3_Ways_To_Wear_A_Henley_Shirt_Longsleeve_Shortsleeve_Men_Ashley_Weston

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 

AskAW9 Wordpress

THE #ASKAW SHOW: EPISODE 09 W/ Andrew Snavely FROM PrimerMagazine.com

In this episode, my special guest – Andrew Snavely from PrimerMagazine.com answer some of the most scintillating questions for the readers/viewers.

Have a question you’d like me to answer? Ask in the comments of the above youtube video or send me an email.

In this episode, we answer:

Q: I’ve lost a significant amount of weight and now all of my clothes are clownishly large on me. Can a tailor make my clothes fit again or should I just buy all new ones?

A: See the video above for the answer and my men’s clothing fit guide for how your clothes should fit.

Q: I watched your T-Shirt video and if I have a nice looking tee with a pretty minimalist design, does that hinder a look the same way a straight up graphic tee would?

A: Short answer – sort of. See the video for the longer answer.

Q: As a shorter man (5’6″), I find it difficult to find stuff that fits me and looks good. I was hoping you can provide some general style tips for shorter men.

A: See TheModestMan.com for a great site for shorter men style. But in our experience, as long as your clothing fits properly, there’s not much else to worry about.

Q: I recently picked up a Briefcase in a navy/ tan leather color way, would I match my wallet/watch/belt/etc. To the bag? What would you do in my situation?

A: Don’t think about it too much. Andrew is less of a stickler here, but I am more of a stickler. See video for details.

T-Shirt-Ashley-Weston-Mens-Clothing-Fit-Guide-4

How Should A T-Shirt Fit?

Just like with polo shirts – if I had a dollar for every poor-fitting t-shirt I’ve seen a man wearing, I’d have two moneybins! So let’s make sure you look amazing in your t-shirts, as well.

When I first start working with clients, I always get pushback when I utter the next sentence, but they later admit I was right when they’re getting complimented all the time.

These rules apply to all men, no matter your age or body type. So trust me on these rules. I’m here to make you look amazing, not like some doofus who’s trying too hard.

Neck Opening

Crew necks are pretty standard, but just make sure it doesn’t fit too tight around your neck, or too loosely. If the collar looks stretched out or you can see some of your shoulder when wearing, that’s too loose.

If you’re wearing v-necks, you need to avoid deep v’s at all costs. Man cleavage is just… no. Some brands will have deeper v’s than others, so be wary of how deep it is. Just make sure the bottom point of the “v” doesn’t go past the top of your armpits and you’ll be fine.

Sleeves

Crew Neck T-Shirt Fit Guide Ashley Weston

The sleeves should hit around mid-bicep and lightly hug your arms. The sleeves shouldn’t be too tight where it looks like your biceps are being strangled. The image below has sleeves that are perfectly hitting the right place and hugging the arm to perfection.

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 t-shirt fits well everywhere else, have your tailor slim the sleeves to fit your arms better. I have to do this with clients all the time.

Body/Torso

Armani Exchange Grey Pima V-Neck Tee

Like I say in all my shirting videos & articles, the perfect fitting t-shirt will be when you can pinch (not pull) between 1 to 2 inches of fabric on either side of your stomach, like the image above. This goes for EVERY SINGLE BODY TYPE. A lot of my larger clients fight me on this… until the compliments start rolling in. 🙂

Length

Crotch Measurements

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.

The Best T-Shirts For Men

See my T-Shirt Essential Article for my favorite t-shirts that every man should own.

Ask AW Show Episode 06 - First Date Advice, Clothing for Muscular Men

The #AskAW Show: Episode 06

In this episode, I answer these questions:

Q: What was your “big break” in the fashion industry?

A: I talk a little bit about it here, as well.

Q: What is the most important thing to keep in mind on a first date?

A: I actually have a whole long story about this in my free 10 Style Mistakes ebook. It gave me the inspiration to write the book!

Q: I work out and am having a hard time finding clothes that fit me properly. What can or should I do?

A: Get your clothes tailored to fit your body type properly. See the video for details, as well.

Have a question you’d like me to answer? Ask in the comments of this youtube video or send me an email.

