How To Wear and Match Colors Like A Pro

I know you’ve probably experienced that sense of dread as you’re standing in front of your closet, possibly pantless, definitely shirtless, thinking to yourself “How the hell do I figure out what shirts go with what pants?” or “How do I know which colors go well together?” So before you throw your hands in the air and wear your bathrobe to the office (not recommended, by the way), take a deep breath, I’ve got you. Here are a few of my foolproof strategies for wearing color; master them and in no time you’ll be looking sharp, feeling chill, and have your morning routine dialed in.

Keep It Simple

If you don’t know where to begin, I always say keep it simple. On the dressy side of things, that means starting with a solid white shirt and a neutral black, charcoal, or navy tie. No matter your suit or blazer color, a white shirt and one of the mentioned tie colors will work every time. On the casual side, the same holds true: a white shirt never fails. Whether it’s a basic button-down oxford, one dressed up with a blazer, sweater, or lightweight jacket for a night out, or a T-shirt paired with denim or chinos, the white shirt just works.

Go Monochromatic

Here’s another approach I like to use with my clients. Going monochromatic involves pairing different shades of the same color for a complete look. This is not only simple to execute, but it looks both cool and modern.

I recommend starting with blues or greys because they work best visually and are the easiest to execute with everyday pieces. By all means, throw in some subtle patterns (like in your shirt or tie) when layering to add a visually interesting element. I also like an all-black look, but the key to making it work is layering different textures/fabrics.

Consider Your Skin Tone

Our final piece of the puzzle has to do with your skin tone. Now I get asked all the time about matching clothing colors to eye and hair color and the only thing you need to know about that is this: it doesn’t matter one bit. Women pay attention to their eye and hair color when putting on makeup because certain colors can highlight their facial features. When it comes to men, this does not apply unless you’re wearing makeup. The only thing that you should consider is your skin color in regards to clothing choice.

Yellow Skin Tones

For men of Asian descent or those who have yellow tones in their skin, you’re going to want to avoid lighter/pastel versions of the following colors: tan, off-white, yellow, and orange. They’re only going to make your skin look sickly or muted. Solid, darker versions of these colors are ok, and from there, you can wear any other colors.

Brown Skin Tones

If your skin is on the brown spectrum (anything from light to dark) you want to avoid any brown color that closely matches your skin color. Otherwise, you’ll look dull and lifeless. Choose something darker or lighter from your skin and you’ll be in great shape. I highly recommend wearing colors like reds, yellows, greens, and blues, because they’ll look great against your warmer skin tone.

White or Pale Skin Tones

For those of you who burn at even the slightest hint of sunlight, you want to avoid reds, yellows, pinks, and oranges in all shades and forms. These colors are really going to bring out the pink undertones in your fair skin and make you look flushed or washed out. A good rule of thumb to follow is that “cool” colors are good.  Wearing colors like blues, greens, purples and their variations are going to look great against your skin and complement your fairness.

My Favorite No-Fail Color Combos

Finally, I’m going to share an easy cheat sheet with you, a few of my favorite, go-to combinations and how to wear them. It doesn’t matter if you’re wearing these casually or dressed up, all of these color combinations are going look great.

Navy and Brown

Both classic and modern, navy and brown go together like peanut butter and jelly.  From dark denim and a brown jacket or blazer to a navy suit with brown accents, to something as simple as tan chinos and a navy casual jacket, this combination is one you absolutely should master.  Throw a white shirt into any navy and brown combination for an easy way to bring it all together.

Blues and Greens

Speaking of rock-solid, one-two punches that work in tandem, blue and greens together are always on point. The wide range of hues gives you the option to dial up the statement level (or tone it down), depending on what shades you choose, what occasion you’re dressing for, or how adventurous you’re feeling.

My favorite ways to wear these colors together are:

  1. A navy suit, light blue shirt, and a green tie
  2. A blue oxford or t-shirt, green chinos, and brown leather belt with chukka boots

Black, Grey, and White

Simple?  Sure. Always sharp, clean, and in good taste? You bet. If you’re one of those guys who can appreciate the idea of a modern uniform or the utmost in classic simplicity, stick to this graphic combination and feel confident knowing you’re always going to look great.

