re talking about fit.

For Thin Gentleman

If you’re a thin guy, no matter your height, if you want to wear a henley, you absolutely need to nail the fit, especially if you’re going to wear a long sleeve version. If the fit is too loose, it’ll make you look thinner and more frail than you are – not good!

I only like long sleeve henleys on thinner men if they’re layered underneath a jacket, like the below right image. When worn on their own, it really spotlights and elongates your thinner torso, like image on the left. So if you’re a thinner guy and want to wear a henley on its own, then wear a short sleeve version since it’ll look similar to your t-shirts.

Henley Fit Ashley Weston

Bigger Gentleman

If you’re a rotund gentleman (aka you’re not in the greatest shape and have a belly), you cannot wear a henley shirt, period. Allow me to show you why and explain. See exhibit A:

Fit - Big Guy - Bad Example of henley

Because of the button placket on the front, coupled with the lack of a collar, a henley will shine a massive spotlight on your bigger neck and torso. This is when a polo shirt is perfect and should be used instead, because a polo shirt’s collar will visually keep your torso balanced and in proportion, so your top half doesn’t look so big compared to your bottom half. The image below of James Corden shows a guy with the exact same body type as the image above, but in a polo shirt. Talk about a night and day difference…

Fit - Big Guy - Good Example - Polo Shirt1

Best Ways To Wear A Henley Shirt

Think of your short sleeve henley as a t-shirt, they’re interchangeable in the same outfits, so that means they can be worn on their own or underneath a jacket.

How To Wear Henley - Short Sleeve

J. Crew Slim Broken-In Short Sleeve Henley
J. Brand Tyler Taper Fit in Rasalas
Allen Edmonds Hampton Ave Tan Leather Belt 
I would pair this look with white sneakers – Nike Tennis Classic Sneakers

For a long sleeve, you would normally wear these during the cooler months as a layering piece, so I styled Dorian in a long sleeve henley shirt underneath a bomber jacket, dark wash jeans, and sneakers.

Mens-Henley-Shirt-Long-Short-Ashley-Weston-2

Mens-Henley-Shirt-Long-Short-Ashley-Weston-3

Burberry Lightweight Lambskin Bomber Jacket 
J. Crew Wallace & Barnes Wool Henley Sweater
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Black Dress Belt  
Johnston & Murphy Conard Cap Toe Black Chukka

IWC Portugieser Automatic Watch
Ray Ban RB4258 Sunglasses 

During the warmer months you can wear them with the sleeves pushed up. As I mentioned in one of my other videos, women LOVE to see sleeves rolled/pushed up around your forearms.

How To Wear Henleys - Henley Sleeves Pushed Up On Forearms

My Favorite Henley Shirts

Here are some great short sleeve and long sleeve (lightweight and heavyweight) henley options that I love.

Short Sleeve Henleys

Short Sleeve Henley 1 Ashley Weston

$125 – Rag & Bone Classic Short-Sleeve Henley
$35 – J. Crew Slim Broken-In Short Sleeve Henley (White, Navy, Heather Grey, Black)

Long Sleeve Henleys

Rag & Bone Long Sleeve Henley Ashley Weston

$250 – Rag & Bone Giles Merino Wool-Blend Heavyweight Long Sleeve Henley Shirt
$40 – J. Crew Slim Broken-in Lightweight Long Sleeve Henley
$15 – H&M Jersey Lightweight Long Sleeve Henley 

Fall and Winter Boots For Men

There’s 3 types of Fall and Winter Boots for men that I love for this time of year – Dress, casual and chukka boots.

The reason I love boots for Fall/Winter is that they go so well with jeans, wool trousers and fall/winter suits. They also do a great job of keeping your feet warm and protected from the elements – while looking classy and more refined than a pair of hiking boots or something that’s just a straight utility item.

Now, if you live in an area with a good amount of snow or rain, then you should probably have specialty boots for the crazy days, too, but those are outside the scope of this article. 

The difference between dress and casual boots

Dress boots are more formal and can be worn with a suit or wool trousers. They have a sleeker profile, usually leather or dainite soles, and are made out of shinier calf skin, as opposed to cow hide. Dress boots are like dress shoes with a shaft, basically.

Casual boots usually have more room in the toe box, the leather is usually a thicker cowhide that is more matte, and the soles usually have lugs on them. They look a little less dressy and sophisticated, which is why they look so great with jeans, but you can also still wear them with wool trousers.