Chino Pants Mens Clothign Fit Guide Ashley Weston

Chino & Khaki Pants Fit Guide

Chino & Khaki pants, you know them, you love them, as do I. Now let’s get into how they should fit, regardless of your age or body type.

To see my Chino & Khaki Pants rules that most guys break, see here.

Waist and Seat

Like all your pants, they should fit perfectly around your waist with no need for a belt to hold them up. For chinos, the waist will sit lower than suit pants, but should hit exactly where the waist of your jeans should be – right in between the upper and mid hip-bone area. The image below shows jeans hitting perfectly in the mid-hip bone area. Anything below that will look terrible and sloppy.

Waist2

The butt area, AKA the seat, should lightly hug your butt and not be saggy or very tight. If it feels like you’ll split your pants when you sit or bend down, they’re too tight. If it looks like you’re carrying a full load, you should probably try a different fit or brand. if that doesn’t work, you may also be able to go down a size and see if that fixes the issue. And if that doesn’t work, you can get need get the upper thighs taken in by a tailor to compensate for the extra room in the seat. Just a warning, though, this will cost so much that you can likely get a new pair of chino pants for the same price.
RealMenRealStyle has the perfect illustration of how the seat of your chino pants should fit:

Seat-Suit-Pants-Fit-Ashley-Weston

Legs

Thighs

They shouldn’t fit too tight, but lie comfortably close without feeling like it’s pulling at the knees when you walk or bend down. Unlike jeans, you want a little more room in the thighs. You should be able to pinch a minimum of 1 inch of fabric, but no more than 1.5 inches on either side of your thigh. If you can pinch more than that, try a different style or brand or, if possible, go down a size. As a last resort, you can get a tailor to slim the legs to this size, but just like taking in the seat of your chinos, it’ll probably cost more than buying a whole new pair of pants.

ThighPinch

How long should chinos or khakis be?

A lot of (older) guys think their chinos should fit like long drapes on their legs. Unlike jeans, wool pants and trousers and suit pants, you want your chino pants to be hemmed to leave a slight or no break. Also, unlike your wool trousers, you want them to be hemmed straight across instead of slightly longer in the back.

If you’re thinking about going sock-less with your chinos, then go with a slight break. This enables you to switch it up – if you want a no-break or cropped look, you can just roll them up and unroll them when you don’t want that any longer. It gives you a little more flexibility and versatility.

The gentleman in the right image, wearing sand colored chinos, has no break/cropped pants. The fella on the left is wearing his chinos with a slight break.

The Best Chino & Khaki Pants For Men

See my Men’s Wardrobe Essentials: Chino Pants article and video for my favorite pairs of chinos & khaki pants you should own, regardless of your age or body type.

Polo-Shirt-Ashley-Weston-Mens-Clothing-Fit-Guide

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.

How Should Dress Pants and Wool Trousers Fit Ashley Weston

How Should Dress Pants and Wool Trousers Fit?

The short and honest answer for how should dress pants and wool trousers fit is that they should fit exactly how your suit pants should fit, so if this article looks familiar,that’s why. This advice goes for any of these pants: slacks, dress pants, wool trousers, wool pants, whatever you want to call them. Since this is a fit guide, I won’t get into fabric weights here, but it’s a very important point when choosing your dress pants/wool trousers that won’t be worn as part of a suit. See my Wool Pants & Trousers article for details.

Waist and Seat

Dress pants and wool trousers should fit perfectly around your waist with no need for a belt to hold them up. They should hit around the high hipbone area, or even slightly higher. You do not wear wool pants at the same waist as jeans – which are usually designed to sit lower. Saggy pants is a big no no.

The seat, or butt area, should lightly hug your butt and not be saggy or super tight. If it feels like you’re going to split your pants, they’re way too tight. If you’ve got a bunch of extra fabric around the butt, they’re much too loose. A tailor can fix this, it won’t be easy or cheap, but if everything else on the pants fits properly, definitely get it done.

