10 Biggest Style Mistakes Young Men Make

As a stylist, my clients range anywhere from teenagers all the way up to men in their 60s and 70s, and these are 10 mistakes I’ve noticed with my younger clients when I first start working with them. The road to finding your own personal style is a long one but keep these in mind as you’re figuring out your own path!

10. Ill-fitting clothing

Whether you’re on the thin side or are a bigger guy, your clothing should always fit properly. A lot of times many young men try and over-compensate in either direction to make up for what their body type is, but don’t do it.  Big or small, proper fit is always king.

9. Oversized ties and knots

Buying a tie that’s too wide and using massive knots will only serve to make you look like a little kid, so make sure you use a knot that’s proportionally sized for your frame and suit.

8. Trying to be a hypebeast all day, everyday

Focusing solely on brands and labels plastered all over you is only going to send the signal that you’re dressing for the wrong reasons.  Be judicious in your brand choices and know that understated is always going to look good.

7. Dressing well means being uncomfortable

Thinking that you can’t dress well and be comfortable at the same time is something that I get all the time and it drives me crazy! A properly fitting shirt or jeans should always be comfortable and flattering.  Are they going to be as comfortable as baggy sweats and an old t-shirt? No, but ultimately if you want to be taken seriously you should always be cultivating and presenting a thoughtfully stylish appearance to the world, not one focused only on comfort.

6. Buying all statement items

This is a problem for most men looking to dress better, but more often with younger men because I notice they confuse fashion with style. Fashion pieces can be loud and make a statement, but that doesn’t make you stylish. Here or there, sure, it’s fine, but it’s important to always have basic, foundational items that are stylish and versatile as well.

5. Not having a foundational wardrobe

Speaking of the foundational basics, it’s critical to always start with the basics and get the right jeans, t-shirts, button-ups, shoes, and sweaters first. Don’t underestimate the style and power of a sharp, basic wardrobe as the building blocks of great personal style.

4. Dressing exactly like your friends and not trying different things

Going along with following hypebeast trends, I see a lot of men fall prey to dressing just like everyone else in their squad. You’re young, have fun with your clothing and style and embrace your individuality. Figuring out what looks good on you and makes you feel best is an important step in figuring out your personal style.

3. Looking good is expensive

One of my least favorite misconceptions about style is that unless you’re rich, you can’t look good, and that money matters in dressing well. This couldn’t be further from the truth! Looking good on a budget is absolutely doable, no matter how low the budget, and it just takes some knowledge and focusing on well-fitting, basic items.

2. Mixing too many patterns and colors

Just like focusing only on statement pieces, many younger men confuse being loud and wearing excessive patterns with being stylish. But in reality it’s just the opposite. Focus on more subtle details and cohesive pieces to give your outfits the best look.

1. Not caring how you look

This applies not just to clothing, but to grooming and hygiene as well. If you focus on looking relatively clean and well-groomed you’ve beaten a majority of young men out there.  Anyone that makes fun of you for caring about your appearance is a lost cause, so don’t even worry about the haters.

As I said earlier, don’t forget that personal style is a journey and like any journey, it’s bound to have a few bumps along the way, the important part is learning from your mistakes and figuring out what works best just for you.

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 

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.

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.

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 & 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.

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?

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.