How To Tie Scarves For Men - Ashley Weston

How To Tie Scarves for Men

This article is part of my Quick Tips series.

I see a lot of articles and videos about all the possible ways of tying a scarf, but honestly they’re mostly useless, ugly or both! So these are the 4 best ways for how to tie scarves for men and how I tie scarfs on my clients for cold weather events or publications like GQ & Esquire. Throw out all the other ways to tie scarves, they’re a waste of time!

A quick, note about length, material and patterns

This and socks is one of the few places where you really can’t go wrong with any choice. So I always tell my clients to have at it and choose anything they think looks great, it’s a perfect way to show off your personality. So any colors, patterns, materials and lengths that you like, go for it! You can’t go wrong here.

Here’s the 4 best ways for a man to tie his scarf.

The Drape

TheDrapeThis way of wearing a scarf is perfect for those who don’t like anything wrapped around their neck but still want to keep warm. I like it because it’s easy to do and it looks nice. It doesn’t do too much to keep the front of your neck warm, but it does keep the back of your neck as well as the side of your coat nice and insulated.

Definitely wear this underneath your jacket or coat, it’ll keep it in place. Otherwise, it’ll move around a lot as you walk.

  • Take the two ends of the scarf, have them hang equal length on either side of your neck.
  • Now simply tuck in each side of the scarf under each lapel of your jacket or coat. It seals in the small gaps between your chest and coat to keep you nice and warm.

The Wrap

TheWrap3It’s a pretty standard way of wearing a scarf. You probably wore yours like this as a kid and it’s just fine for men. It’ll do what The Drape won’t do – keep the front of your neck warm.

  • Start by putting the scarf behind your head and lowering one side to be twice as long as the other.
  • Now wrap the longer side once around your head. The ends can be equally long or uneven. It doesn’t matter.
  • Tuck the excess under your collar or lapel, if you want.

The Loop

This is my absolute favorite way to tie a scarf on a man and the warmest way to tie a scarf. When I see men on the street wearing a scarf like this, I think it just looks so damn sharp! You can’t go wrong with this way of tying a scarf.

  • Fold the scarf in half.
  • Wrap it around the back of your neck.
  • Tuck the loose ends through the loop created by the other side of the scarf.
  • Adjust to desired tightness.

The Bib

The Bib How to tie a scarf Ashley WestonThis way of tying a scarf tends to look best with longer scarves, but you can get away with it if you’re using a shorter one, too.

  • Put the scarf around your neck, making both sides equal in length.
  • Cross the two ends.
  • Push one side up and under the other.
  • Pull it tight (but not too tight—breathing is important even in winter!)

That’s it! Those are the best (and only) ways for a man to tie a scarf.


The Harrington Jacket

This article is part of my Men’s Wardrobe Essentials series.
Timeless, casual, cool and sexy. It doesn’t matter if you’re old, young, running errands, or hitting the links – you need a Harrington jacket. It’s light and pairs well with nearly anything. This iconic jacket will never let you down.

Popular since the ’50s, the Harrington jacket was worn by pretty much every iconic star of yesteryear: Elvis Presley, James Dean, Steve Mcqueen, and most recently, Daniel Craig as James Bond. The Baracuta G9 is the O.G. worn by these stars and is still made today, but there’s a lot of great brands making them.

Lightweight, often teflon-coated cotton, standing collar, zip front, and the tartan lining, I just love the hell out of this jacket. The original Baracuta brand is a bit tough to find, but Fred Perry and Ben Sherman make killer versions that I actually prefer.

Why you need a Harrington Jacket

Lots of guys, my clients included, have a tough time finding a casual jacket that isn’t too sporty or dressy. A Harrington Jacket fills this gap perfectly.  It looks great with jeans and sneakers as well as dressier items like collared shirts and wool pants.

The fit and design is also very flattering on any body type. On top of that, the style hasn’t really change since it’s inception and with proper care, this jacket will last decades – easily. The mileage and value you’ll get from this jacket is some of the best for any menswear item I’ve seen.

Which Harrington Jacket Is Right For You?

Since we’re talking about essential/foundational pieces and the style of these jackets is pretty standard across brands, you really only need to worry about the color, which is simple: get a navy Harrington jacket.