My Requirements for a good Fall/Winter Boot

These items apply to all the types of boots – dress, casual and chukka boots:

1. A slim profile and not chunky

Timberlands (right) are the exact opposite of what I’m looking for in a good boot. You want a nice, rounded toe box with a slim profile as well as sole like the image below.

dressvsworkbootashleywestoncropped

2. Plain, Cap Toe or Broguing

I like all 3 of them, but just like with my dress shoes, I’ll always prefer a plain or cap-toe, but broguing is also acceptable. Broguing is not really my preference because I think a lot of guys overdo it with the broguing, burnished toes, etc. Too much can easily look gaudy if you’ve got too much going on in your outfit.

plaincaptoebroguingashleyweston

3. Lugged, Dainite or Rubber soles

These will give great grip in any type of weather. A normal dress boot has smooth leather on the bottom and you will slip and slide like crazy in wet weather. If you’re not in a climate with rain/snow, then you can go with straight leather bottoms typically found on most dress boots, but I see no reason to do that when any rubber bottom aside from lugged will look very similar with the extra benefit of additional traction.

mensleatherbootsolesashleyweston

4. Be brown or black leather

Go with nice dark chocolate or walnut brown first, then get black if you don’t have them already. Brown is a great fall/winter color and is easier to wear with casual AND more formal outfits. But be careful about getting a really specific brown color, like oxblood. As I’ve said in my other shoe videos, it’s a great color but doesn’t compliment a lot of outfits, so get that color once you’ve got these basics down.

And please, whatever you do, don’t get those terrible boots that are already worn in. It’s much better for you to wear them in yourself and really personalize their look to your actual lifestyle.

5. NOT be Suede

For Fall and Winter boots, suede is the last material you should consider, unless you live in a dry climate like Southern California where it rains maybe 3 or 4 times a year. Otherwise, they’ll get screwed up very quickly with any amount of rain or snow. I don’t care how much scotch guard you use, nothing can stand up to that much abuse. So save the suede shoes for spring, please.

Can I wear boots with a suit?

Yes, but only when these 2 conditions are met:

  1. You’re wearing a heavier wool or tweed suit.
    For a visually heavy item like boots, you should understand fabric weights and pairing them with similar items. Even straight up dress boots can look odd with lighter weight wool suits. Make sure the wool is atlas 12oz thick. The easiest way to tell what a heavy wool suit feels like in person, is it should be as thick as a wool sweater (not as soft, though!)
  2. Your pants are hemmed to have no break.
    The hem of your pants will look sloppy and bunched at the ankle, otherwise. You can technically cuff the hem of your suit pants to do this, but if they’re super long, it’ll never look quite right. So I usually just get the pants hemmed to no break for this. But that means you can’t wear this suit with anything but boots now…unless you have your tailor let out the hem when the seasons change.

How To Tie Your Boots

Check out my shoe and boot tying video for how to tie your shoelaces properly.

Best Ways To Wear Boots For Men

fallwinteressentialsbootsashleywestonoutfit1

Topman Black Cotton Bomber Jacket 
TopMan Ribbed Turtle Neck Slim Fit
Rolex Oyster Perpetual Submariner Date
Tom Ford Black Snowdon Sunglasses
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt

fallwinteressentialsbootsashleywestonoutfit2

Parajumpers Anthracite Urban Genesee Jacket
Brooks Brothers Milano Fit Button-Down Collar Dress Shirt
Rolex Oyster Perpetual Submariner Date
Tom Ford Black Snowdon Sunglasses
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt

fallwinteressentialsbootsashleywestonoutfit3

Topman Faux Suede Flight Jacket (It’s technically a Peuterey jacket, but it’s only available in Europe)
Brooks Brothers Milano Fit Spread Collar Dress Shirt
IWC Portuguese Automatic Watch
Tom Ford Black Snowdon Sunglasses
H&M Black Melange Wool Suit Pants
Allen Edmonds Decatur Ave Dress Belt

The Best Fall Winter Boots For Men

Casual Boots

Budget Friendly

Aldo Acerrassi

$200 – Aldo Acerrassi

$175 – Aldo Etausen Boot (2 colors)
$175 – Johnston & Murphy Conard Wingtip Boot (3 colors)
$220 – Jack Erwin Carter Wingtip Boot (2 colors)

Designer

$350 – Allen Edmonds Long Branch Wingtip Boots


$318 – FRYE Tyler Lace Up (2 colors)
$395 – Wolverine 1000 Mile Boot 
$725 – Crockett & Jones Coniston Tan Boot
$775 – Crockett & Jones Islay Wingtip Boot

Dress Boots

Budget Friendly

Calvin Klein Darsey Brown Boot

$140 – Calvin Klein Darsey Dark Brown Leather Boots

$60 – Stafford Deacon Wingtip Leather Boots (2 Colors)
$135 – Stacy Adams Madison Boot (2 colors)
$140 – Calvin Klein Darsey Black Leather Boot

