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 White Sneaker

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. 

Have questions? Curious what others think?

Join us in the comments section of the video above.

 

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. I personally love using Jason Markk’s cleaning kit – check out my video about How To Clean Dirty Sneakers. 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

$495 – Givenchy Urban Street Leather Sneaker – all white (for white with a touch of blue on the heel, get these)
$495 – Saint Laurent SL/01 leather sneakers
$370 – Acne Studios Adrian leather sneakers
$410 – Common Projects Original Achilles leather sneakers

Budget-Friendly Options

$65 – Converse Jack Purcell Canvas Sneaker (leather option buy here)
$55 – Vans Old Skool Sneakers – in True White
$60 – Adidas Stan Smith Sneakers

3 Ways To Wear

$200 – Topman Khaki Suede Bomber Jacket (the burgundy is no longer available, but I love this green suede version)
$10 – H&M Crew-neck T-shirt in black
$165 – J. Brand Tyler Taper Fit in slate resin (Love that the color, stitching, and hardware are similar color)
$65 – Converse Jack Purcell Canvas Sneaker (leather option buy here)

$13 – H&M Polo Shirt Slim Fit in black (**THESE ARE THE BEST POLO SHIRTS!!!!)
$40 – Uniqlo Slim Fit Chino Pants in navy (Fit is awesome and they’ll hem your pants for free)
$55 – Vans Old Skool Sneakers – in True White

Burberry London  Slim Fit Travel Tailoring Wool Jacket
$78 – J.Crew Cotton Cashmere Slim Fit Cardigan in heather charcoal
$69 – Brooks Brothers Non-Iron Milano Fit Button-Down Collared Dress Shirt
$170 – Diesel Buster 0607A Tapered Jeans (I’ve bought my fiance 3 pairs of these – they’re that good!)
$73 – Brooks Brothers Leather Formal/Casual Belt in brown
$65 – Converse Jack Purcell Canvas Sneaker (leather option buy here)

White Sneaker Outfit Inspiration/How To Wear White Sneakers

The Dark Wash Jean

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.

Have questions? Curious what others think?

Join us in the comments section of the video above.

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.

Designer

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).

Tom Ford Slim-Fit Stretch Indigo Denim Jeans
RRL Slim Fit Selvedge Jeans
JBrand Tyler Taper Fit in Rasalas
JBrand Taper Tyler Fit in Blue Hood
Diesel Buster Jeans

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!

Uniqlo Stretch Selvedge Slim Fit Jeans
Levi’s 511 Slim Fit Stretch Jeans

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.

Designer

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.

AG Graduate Jeans
JBrand Kane Jeans 

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!

Levi’s 514 Tumbled Rigid Jeans
Uniqlo Selvedge Straight Leg Jeans
Gap 1969 Straight Fit Jeans

3 Ways To Wear

Ashley-Weston-Dark-Wash-Jeans-Look-1-Full

Levis Sunset Pocket Tee
JBrand Tyler Taper Fit in Rasalas
Allen Edmonds Wide Basic Belt
Vans Authentic Sneakers

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

Brooks Brothers Suede Barracuda Jacket
J. Crew Garment-Dyed Henley
JBrand Tyler Taper Fit in Rasalas
Allen Edmonds Wide Basic Belt
Vans Authentic Sneakers

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

Modern Fit Travel Tailoring Virgin Wool Suit
Brooks Brothers Red Fleece Spread Collar Sports Shirt
JBrand Tyler Taper Fit in Rasalas
The Tie Bar Knitted Tie
The Tie Bar Cotton Pocket Square dark Charcoal Tipping
Johnston & Murphy Fielden Cap-Toe Dress Shoe
IWC Portuguese Automatic Watch

Outfit Inspiration