My favorite outfit combos for these colors are:

  1. Grey suit, white shirt, and black tie.
  2. Black bomber jacket, white shirt, and grey pants.

Charcoal/Grey and Pastels

We’ve obviously established the awesome versatility of charcoal and grey, so it makes sense that they would also work well with pastels.  The great thing about pairing them with shades of grey is that their impact is taken down slightly. So, you get the benefit of a splash of color but you’re never going to be over-the-top preppy guy from Martha’s Vineyard or look like you’re on vacation in the Caribbean.

My favorite outfit combos:

  1. Grey suit, white or pastel shirt, and any simple dark tie (pastel shirt) or pastel tie (white shirt).
  2. Grey or charcoal casual jacket, pastel shirt or sweater, and navy pants.

I hope that was helpful and as you can see, wearing colors doesn’t have to be confusing or scary, so give it a shot!

2 Budget-Friendly Men’s Summer Essentials

Linen shirts and chino pants are 2 Men’s Summer Essentials that are also great if you live in a tropical, warm climate year-round. I more-than-briefly discussed them in my Summer Essentials Ebook, but since I’m about to leave on a tropical getaway (follow me on Instagram for all the fun), Dorian and I stopped by one of my favorite budget-friendly stores to show you what to get and why.

$20 – Uniqlo Premium Linen Shirt – white, light blue, light grey, and navy
$40 – Uniqlo Slim Fit Flat Front Chino Pants – navy, khaki, and white

Why I love them

  • Their linen shirts are super breathable, well-constructed, have a good, slim fit without being too slim, and they’re budget-friendly. What’s not to love? Be sure they fit according to these fit rules, though.
  • You can pair the shirts with chinos or shorts, either tucked or untucked and throw on some white sneakers, penny loafers, suede driving mocs with a casual belt and you’re good to go for casual or more dressy casual outfits.
  • The chinos have a fantastic slim fit (one of the best I’ve seen, actually) and I love that Uniqlo will hem them for free right after purchasing them in-store. There’s no other budget-friendly brand, that I know of, who does this. Be sure your chino pants are fitting properly before buying, though!

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 

Men’s Summer Essentials Ebook

In this ebook, I’ll detail the items you need for summer, why you need them, and where to get them – in designer and budget-friendly options.

These items will work very well with the rest of your year-round essentials, so if you haven’t seen that series, check it out first.

My goal is to ensure you’re comfortable, wearing appropriate colors and items for the season, while looking amazing and not like a douchebag.

So download the book, pour a glass of… something (I prefer rosé) and let me show you the good stuff!






Best Undershirts For Men

If you own any of the collared shirts I recommend in my Men’s Wardrobe Essentials Series, specifically the Oxford Button Down Shirt and a Semi Spread Collar dress shirt, you need to own some crew and v-neck undershirts. And before we get into it, there’s no scenario when you should ever wear a tank-top undershirt, AKA a wife beater – ever. You’ll see the lines underneath any shirt you’re wearing, and it just looks terrible. So let’s talk about the best undershirts for men and why you should own them. 

Undershirts are essential because

  • They provide a barrier between your sweaty, oily, deodorant-riddled skin and your dress shirts.
  • Due to this barrier, you may not have to get them cleaned as often, which will prolong their life.
  • They make dress shirts, specifically light-colored ones, look much better by not showing your skin and/or nipples through them.
  • They add another layer to your outfit for a little extra warmth or moisture wicking – depending on the weather.

How to Wear an Undershirt Under a Dress Shirt

You would think this is simple, right? Me too, but it’s very rare when a client knows how to wear an undershirt properly. A good undershirt is not something anyone should ever notice. If it’s noticeable, you’ve failed.

These are the 2 rules for wearing an undershirt:

  1. If you’re wearing a collared shirt without a tie, with the top button or two open, you need to wear a v-neck undershirt. Remember, no one should ever see your undershirt – even a bit of the collar.
  2. If you’re wearing a tie, you have to wear a crew neck undershirt. Otherwise, you’ll be able to see the v under the shirt and it looks like crap.

When should you go without an undershirt?

The only time I’d suggest not wearing an undershirt is if you’re wearing a white collared shirt. If you’re a lighter skinned guy, this is more geared toward you. Because most other undershirts might be seen through. But you can still try wearing a nude or gray undershirt to see if it’s not visible.

This problem isn’t as bad if you’re darker-skinned and wearing a similar-colored undershirt. That said, if you have darker nipples or nipples that tend to stick out a little bit, then an undershirt is required for you no matter what. Just make sure it matches your skin tone relatively closely.

