The #AskAW Show: Episode 07

In this episode I answer:

Q: How to wear boat shoes?

A: Pair them with Dark Wash Jeans, Chinos, a nice belt, and either a Polo Shirt or Oxford Button Down Dress Shirt.

Q: Looking to buy a peacoat online, how do I ensure it fits properly over a suit or blazer?

A: First, you should never wear a peacoat over a suit or blazer. Second, buy your normal size plus the next size up and return the one that doesn’t fit the best.

Nathan sent an update about asking out his 10 year long crush.

Watch the video for an update about Nathan asking out a 10 year long crush from Episode 4.

 

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

How Should A Polo Shirt Fit?

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

Collar & Neck Opening

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

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

Ashley Weston Long Polo Shirt Buttons

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

Polo Shirt unbuttoned bad Ashley Weston

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

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

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

Sleeves

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

Sleeves Polo Shirt Ashley Weston

Body/Torso

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

Length

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

Crotch Measurements

Tails

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

Best Polo Shirts For Men

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

The Polo Shirt

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

A good polo shirt will:

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

Fabric

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

Piqué Cotton

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

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

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

Pique Cotton Vs Cotton or Silk Blended Polos Ashley Weston

Cotton & Cotton Blended Polos

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

SilkBLendPolo - Ashley Weston

Colors, Patterns, Piping, Etc.

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

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

To Tuck or Not To Tuck

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

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

Leggo my Logo

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

How Should A Polo Shirt Fit?

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

The Best Polo Shirts for Men

Designer Options

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

John Varvatos Hampton Polo 

Sunspel Charcoal Jersey Polo Shirt

Ermenegildo Zegna Mercerized Cotton Polo Shirt 

Burberry Navy Silk Cotton Polo

Theory Black Boyd Polo

Budget-Friendly Options

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

H&M Polo Shirt 

Uniqlo Navy Dry Pique Short Sleeve Polo Shirt

J.Crew Black Pique Cotton Polo

3 Ways to Wear a Polo Shirt

(Sunglass lenses sold separately)

H&M Polo Shirt

J.Crew Broken-In Chino in 484 Fit

Vans Authentic Sneakers

True Vintage Revival Glasses 

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

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

Philipp Plein Coat So Cool

Ermenegildo Zegna Mercerized Cotton Polo Shirt

Brooks Brothers Slim Fit Dark Khaki Garment-Dyed Chinos

Nike Tennis Classic Sneakers

Allen Edmonds Black Poplar Belt

IWC Portugieser Automatic Watch

John Varvatos Lafayette Sunglasses

 

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

Burberry Modern Fit Wool Part Canvas Jacket 

Burberry Silk Cotton Polo Shirt 

Levis Chino 511 Slim Fit Jeans 

Salvatore Ferragamo Penny Loafer Shoe

Allen Edmonds Brown Poplar Dress Belt

Piaget Altiplano Watch

John Varvatos Lafayette Sunglasses

Outfit Inspiration

 

The #AskAW Show: Episode 02

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

Show Notes & Links

Q: I’d like to find a good pair of suede Chukka Boots, but I’ve got big feet – Size 15, can you help?

Allen Edmonds - Dundee Suede

Allen Edmonds – Dundee Suede

 

Q: What can I wear with my blue suede wingtips?

Dark wash jeans 

 

Q: How can I dress nicely in really warm weather?

Polo Shirts

 

Linen Button Up Shirt

 

Chino Pant

 

Shoes

 

Q: What watches would you recommend for a guy with skinny wrists who wants a brown band?

 

Q: What do you think about the proportions of this jacket?

Fashionbeans.com story I commented on. 

 

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