If you’re a regular to slim build, you can pull off other colors, but your first Harrington should be navy. If this is your second Harrington, definitely go for a khaki color.

I don’t recommend other colors, like black or burgundy, because they’ll be much harder to match with other items in your Essential Wardrobe and/or it’s just a big swath of color. So if you went with black, it’s a lot of black and, I think, doesn’t look all that great in person. It looks much better in photos than in real life.

One small note: If you’re a larger build, you may not fit Ben Sherman, even their larger sizes tend to run pretty slim.

The Best Harrington Jackets To Own

Designer Options

My personal favorite is the Fred Perry jacket. It’s what I use for all my clients.

Budget Friendly Options

3 Ways To Wear




Outfit Inspirations


How Should Dress Shoes Fit?

This article is part of my Men’s Clothing Fit Guide.

I’ve seen so many articles and videos taking how to get the proper dress shoe fit that are completely unnecessary and just create more useless work and steps for the poor readers. Of course, if you ask a shoemaker or shoe salesperson about what goes into fitting for a pair of dress shoes, they’ll tell you about the painstaking process you must endure as they pull out their Brannock device and start measuring the length of every toe hair in relation to the current barometric pressure. As someone who dresses and fits men for shoes as part of my career, it’s all hogwash.

Never once, in all my years, with all my clients, have I ever needed to get an exact measurement of their feet – and this is because the brands and manufacturers don’t work this way. Their sizes aren’t universal and can vary wildly between brands. So a 9 in one brand might fit the same as a 10.5 in another brand. Each one is different, so it’s great that you know your right foot is 10.236 inches long by 4.789 inches wide, but that really doesn’t matter unless you’re getting custom made shoes.

So what you have to do is try on dress shoes and figure out how to get the best fit in that style/brand. Let me show you how.

Before Trying On Dress Shoes

You should know and do these few things before trying on dress shoes.

1. Know Your General Shoe Size

I’m assuming you’ve worn shoes before and have a general idea of your size? Great! That’s all you need. Like I said earlier, since each manufacturer has different fits and sizing for their shoes, it’ll all be trial and error anyways. The thing you want to do is get in the ballpark and use that as a starting point.

2. Dress shoes should fit perfectly the first time you try them on

If they don’t, they’ll never fit. Leather, especially in dress shoes, will stretch very, very little, so “working in” a pair of dress shoes is not going to happen and will be a waste of your time and money. One of the worst things ever is wearing a pair of uncomfortable shoes – as a woman, I know this all too well!

3. Your feet swell throughout the course of the day

So, if you can, try on shoes in the afternoon. This way, you’ll get the most realistic size and fit of the shoes.

4. Your feet are not the same size

Make sure the shoes fit your larger foot first, not the smaller one. Slightly too big is not uncomfortable, slightly too small is very uncomfortable.

How To Try on Shoes

When you’re trying on shoes, here’s the things to do and look out for.


Wear the type of socks that you will normally wear with these shoes. In other words, don’t wear your thick woolen socks, or your super thin ankle socks when trying on dress shoes.


If you feel ANY bunching in the toes or feel the shoe pressing against any of your toenails, they’re too short. I see some places talking about your toes grazing the front of dress shoes – this is not correct.

Your feet shouldn’t be touching or grazing anything in the front. If they’re grazing, that means when you walk, your toes will be jammed into the front of the shoe, because your feet will shift slightly forward as you walk, which is very uncomfortable. Either go up a half size and if that doesn’t fix the problem, it might be a style or width issue. So try a different style or a different brand that makes the same style. Luckily, with dress shoes, they’re pretty darn similar, so you’ll find an equally great one, I promise.


The shoe should not be putting any pressure or squeezing on the sides of your foot – anywhere. If you feel anything like that, you may need to go up half a size and see if that fixes the issue. If it doesn’t, you can see if they make a wider size in the same style. If they don’t, then try a different style or brand. Some brands are wider than others.

On the flip side side of that, you also shouldn’t have any room on either side of your foot that allows your foot to move left or right when it’s laced up. If this happens, go down half a size and see if that fixes the issue. If not, you can ask if they have a narrower width in this shoe. If not, you may need to try a different style or brand.