Are Undershirts Supposed to be Tight?

A lot of my clients ask this question and the short answer is:
Sort of.

They shouldn’t be skin tight, but they should absolutely fit close to the body. Ideally, you want an undershirt to fit this way in the body and sleeves so you don’t see wrinkles or creases underneath your shirt. If the sleeves or body is loose, you’ll definitely see the line under the sleeves and wrinkles in the body – no matter the color of shirt you’re wearing over it.

Are Undershirts Supposed to be Thin?

Yes! They should be thin because they’re an underlayer and a thinner shirt will feel better and not add bulk to your frame. You don’t want this to happen regardless of your body type.

Should I have only white undershirts?

Not necessarily. I always have my clients wear undershirts that are closer to their skin tone. So if you’re darker skinned, you can go with a darker gray, brown, or black undershirt. Lighter skinned men should stick with light gray or white. A warning though, if you’re lighter skinned: a light gray undershirt under white or light-colored shirts is ok, but honestly, I’ve tried this a few times it and it tends to make the dress shirt look dingy or kind of faded. It’s not a good look, so I usually say to go without an undershirt in these instances.

Another quick note while we’re talking about white undershirts

I see this often with guys – if I can see exactly where your undershirt starts and ends around your neck or sleeves, (this only happens with light blue and white collared shirts), this means your shirt’s fabric is too thin and/or you need to change the color of your undershirt to match your skin tone better.

The Best White and colored Undershirts

These are the best undershirts that my clients and I love the most. Having tried all the major ones out there, these are my favorites:

Tommy John Second Skin Undershirts

Buy Tommy John’s Second Skin Crew and Deep V-Neck Undershirts

TommyJohnMensCrewNeckUndershirtsAshleyWeston12

Second Skin Crew and Deep V-Neck undershirts are my favorites. I like these a lot because they fit snugly on all body types and the fabric is super soft and has a little bit of stretch to it, so they won’t leave winkles showing through your shirts. But these niceties don’t come cheaply. Unlike their underwear, though, which I discussed here, they are very durable and will last you a good long while. They also make a nude and black colored undershirts to cover most men out there.

A quick note about their V-necks. Their images aren’t quite accurate and their titles are misleading.

Their “Deep V-Neck” is actually a regular v-neck length, so get that one and don’t waste your time with the regular v-neck, because the regular one is way too high and will absolutely be visible if you wear your collared shirts unbuttoned. I know the pictures look like the v is quite deep, but trust me, in person they’re not that deep.

RibbedTee Tri-Blend Undershirts

Buy RibbedTee’s Undershirts

 

RibbedTeeMensCrewVneckUndershirts Ashley Weston1

RibbedTee makes some of the softest, most comfortable undershirts I’ve tested. My clients said it was like wearing a soft fluffy layer of air. Their gray undershirts are great for lighter skinned guys, too, but they make many colors. You honestly can’t go wrong with any of their undershirts, but my clients were partial to the Tri Blend, Supima cotton and their Evo Tencell ones.

Calvin Klein Undershirts

Buy Calvin Klein Undershirts

CalvinKleinMensCrewandVNeckndershirts Ashley Weston12

For a budget-friendly option, I really like Calvin Klein’s Cotton Classic undershirts because the fit is great and the fabric is not too thick or thin, which is a problem with most other undershirts in this price range.

I like them because they also have different fits based on your body type – like slim and regular – which fit my larger or taller clients very well. They also make a similar undershirt to Tommy John called Body Modal, but I say just spend the few extra bucks and get the Tommy Johns instead because they’re just all around better.

Spanx Undershirts

Buy Spanx Cotton Compression Crew & V-Neck Undershirts

SpanxCrewVneckMensUndershirts Ashley Weston

I mentioned these in one of my AskAW videos because my clients who wear these LOVE them. If you’re looking to slim down your waist, belly or chest area, these are perfect. I like to say that they are like visual airbrushing tools. They’re not so snug that it feels like you can’t breath, which is important because I think a lot of men assume they’ll be too restrictive, but they’re just a little bit tighter than your average shirt, but they will literally drop you down a waist or shirt size in most cases.

Alright, that’s it. Those are the best undershirts for men – period!

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

How Should A Polo Shirt Fit?

If I had a dollar for every poor-fitting polo I’ve seen, I’d have my own moneybin! So let’s make sure you look amazing while wearing your polo shirt. As I always say, these rules apply to any man, no matter your age or body type. 