RealMenRealStyle has the perfect illustration of how the seat of your pants should fit:

Seat-Suit-Pants-Fit-Ashley-Weston

Legs

Thighs

You want to be able to pinch around 1/2″ to 1 inch of fabric on either side of your thigh. If it’s less than that, your pants are too tight. If it’s more, have your tailor slim the thighs.

Knee to Ankle

If you’re a thin to regular build, the pants should have a slight taper so that it gets narrower towards the ankle, like the image below. This will look great on this body type/size.

Legs-Ashley-Weston-Mens-Clothing-Fit-Guide

If you’re a thicker/wider guy, you want the pants to be cut straight down from the knee to the ankle – like how your jeans should fit. This will balance your proportions nicely. If you went with a taper here, it’d make you look very top-heavy.

Dress Pants Wool Trouser Fit Ashley Weston

Hem & Cuff

Always default to having your pants hemmed to leave a quarter (also called slight) break. It looks more polished and sharper than a full break and no break at the hem is a time & place kind of thing, and not generally for everyday wear. A slight break works for everyone.

A trick I do with all my clients is to have the tailor hem the pants so that it’s slightly longer at the back of the hem. That way, when you’re walking, you’ll show less sock and when you’re standing still, it’ll lay nicer on the top and back of your shoe.

There are very few times, I’d argue almost never, when you’d cuff your dress pants or wool trousers. I’ve never cuffed pants for a single client because it’s not necessary, no matter their body type.

If you’re not familiar with the different type of pant breaks, PrimerMag has some great images to help you understand:

PantsFit_Breaks-2

The Best Wool Pants And Trousers For Men

See my Wool Pants and Trousers Essential article for my favorite wool pants for men.

The Best Ways to wear Dress Pants & Wool Trousers

See the bottom of my Wool Pants and Trousers article for details.

How-Should-A-Sweater-Fit-Header

How Should A Sweater Fit?

A lot of my clients ask me how should a sweater fit, so I figured it was time to write down my typical answer so you can understand this, as well. These fit rules apply to any sweater, but I’ll use a v-neck sweater in my images below to demonstrate how a sweater should fit on a guy.

A quick note before we begin: Most sweaters are made of cotton, wool, cashmere or blends with other fabrics. This is a problem for tailors because the fabrics are fragile, which makes them very hard to work with, so you should find a sweater that fits you perfectly off the rack, as it’ll be very difficult, if not impossible, for a tailor to fix a majority of sweaters. The only exception are cotton crew necks. Those can easily be tailored.

What do I wear under a V-Neck Sweater or Crew New When Trying On?

It’s important you’re wearing the proper shirts when trying on your sweater so you can get the proper fit.

V-Neck Sweater

When you’re trying on a V-Neck sweater, you should only be wearing a Dress Shirt or Oxford Button Down Dress Shirt because these are the only two shirts that you should ever wear under a v-neck sweater. That means no t-shirts, polo shirts or any other kind of shirt. Just a collared shirt.

Crew Neck Sweater

When trying on a crew neck sweater, you should only be wearing a t-shirt or v-neck shirt because that’s all that should be worn under a crew neck. You might be able to get away with a collared shirt, but it’s not my preference to wear them with crew necks because it usually looks pretty bad.

What a Sweater Looks Like When its Too Small/Tight

I want you to see what a sweater looks like when it’s too small. See the points below for details.

How Should A Sweater Fit TooSmall

  1. Shoulders – If he pulled the sweater shoulder up so his shirt collar was tucked under the sweater collar, the seams would be sitting on top of his shoulders, which means its way too small. You can kind of see the seam sitting way too high on his shoulder on his bent arm side.
  2. Arm Hole – Way too tight, you can see it bunching underneath his armpit. I guarantee it’s incredibly uncomfortable.
  3. Neck/Collar – If he pulled the sweater so the collar was touching his shirt’s collar, the “v” of the neck would go down past the top of his armpits.
  4. Sleeve Length – The sleeves are way too short, which is why he has them pulled up on his forearms in this picture. I know this because (See the next point)
  5. Body Length – The body length is about 2 inches too short. At the shortest point, a sweater should hit past the bottom of your belt buckle.