The average man has a medium width of D. If a brand doesn’t specify a width, which most of them don’t, this is probably the width they use. Again, though, a brand’s definition of a D width varies, so watch out for the differences. A narrow width is a B, a wide width is E and an x-wide width is 3E.

If your foot falls between a B and a D, go with the larger width.

I see some places saying that if they’re lace-up shoes, like an Oxford Dress Shoe (Which they almost always should be, if they’re dress shoes!), you should not be able to tie the laces so tightly that the two edges of the shoe meet. I don’t adhere to this advice because some of my clients just have less meat than others on the tops/profile of their feet and when this happens, it’s not a problem. As long as the shoe fits everywhere else, I wouldn’t about this part.


If you have the width and length in check, this shouldn’t be an issue, but just in case: You want a little bit of space between your heel and the shoe, but not too much. My one finger test for sneakers is not applicable here. They should fit a little snugger than tennis shoes do in the heel, but should not be pressing against your heel as to be uncomfortable.

Lace up both shoes and take a short walk in them. There should be little to no slippage in the heel. If there is, they’ll create blisters on your heel and that’s not fun.

Also, since I hear this complaint a lot from guys – If there’s anything like a seam or stitching rubbing against your heel, don’t get those shoes. This is mostly typical in cheaper shoes. This area will never “break in”, so if something is rubbing against your heel when trying them on, it’ll never go away, so stay far away from them unless you like blisters on your heels!

The Best Dress Shoes For Men

See my Men’s Wardrobe Essentials – The Oxford Dress Shoe for my picks.


The Oxford Dress Shoe

This article is part of my Men’s Wardrobe Essentials series.
These are the best mens dress shoes, no questions asked. Anything else pales in comparison. Every man should have at least 2 pairs of Oxford dress shoes in his closet. Not only are they one of the most versatile shoes a gentleman can own – which will work for nearly all formal occasions from business casual to formal – but they’re the de-facto standard shoes to wear with a suit. On top of that, they’ll also work very well with 99% of the items in your Essential Wardrobe. They’re that good.

When you imagine a well-dressed man in a suit, I guarantee he’s wearing a pair of these.

Black & Leather ≠ Oxford Dress Shoes

Don’t think that if a shoe is black and leather, it’s an Oxford dress shoe. I shudder at the thought of those square-toed and/or slip-on monstrosities I see men wearing in place of a proper, lace up, round-toed dress shoe.

Also, if you can see your reflection in your black leather shoes, those are not a proper dress shoe. Those are tuxedo shoes. As the name implies, they should only be worn with a tuxedo. I’ve seen quite a few guys wearing these shoes with jeans. It’s not a good look. Your Oxfords shouldn’t look like mirrors, they should be a little more matte finished. Go to a department store and ask to see their tuxedo shoes so you can see the difference in person.

The image below from RealMenRealStyle highlights exactly what I see a lot of men wearing in place of Oxford dress shoes:


To Cap-Toe or Not?

My opinion about whether you should have a cap toe Oxford or not changes with the wind, so I’ll leave it up to you. There’s not a single scenario when you’d wear a cap-toe over a non-cap toe, so this is entirely up to your preference. 

My clients are split 50/50 on this, too. You won’t go wrong with either, so choose whichever you think looks great and fits your style best.


Should I go for Quality or Value?

For foundational pieces such as these, I’d say go for quality. However, there is a caveat:

How Often Will You Be Wearing Your Oxford Dress Shoes?

  • If you’ll be wearing them more than a handful of times a month, definitely grab a nice, high quality pair. They’ll give you many good years of use and look great the whole time.
  • If you’ll be wearing them once a month or less, go for value. They’ll definitely get the job done and look “good enough”. What’s the use of having a high quality pair of dress shoes sitting in your closet most of the time? I’d take that money and spend it on other pieces you might wear more often](link).

Which Shoes Should I Get?

Since you’ve decided whether you like cap-toe or non cap-toe shoes, now it just comes down to color.

Every guy should have these two pairs of Oxfords in their wardrobe to cover every outfit choice:

  1. A solid black pair
  2. A brown/cognac pair

Anything outside of those two colors will have more specific uses and occasions and definitely falls outside the domain of an Essential Wardrobe item.