Collar & Neck Opening

The size of the collar isn’t something you need to be concerned with as they’re pretty standard across all brands. Just make sure they’re not too small.

However, do pay close attention to the buttons – specifically, you want to make sure the buttons end no further than the top of your armpits. Anything past that, like the image below, is too long and will look like a super deep v-neck when un-buttoned – not good.

Ashley Weston Long Polo Shirt Buttons

Wearing a polo shirt with the top 1-2 buttons left unbuttoned will help frame your face better and make it look great. So when trying on a polo shirt for the first time, make sure to unfasten the top 2 buttons, regardless of whether it’s a 2, 3 or 4 button polo, to see how the neck opening sits on your body. You don’t want the collar/opening to lay completely flat on your chest like this:

Polo Shirt unbuttoned bad Ashley Weston

You want it to stand up a little bit and have some structure like the image below. But the inverse of that, is you don’t want it so stiff that even when unbuttoned, it doesn’t spread out a little bit.

Polo-Shirt-Collar-Ashley-Weston-Mens-clothing Fit guide

All of images of the different ways to wear a polo shirt in my Essential Polo Shirt Video & article have the perfect neck opening and button placement.

Sleeves

The sleeves should hit around mid-bicep and lightly hug your arms. Some polos have a ribbed band at the end of the sleeve where it’ll hug a little tighter, which is fine, as well. Regardless of this, the sleeves shouldn’t be too tight where it looks like your biceps are being strangled. You also don’t want there to be bunch of slack or room around the bicep, either. That just looks cheap and tacky and makes your arms look really small in the worst way possible. If the polo fits well everywhere else, have your tailor slim them down to fit your arms better.

Sleeves Polo Shirt Ashley Weston

Body/Torso

Like I say in all my shirting articles, the perfect fitting polo will be when you can pinch (not pull) between 1 to 2 inches of fabric on either side of your stomach. This goes for EVERY SINGLE BODY TYPE. A lot of my larger clients fight me on this… until they see how awesome it looks. The “Like This” image above has the right amount of fabric to pinch.

Length

The shirt should end somewhere between upper to mid crotch. I would rather it be closer to mid-crotch than upper-crotch because this avoids showing stomach when reaching up for things and allows it to be lightly tucked into the front of your belt/pants to break up your proportions – if you want.

Crotch Measurements

Tails

Luckily, most designers are getting rid of tails, because I don’t really like them anyways. But if you have a polo shirt that has a tail, make sure the back part is no more than 2 inches longer than the front. Even then, I’d advise you to get a polo without a tail, because 99.9% it doesn’t look so great.

Best Polo Shirts For Men

See my Polo Shirt Essential Article for my favorite polos that every man should own.

The Polo Shirt

A Polo Shirt is a great, versatile item that I put all my clients in at some point of us working together. They’re timeless and a cornerstone of any good spring or summer outfit. I often recommend wearing them in place of t-shirts, as they give a casual outfit a bit of polish – which is never a bad thing. No matter your age or body type, every guy needs a few polo shirts in his wardrobe.

A good polo shirt will:

  1. Fit like a glove.
  2. Enhance the good parts of your physique and hide the imperfections.
  3. Make you look more polished and put together.
  4. Layer incredibly well.
  5. Only have short sleeves – long sleeved polos have no place in your wardrobe.

Fabric

Fabric choice is the biggest thing to consider when choosing a polo shirt and heavily dependent on your body type. The fabric you choose will determine how good (or bad) you look in a polo shirt.

Piqué Cotton

Piqué cotton polo shirts are made with cotton yarn and have thin ribbing visible in the garment. The texture is soft, and if you look closely you can see the tightly raised cords that give a waffle-like appearance.

Piqué polos are best for heavier-set men with wider physiques because the textured fabric hugs the body without conforming to the less flattering areas of the chest and stomach. When I’m working with a client who’s worried about his belly being accentuated, I always go with pique cotton. Think of the fabric as airbrushing your torso and hiding the problem areas.

Check out how much more flattering the piqué cotton polo is on the same guy compared to a cotton/silk blend polo. I bet his hands are covering his belly button divot in the cotton polo shirt picture, too. It’s an old photographer’s trick. Notice his chest area looks a little more smoothed out? Please don’t think I’m recommending this polo, it’s pretty bad (that’s a horrible sleeve length) but it highlights the “airbrushing” effect that piqué cotton has very nicely.