Designer

Allen Edmonds First Avenue Black Boot

$995 – Saint Laurent Polished Leather 

$645 – O’Keefe Algy Split-Toe Weatherproof Pebble-Grain Leather Boots
$748 – Brooks Brothers Peal & Co. Leather Wingtip Boots
$1,098 – Brooks Brothers Peal & Co. Cordovan Boots

Chukka Boots

Budget Friendly

Johnston & Murphy Fulton Chukka Black

$140 – Johnston & Murphy Fulton Black Chukka

$130 – Clark’s Desert Boot in Brown Suede
$75 – Aldo Granges Chukka Boot
$175 –Johnston & Murphy Conard Cap Toe Chukka (2 colors)
$198 – Johnston & Murphy Fulton Brown Chukka
$225 – Vince Camuto Branx Two-Eye Chukka (2 colors)

Designer

Allen Edmonds Dundee 2.0 Chocolate

 

$250 – Allen Edmonds Dundee 2.0 Suede Boots (2 colors)
$378 – FRYE Weston Chukka (3 colors)
$1,500 – John Lobb Elmer Chukka

 

That’s it! I hope you liked the article. Please share it via one of the buttons below if you did. 🙂

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!

Plain T-Shirts

A plain, short sleeved t-shirt is an essential because they’re super comfortable, timeless, and everyone wears them. Now whether you need a crew neck or v-neck t-shirt is dependent on a few factors that I’ll get into later on in this article.

If you’re like most of my clients, you’re probably wearing a t-shirt or polo shirt most of the time, so let’s make sure you look amazing in them. Before we get into that, though, I have a few bones to pick with men in regards to their t-shirts. They completely crap the bed in a few ways:

  1. Their shirts are full of logos.
  2. They don’t fit properly.
  3. The fabric is too thin, shiny, or worn out.
  4. A horrible combination of the above.

Types of T-Shirts For Men

A t-shirt is defined as:

A lightweight shirt without buttons, with short sleeves and no collar. Often made of cotton and frequently bears a picture or slogan.

Before we get into the finer points of t-shirts, let’s talk about the two different types, first. Before I started in the fashion industry, I didn’t know that there were only really two types of t-shirts. So let’s quickly get this out of the way.

Crew Neck

T-Shirts-V-Neck-Crew-Neck-Ashley-Weston-Mens-Wardrobe-Essentials-Ashley-Weston-Mens-Wardrobe-Essentials-2

These t-shirts have round collars that fit closely to the neck like the image above. You probably have these in your closet right now. They are great base items for layering or worn on their own. They work on most body types. See the below section about fit for more details.

V-Neck

T-Shirts-V-Neck-Crew-Neck-Ashley-Weston-Mens-Wardrobe-Essentials-Ashley-Weston-Mens-Wardrobe-Essentials

If your powers of deduction are strong, you’ll already know that the v-neck t-shirt is named as such because the neck is in the shape of a “v”. They also work on most body types. See the below section about fit for more details.

Long Sleeves

Long-sleeved shirts are not technially t-shirts. I put this here, because when I was first starting out, I swore that long-sleeved shirts, like Henleys, were also t-shirts. But, they’re not. Also, in my professional opinion you shouldn’t really own any long sleeve shirts. Henleys would be the only exception, but they only look good on certain body types. I’ll do an article about Henley shirts at a later time. But I don’t consider them a wardrobe essential.

If you need long sleeves, throw on a Oxford Button Down Dress Shirt, V-Neck Sweater Harrington Jacket or Blazer instead.

Logos & Designer T-Shirts

DesignerTShirt

I discussed my hatred of logos in my polo shirt article. And it definitely applies to t-shirts. Maybe more-so.

No self-respecting man should ever wear t-shirts with logos plastered all over them. We have enough billboards and advertisements in our lives, don’t turn your body into another one. Sports teams and concert/band tees are fine if worn to an event where it’s appropriate. But the worst is when I see guys wearing “designer” t-shirts. It just screams sucker, amateur and douche. Just don’t do it. If you own any of these, either throw them out right now orariGTFO

How T-Shirts Should Fit

See the T-Shirt Fit Guide for details. But I’ll quickly mention here, too, that no matter your age or body type, a t-shirt (any shirt, for that matter) should have a trim fit and lightly hug your body.

That doesn’t mean it should be skin tight, but it also doesn’t mean it should be baggy, either. A lot of my clients with larger builds tend to think that their shirts need to be baggy to hide their imperfections, but it actually works counter to that. It’ll highlight your imperfections if you attempt to hide them under larger swaths of fabric. And if you’re thinner, a larger shirt won’t add any bulk to your frame, it’ll just make you look even skinnier.

Fabric Choice

I can’t tell you how many nipples and belly buttons I see walking around town because guys are wearing undershirts or flimsy shirts with really thin or delicate fabrics as regular t-shirts.