The Best Mens Dress Shoes

These are my go-to Oxfords for clients:

Designer Options

Budget-Friendly Options

2 Ways to Wear

For other ways to wear your Oxford dress shoes, check out my Gray Notch Lapel Suit article, Dark Wash JeanSemi-Spread Collar Dress Shirt & Leather Jacket articles.


Model: Tommy Mckeown


Outfit Inspiration


How Should Shoes Fit?

This article is part of my Men’s Clothing Fit Guide.
When I’m fitting my clients in sneakers or casual shoes for the first time, they can easily tell me when shoes are too tight or too loose, but outside of the super obvious, they have a hard time figuring out if they fit properly or not. So I came up with two ways to tell if their shoes fit properly or not. 

the one finger test

Try on the sneakers while wearing a pair of socks you’d normally wear with your sneakers (please, lord, they better not be WHITE SOCKS!) and insert your index finger between your heel and the heel of the shoe.

It should be pretty snug but not so snug that it smashes your finger and is painful. If your finger can’t move without considerable effort, the shoes are too tight and you need to go up a size.

If you can freely move your finger without really touching either your heel or shoe, they’re too big and go down a size.

Squeezing or Pressure on Sides of Feet?


If you feel any squeezing or pressure on either side of your foot, the shoes are too small or narrow. There should be no sensation, good or bad, on any side of your foot if the shoes are fitting properly. If this happens, you should go up a size and see if that helps. If it doesn’t then you may get lucky and the brand makes a wider size, but for sneakers/casual shoes that’s very rare. If they don’t have wide sizes, you’re going to have to find another brand that fits you better.

But Won’t Sneakers Stretch?

I’ve heard this argument a few times from clients. Yes, but it will be very little and will not be enough to go transform them from uncomfortable to comfortable. If you buy sneakers (any shoes, really) thinking that they’ll fit once you’ve “worked them in”, you’re going to have a bad time. Sneakers should fit the second you try them on. If they don’t, they’ll never fit comfortably.

What are the Best Sneakers/Tennis Shoes For Men?

Check out my Men’s Wardrobe Essentials – The White Sneaker story for details about my favorite pairs of sneakers that every man should own.


The White Sneaker

This article is part of my Men’s Wardrobe Essentials series.

White Sneakers AKA Tennis Shoes are like jeans – everyone has them, but not everyone has the right ones or knows what to do with them.

Sneakers look good with any casual outfit (no suits, PLEASE!) and your color choice and how you care for them will have a big impact on whether you’ll look sharp, or just… blah. 

Why White Sneakers?

If you’re reticent about white sneakers, I get it. My clients are a little freaked out by them in the beginning, too. But the reason I prefer white is they look super sharp and literally go with everything you’d wear casually. A pair of white sneakers instantly elevates an outfit to be a little sharper than it would be with other casual shoes. In my book, that’s a good thing.

As a woman, when I see a sharp-looking guy, I want to learn more about him. It’s impressive and intriguing. I’ve been busted for staring a few times because of this :)

If you really, really don’t want to get white shoes, go for a navy color then. They’ll still go with a lot of the other essentials on my list, but not as well as white.

High Tops or Low Tops?

For a foundational piece like this, leave the high tops for later. They’re not appropriate in many occasions where low tops are. High tops are definitely more sporty looking and with pants will bunch up around the ankles and can create a lot of stacking.

Canvas vs. Leather

This is when I’ll leave it up to your preference. Either one will work for the same occasions and outfits. Some people prefer natural fibers over leather. I prefer leather because it doesn’t stain as easily and they’re easier to keep clean, but they’re also (slightly) more costly. It’s entirely up to you. I’ll provide both options below.

Cleanliness is next to Godliness

I’m always shocked to learn that most guys don’t know that women look at 3 things, in this order, when first meeting a man:

  1. Your face/head (duh!)
  2. Your fingernails
  3. Your shoes

Dirty or worn out shoes are a major turn off. Spend 30 seconds and take wet cloth or a Magic Eraser sponge and give your shoes a quick wipe down. A little effort goes a long way and will keep your shoes looking good for much longer.