Pique Cotton Vs Cotton or Silk Blended Polos Ashley Weston

Cotton & Cotton Blended Polos

If you’re in decent shape, skip the piqué polos and grab a few cotton/cotton-silk blended polo shirts. The material looks better on your body type and is softer and more comfortable than pique cotton. These polos have a sleek, modern look that are great on their own or underneath a jacket. Beware, it’ll shine a spotlight on your body’s imperfections if you’re not in good shape!

SilkBLendPolo - Ashley Weston

Colors, Patterns, Piping, Etc.

Avoid any patterns or collar/sleeve piping and stick with the basic (and best) colors to begin. Grab a few white, black, navy, and charcoal/gray colored polos. They’ll give you the most versatility with the rest of your Essential Wardrobe and will work with any skin tone and body type.

If you’ve got the basic colors already, definitely get some brighter colors that compliment your skin tone and/or throw some stripes in there, too. I would universally avoid plaids or any other wackier patterns, it’s just too much and looks tacky.

To Tuck or Not To Tuck

If you’re wearing a polo shirt without a jacket, then don’t tuck your shirt into your pants. I know golfers do this, but you’re not on a golf course and it looks horrible tucked in.

If you’re wearing a jacket, then loosely tuck in the front part of the shirt by your belt buckle like in my 3 ways to wear images below. The shirt should still cover the top half of your belt buckle – you don’t want to completely see the buckle. I love doing this on my clients because it breaks up the outfit when you see a little of the belt buckle and gives it a little polish without overdoing it.

Leggo my Logo

Please don’t get a shirt with a huge logo all over it. Just. Don’t. Logos that are small and the same color of the rest of the shirt are passable, but if you have the option, go logo-less.

How Should A Polo Shirt Fit?

Check out my Men’s Polo Shirt Fit Guide for details.

The Best Polo Shirts for Men

Designer Options

For a pique polo, I recommend the Sunspel Riviera Polo Shirt. This shirt was made for Daniel Craig as James Bond in Casino Royale. A black or navy polo pairs well with either dark wash jeans or grey wool trousers. For a silk/cotton blend polo shirt, I love John Varvatos and Burberry. The shirt’s impressive construction and fit is well worth the price.

John Varvatos Hampton Polo 

Sunspel Charcoal Jersey Polo Shirt

Ermenegildo Zegna Mercerized Cotton Polo Shirt 

Burberry Navy Silk Cotton Polo

Theory Black Boyd Polo

Budget-Friendly Options

I’m a big fan of H&M’s cotton polo shirts. Actually, I would probably get those over the designer options a majority of the time. They won’t last forever, but they’re cheap enough to replace every season or two. They have a clean design with a great fit and a price that you can’t beat. The model in the first picture below is wearing the H&M Polo.

H&M Polo Shirt 

Uniqlo Navy Dry Pique Short Sleeve Polo Shirt

J.Crew Black Pique Cotton Polo

3 Ways to Wear a Polo Shirt

(Sunglass lenses sold separately)

H&M Polo Shirt

J.Crew Broken-In Chino in 484 Fit

Vans Authentic Sneakers

True Vintage Revival Glasses 

Polo-Shirt-Outfit-2-Ashley-Weston-Mens-Wardrobe-Essentials

The jacket and chinos are actually from Dsquared2, but they’re for an upcoming season and not available in stores at the time of writing. So I added the best substitutes below.

Philipp Plein Coat So Cool

Ermenegildo Zegna Mercerized Cotton Polo Shirt

Brooks Brothers Slim Fit Dark Khaki Garment-Dyed Chinos

Nike Tennis Classic Sneakers

Allen Edmonds Black Poplar Belt

IWC Portugieser Automatic Watch

John Varvatos Lafayette Sunglasses

 

Polo-Shirt-Outfit-3-Ashley-Weston-Mens-Wardrobe-Essentials

Burberry Modern Fit Wool Part Canvas Jacket 

Burberry Silk Cotton Polo Shirt 

Levis Chino 511 Slim Fit Jeans 

Salvatore Ferragamo Penny Loafer Shoe

Allen Edmonds Brown Poplar Dress Belt

Piaget Altiplano Watch

John Varvatos Lafayette Sunglasses

Outfit Inspiration