Too Thin

I see a lot of guys wearing what looks like white undershirts because the fabric is so thin. I’ve honestly been searching for months for good white shirts that don’t show skin through. See my recommendations below.  Thin shirts/undershirts are not the same as regular t-shirts. Undershirts, true to their name, should only be worn underneath another shirt – usually an Oxford Button Down Dress Shirt or a Semi-Spread Collar Dress Shirt. They’re thin and soft because they’re purpose-built to go underneath something else.

Silky or Shiny appearance

The quickest way to look like a creepy uncle is to wear a shiny or silky t-shirt. You should only wear cotton and matte (not shiny) t-shirts. Nothing else.

Distressed or Worn out

Your t-shirts shouldn’t look like the garment equivalent of those terrible worn-out baseball caps. A t-shirt should look clean, comfortable and relatively new. Once they’ve got holes or they’re faded, even a little bit, they need to be replaced. Such is the nature of being a well-dressed gentleman. There’s nothing worse than old, stretched-out, or faded looking shirts, unless you’re deliberately going for that look.

You’ll get more usage out of your t-shirts if you wash in cold water and hang dry them. But once they’re stretched out or faded, it’s time to donate and replace them.

The Best T-Shirts For Men

Choosing the best t-shirts comes down to your body type, preference and the colors. I’ll reiterate again, because my older clients like to give me this excuse before they see the light: AGE DOESN’T FACTOR INTO WHAT SHIRTS YOU SHOULD GET – AT ALL.

Should I have V-Necks or Crew Necks?

Between the two, I would say it all depends on your preference. Some of my clients are adamant about their love or hate for one or the other. But if you don’t have a preference, I’d suggest getting one set of each. That way, you have the option to switch it up.

As for which ones you should get, there’s 3 points to consider:

  1. If you have a longer neck, go with crew necks. A v-neck would visually lengthen your neck and make it look longer. Unless you can find shorter v-necks with a shorter “v” like the white shirt on my model below.
  2. If you have a shorter neck, go with v-necks. It’ll make your neck appear a little longer.
  3. If your neck is average, the t-shirt world is your oyster and you can have whatever you want!

What colors should I have?

Every man should have these colors to start since they’ll go with everything else in your Essential Wardrobe.

  • White
  • Heather gray
  • Navy
  • Black

As for how many of each you should have, I suggest getting at least 2 of each, that way you can easily get through a week without needing to do laundry.

Best T-Shirts For Men

Designer Options

The fabrics of these options are really amazing and super comfortable. The James Perse ones are a personal favorite and I use them on a lot of my clients. I wish I could make all my clothes out of some of these materials. See my note in the section below, before making your decision. All of these shirts come in the colors I recommended above.

Ralph Lauren Cotton Jersey Crewneck T-Shirt 

James Perse Melange Cotton Linen V-Neck

Rag Bone Navy Classic T-Shirt

James Perse Grey Crew Neck T-Shirt

Brunello Cucinelli Cotton Crewnect White T-Shirt 

Budget-Friendly Options

I’d probably default to these options over the designer ones because I find very minute differences between them. The biggest factors would be fit and slightly better fabrics. I don’t find the added costs are worth what you get in return, especially because t-shirts will need to be replaced much quicker than other items in your wardrobe. All of these shirts come in the colors I recommended above. I especially love the RibbedTee shirts and the American Apparel Summer Shirts.

All Saints White Figure Crew T-Shirt

Alternative Apparel Black Plain T-Shirt

Armani Exchange Pima Crew 

RibbedTee White Rex Cotton Modal Tee V-Neck 1-Pack

J.Crew Broken-in V-Neck T-Shirt

3 Best Ways to Wear Your V-Neck and Crew Neck T-Shirts

Alternative Apparel Black Plain T-Shirt

Burberry Slim Fit Wool Trousers

Allen Edmonds Park Avenue Oxford 

Tom Ford Black Snowdon Sunglasses

IWC Portugieser Automatic Watch

Rag & Bone Duncan Shawl Cardigan

RibbedTee White Rex Cotton Modal Tee V-Neck 1-Pack

Diesel Buster 0607A Jeans

Allen Edmonds First Avenue Dress Boots

John Varvatos Lafayette Sunglasses

IWC Portugieser Automatic Watch

Brooks Brothers Camel Suede Barracuda Jacket

RibbedTee White Rex Cotton Modal Tee V-Neck 1-Pack

SIimon Miller M001 Gunnison Slim-Fit Selvedge Denim Jeans

Nike Tennis Classic Sneakers

Tom Ford Black Snowdon Sunglasses

IWC Portugieser Automatic Watch

Men’s T-Shirt Outfit Ideas & Inspiration