The Best White Sneakers For Men

Designer Options

Budget-Friendly Options

3 Ways To Wear

*NOTE: You choose the type of lenses (shaded, etc.) during checkout for the sunglasses above.

Outfit Inspiration


Men’s Jeans Fit Guide

This article is part of my Men’s Clothing Fit Guide series.
I see a crap-ton of guys wearing jeans that don’t fit properly. I often wonder who would date or marry these schulbs. The fit guide below applies to you no matter your age or body type, so don’t read this and pull the “Yeah, but I’m not…” routine that some of my clients like to do. It’s a bullshit excuse and this is how your jeans should fit if you’re young, older, short, tall, thin or larger. There’s no excuse for looking like crap in any clothing, even jeans.


how long should jeans be?

A large portion of my clients, when we start working together, think the length of their jeans (AKA their inseam) is something completely different than what it should be. They’re almost always a smaller inseam size than they thought.

Your jeans should be long enough to have a slight/half or full break. It looks much more polished and all around sharper. If you have the perfect pair of jeans, but they’re too long, get them hemmed by a tailor to the proper length. It’s usually no more than a couple of bucks and totally worth it.

The model from my Men’s Wardrobe Essentials: The Dark Wash Jean story has a slight or full break in every image:

I see a lot of guys wearing jeans with stacking like the images below. You want to avoid this at all costs.

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



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. 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 of jeans based on your body type or, if possible, go down a size. As a last resort, you can get a tailor to slim the legs to this size, but it’ll be costly.


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 jeans, the waist will sit a little lower than suit pants, so anywhere from mid to upper hips is where the waist of the jeans should be – definitely nothing below that. The goal is to ensure the waist sits where it doesn’t look droopy in the seat – so pull up those pants!


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, and if that doesn’t work you need get the upper thighs taken in by a tailor to compensate for the extra room in the seat.


You could also start doing some squats and get that area firmed up a bit. I don’t know a single woman that’d complain about that. :)


The Best Dark Wash Jeans For Men

See my Men’s Wardrobe Essentials: The Dark Wash Jeans for my favorite pairs of jeans you should own for your body type.



The Dark Wash Jean

This article is part of my Men’s Wardrobe Essentials series.

Jeans, Denim, Blue Jeans, whatever you call them – the bottom line is that they’re a staple in every man’s wardrobe. But that doesn’t mean most guys know how to choose the right pair.

Every day, I see looks of dissapoinment slapped across people’s faces as the men in their lives waddle around in poopy-pants, flop about in the moo-moo version of jeans or show off their twig and berries.

Let’s fix this.

Every single man, no matter their size, age or body type should have a few pairs of dark washed jeans in their closet. They work for nearly all occasions outside of a formal setting and look good with virtually everything- especially my list of men’s wardrobe essentials. They’ll never steer you wrong and are likely the pants you’ll wear a majority of the time.

The 5 Aspects Of Jeans

1. Wash or Rinse

This dictates how light or dark the jeans are as well as how they’re treated. Light wash = lighter colored. Dark wash = dark.

My preferred wash is dark blue, sometimes called indigo, depending on the brand.

Because of the title of this article, you know I’m recommending that you own dark wash jeans. The reason is because this wash looks great on everybody, hides skinny or thicker legs better than any other color and can be dressed in a casual or less-casual way. I love them so much that I put them on every single one of my clients.

2. Style

This is also called the “cut” and sometimes also called the “fit” of the jeans. Depending on your body type, you should be wearing a certain style. We’ll get into that in a minute, but the most common styles are (in order of slimness):

  • Skinny
  • Slim
  • Straight
  • Boot Cut
  • Relaxed

3. Size

The waist and inseam (leg length) measurements of the jeans. Ex: 32×32 (inches).

If you’ve seen my Fit Guide, you know appropriate jeans sizing, but here’s a quick refersher:

  • They should fit your waist without needing a belt. They can even be slightly tight, as denim will loosen as you wear them.
  • The inseam (length) should leave a slight or full break where they meet your shoes. Anything shorter will look odd and anything longer will bunch at your ankles and throw off your proportions.

4. Denim Type Or Fabric Blend

Denim material can be blended with a variety of other fabrics. Some jeans may have two to three percent spandex and others might have polyester blended into them.