What a Sweater Looks Like When Its Too Big

How Should A Sweater Fit Too Big

  1. Shoulders – The seams are way past where his shoulder starts sloping down and are just resting on the upper part of his arms – not good.
  2. Arm Hole – Way too big, so it’s making his chest look super wide and baggy with all that extra fabric around the chest area.
  3. Neck/Collar – You can tell it’s too large because you can see his shirt on the sides of his collar. If he pulled the sweater forward, so the “v” rests better against his shirt collar, the “v” would go past the top of his armpits.
  4. Sleeves – They’re hard to see because his hands are in his pockets, but with everything else not fitting properly, I’m sure the sleeves are way too long and not ending at the bend of his wrist. Also, they’re way too big and baggy, which just look floppy and wrinkled in odd places.
  5. Body Fit and Length – I bet if he pulled his hands out of his pockets, the sweater would be way too long and go past the 2 inch mark below his belt buckle. As you can see, there’s excess fabric on both sides of his torso because the sweater is just to big.

How long should a sweater be?

A sweater should end somewhere between just past your belt buckle and no more than 2 inches past that. In a lot of my other fit guides, I usually differentiate the length based on your height, but for a sweater it doesn’t matter. It should hit between those two points for everyone. This goes for all sweaters.

how should a sweater fit

Sleeves

Length

While wearing the sweater – when you bend your wrist, so your palms are facing the ground, the sleeves should end where your wrist ends. So where the white shirt cuff stops in my picture below. A sweater’s sleeves shouldn’t be totally smooth and ripple-free – if it is, that usually means it’s too small. It’s impossible for a sweater to fit like that, so don’t bother trying. Just make sure it ends at the bend of the wrist and not before or after.

Sleeve-Length-Ashely-Weston-How-Your-Suit-Should-Fit

Fit

The sleeves should fit close to your arm, but not so tight that you can see your muscles or the ripples of the shirt underneath (like the sweater that’s too tight above) or so loose that it’s floppy and folding on itself. The model I used was very muscular, but you can’t see his biceps well-defined, or the folds of his collared shirt under the sleeves.

Quick tip: If you’re wearing a v-neck sweater, lightly tug on the sweater sleeve so your dress shirt cuff is sticking out about 1/4″. It’ll have a little bunching near the wrist, that’s fine. As you can see in my picture below, it still looks great.

V-neck-sweater-header-Ashley-Weston-Mens-Wardrobe-Essentials

Shoulders

Like with all your garments in the Essential Series, you want the shoulder seams to hit just where your shoulders start to slope down into your arms. I call this “the natural end of your shoulder”. See the picture below for what I’m talking about – the seam hits perfectly at the point where the shoulder turns into the upper arm.

how should a sweater fit

Body

For any sweater, you want to be able to pinch no more than 2 inches of fabric on either side of your lower rib cage. You also don’t want to be able to pinch any less than 1 inch of fabric, as that’s way too tight. You want it to lightly hug your torso, but not be so loose or tight. This goes for ALL BODY TYPES. I know some of my larger clients fight me on this, but they always come around when they see how much better and fitted it looks. A little rippling in a sweater will always happen, so it’s unavoidable.

Collar

This only applies to v-necks, as crew neck sweaters are all pretty universal. You want the bottom of the “v” to be no lower than the top of your armpits.

Neck Opening

The opening of the v-neck should be just wide enough so that you can tuck your collar tips and they stay in place – like the image above. A wider opening than that would look terrible, as it’ll show too much shirt on the outside of the collar like the image of the too big sweater. For crew necks, they’re a pretty standard size – they shouldn’t be stretched out or show any shirt underneath.

Armholes

They shouldn’t be so high that they’re cutting into your armpits like in my “too small” image or so big and low that it looks like a bunch of excess fabric is around your chest like in my “too big” image near the top of this story.

The Best Sweaters Every Man Should Own

See my V-Neck Sweater Essential Article for my favorite sweaters that every man should own.

Credits

Photography: Justiin Charles
Model: Joseph Boyd at Wilhelmina Models
Hair/Makeup: Brendan Robertson for Exclusive Artists Management using Clarins Skincare and Kevin Murphy Hair Care