A quick thought if you go with spandex blends:

  • Spandex blends, while a little more comfortable and forgiving in the thighs, tend to stretch out and not retain their shape as well as 100% cotton blends. I’ve definitely seen some “poopy pants” as a result of this.

It’ll depend on what you prefer, I can go either way on this – some of my recc’s below are blends, some are 100% cotton.

5. Fit

I get asked all the time “How should men’s jeans fit?”

Here’s the the trifecta of how your jeans should fit, regardless of age or body type:

  • You should be able to pinch a minimum of 1 inch of fabric, but no more than 1.5 inches on either side of the thigh.
  • They should fit your waist without a belt.
  • They shouldn’t be too short or too long – having a slight or full break. 

Check out my Fit Guide for more in-depth info.

The Best Dark Wash Jeans For Your Build

A quick note about your height: It doesn’t matter. My clients range in size from 5ft 3in to almost 7ft and I’ve never put them in different jeans because of their height. These are the best jeans for short men, tall men, medium-sized men and so on. The only thing that matters is your build: slim/regular or larger.

Slim or Regular Build

You’ll want to get a “Slim” fit. Slim-fit jeans tend to slightly hug the thighs, knees, and calves while tapering down from your knee to ankle.

A lot of my slim & regular built clients initially believe this style will make them look too skinny. This couldn’t be further from the truth. It’s just that they’re used to wearing super baggier clothes to try and hide their slimness, which, coincidentally, just makes them look slimmer. A proper fitting pair of jeans just looks right, regardless of your build, and doesn’t make you look one way or another – I promise.

Things to avoid:

  • Don’t make the mistake of thinking “Skinny” fit is the same as “Slim” fit. “Skinny” fit jeans are usually skin-tight and not appropriate
  • Avoid “Straight Fit” jeans. Like the name implies, the leg of the pants are looser and will be cut straight down from the knee to ankle. This cut will look terrible on you. 
  • If you can pinch more than an 1.5 inches of denim on either side of your thighs, you need to move down to a slimmer cut or get the legs taken in. If you can avoid it, don’t rush to the tailor. Try a size down first or another brand. This is costly for a tailor to do. Having too much fabric on your thighs will make you look smaller, shorter or wider than you are.


I’ve personally worked with and touched each pair of these jeans (in all sections) and they’re awesome. The fit is very accurate, the pocket placement and stitching is great. Diesel runs a little larger in the waist, so go down a size (ex: if you’re a 34 waist, get a 32).

Budget Friendly

I love these because the quality in relation to the price is very good and you can never go wrong with a classic like Levi’s and I love Uniqlo’s wash and they also offer free hemming!

Larger Build

The classic “Straight-Leg” fit is perfect for you. No matter a man’s build, but especially in your case, it’s all about balancing your body’s proportions to make sure your bottom half complements your upper half.

There are a few great brands out there that offer straight-legged jeans with a slightly roomier thigh area which will hopefully solve your frustrations with finding jeans that fit properly.

Things to watch out for:

  • Avoid any cut of jean (all pants in general, for your build) with a taper in the legs. A taper will make you look really top heavy.
  • If you can pinch more than an 1.5 inches of denim on either side of your thighs, you need to move down a size, go to a slimmer cut, try a different brand, or get the legs taken in by a tailor. Don’t get the legs taken in if you can help it, it’s costly for a tailor to do. Having too much fabric on your thighs will make you look wider than you are and completely throw off your proportions.


The wash, quality and fit of these are great and I use them all the time for my larger clients because it makes them look really sharp.

Budget Friendly

Just like I said for the slim to regular built options in this category: I love these because the quality in relation to the price is very good and you can never go wrong with a classic like Levi’s and Uniqlo’s wash is great and they offer free hemming!

3 Ways To Wear


Ashley-Weston-Dark-Wash-Jeans-Look-2-Full Ashley-Weston-Dark-Wash-Jeans-Look-2-Detail

Ashley-Weston-Dark-Wash-Jeans-Look-3-Full Ashley-Weston-Dark-Wash-Jeans-Look-3-Detail-2 Ashley-Weston-Dark-Wash-Jeans-Look-3-Shoes

Outfit Inspiration



Short Pants & Baggy Jackets

This article is part of my Outfit Feedback series.

I love the tailored fit of your clothes, but the length of your sweater and pants are way too short. It looks like you’ve outgrown your clothes!

My Critique

  • Right now, the length of your sweater is making your torso look small compared to the rest of your body. The key with clothing is to make sure everything looks proportional – you want the upper half of your body to look balanced to your lower half. 
  • Your pant’s inseam is way too short and is making everything look “shrunken.”

How To Fix

  • Pull down your sweater so that it hits mid-crotch (about 1.5-2” longer than where it’s currently at).
  • There’s no way to lengthen pants that much. Donate them to charity or pass them onto a friend who’s shorter than you.


The color palette of your outfit – grays, blues, burgundy, browns are great Fall colors that complement each other perfectly. The fit and break of your jeans are spot on! With just one minor adjustment, this outfit would look great. 

My Critique

  • The bagginess of your jacket is disproportionate to the rest of your outfit/body.

How To Fix

  • Definitely size down your jacket to a Medium instead of the large you’re currently wearing. The fit in the body and the shoulders will fit your frame much. much better. 

How Should A Dress Shirt Fit?

This article is part of my Men’s Clothing Fit Guide.
After being asked “How should a suit should fit?“, the next question I get is how should a dress shirt fit. So I put together this dress shirt fit guide for you. My friend Andrew, over at PrimerMagazine put together a great graphic for the proper dress shirt fit below.



The collar should just graze your neck without constricting it when buttoned. If turning your head causes the collar to turn with it, it’s too tight. You should be able to comfortably fit 1 finger inside of your buttoned collar without it choking you. Two fingers is too much (even though the image says otherwise) and looks a little sloppy to me.


The shoulder seam should be right where your shoulder starts sloping down to your arm. Somewhere above the armpit, basically. If the seam starts creeping past where your shoulder slopes down, its too big. If it lands before your shoulder slopes, it’s too small.


Armholes should be comfortable in motion – they should not be so tight that they cut into the underarm. However, they shouldn’t be so loose that there’s a bunch of excess fabric around the armpit. An easy way to check this is to tuck your shirt into your pants – if lifting your arms 45 degrees lifts your shirt out of your pants more than an inch or so, your armholes are probably too low.


They should not be so tight that you can see the details of your arms, but they should also not be so loose as to billow and bunch at the wrist. When you bend your arm, your cuff should not move more than an inch up your wrist. If it does, it’s likely too tight.

The sleeve/cuff should end right at the bend of your wrist.


When speaking of cuffs, there’s two major types: French and Barrel. They should both fit about the same.

With the cuffs buttoned, and your arms at your side, when you bend your wrist so your palms are facing the ground, the sleeves should barely touch the top of your hand (see the video above for details). Ideally, they should be able ¼” above the top of your hand, but if it’s just lightly grazing, that’s OK. Anything more than that and the sleeves need to be hemmed. You want this length so your shirt sleeve slightly peeks out from under your blazer or suit jacket sleeve.

Your cuffs should be tight enough to not restrict movement, but not so loose that your thumb notch at your wrist doesn’t stop the cuff from moving up your hand. It should be a bit looser than a properly fitting watch.





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You shouldn’t be able to pinch more than 2-3” of fabric on either side of the waist. The body of the shirt should fit closely around your torso, no matter what your shape or size. A billowy shirt is no excuse, especially if you’re a larger man.



If you’ll wear the shirt untucked (not really what I’d recommend with a dress shirt) but either way, it should end around the mid-crotch area. Any longer than that and it’s too long and should only be worn tucked in. Shorter than that just doesn’t look good.

Tucked In

If you’ll always be wearing the shirt tucked in, which I recommend for dress shirts, then the longer the better. Traditionally, dress shirts were made very long – usually ending at the bottom or past the crotch. If you have this type of shirt, NEVER, EVER wear the shirt untucked. I can’t tell you how many times I see older guys wearing these types of shirts untucked and I vomit a little inside my mouth whenever I see it. It looks horrible.

My Dress Shirt Recommendations

Check out my Semi-Spread Collar Dress Shirt article for my favorite dress shirts.