A men’s fashion expert on how to inject style into a wardrobe
7 mins read

A men’s fashion expert on how to inject style into a wardrobe

A men’s fashion expert on how to inject style into a wardrobe

Ask The Kit is the real-talk advice column you never knew you needed. Every month, style expert Shayne Stephens answers your pressing men’s style questions. What are the best men’s shirts? What kind of suit should I buy if I’ll only have one? Send your Qs to [email protected]

The past three years threw my style for a loop. I no longer feel that my wardrobe represents where I’m at in life, and I want to rebuild it. To be honest, Im lost. Where does one even begin? —Anders, Toronto

Anders, I’m going to let you in on a little secret: even the most fashionable men among us have felt lost at some point on their style journey.

I found myself in a similar predicament to you a few years ago when I moved to Toronto from Winnipeg. While I’d always fancied myself dapper, the move exposed significant cracks in my sartorial foundation. The rockabilly looks that had defined my rambling years back home suddenly felt foreign and uncomfortable in my new surroundings. Insecurity crept in. Was I going to have to join the suit and tie brigade I saw on the subway every morning, or even worse, abandon all color for black? The thought sent a shudder down my spine. To be sure, I was evolving and my wardrobe needed to as well. But how… and without losing myself in the process?

The first step for me came in the form of a philosophical paradigm shift. Up until then, I had equalized style solely with fashion and trend. By reading the pages of “GQ,” however, I realized that personal style is so much bigger than fashion, informed by so much more. I didn’t need to wear designer clothes — or even know who Issey Miyake was — to have a style. I already had it. And uniquely so. You already have a style, too: You just need to edit it, tweak it and own it, based on the interests, hobbies and musical tastes that are already authentic to you.

Psychobabble aside, there are some simple, practical strategies that will help get your wardrobe moving in the right direction. Here are the five things I recommend you do:

Assess your lifestyle

To me, this is the most important first step, because it provides a clear picture of who you are and what your style is. Are you required to follow a dress code in any area of ​​your life? How do you commute to work? What are your hobbies? Do you spend a significant part of the year somewhere warm? The answers to these questions will help you identify areas to focus on. For example, let’s say you wear casual suits to work and play golf on the weekends. Make elevated polo shirts, which look great under a suit and are perfect for golf, your thing.

Pick men’s fashion favourites

It is incredibly easy to find sartorial inspiration on social media, no matter your area of ​​interest. Use it! A list of people to follow to get you started: Nick Wooster (@nickwooster), Satoshi Kawamoto (@Satie_San), Nicco Cesari (@niccocesari), Matthew Zorpas (@matthewzorpas), Momo (@boon.vivant_) and Tomoyoshi Takada ( @tomoyoshi_takada) — these are all guys who have established their own signature style and are great sources of inspiration. When you find someone whose wardrobe resonates with you, take note of how their clothes fit in the outfits you like and which staple pieces he regularly employs. When you go shopping, show the inspiration images to the associates so they can help you find pieces with a similar aesthetic.

Think about fit

Everything comes down to fit. Especially with the more avant-garde stuff you’re not sure you can pull off — if it fits well, that’s the difference between looking good and looking completely out of place. Certain cuts and proportions work well with certain body types, so your homework is to do some research to figure out yourself — a good sales associate at a store you like can help you with this. Two fit rules I swear by: You never want an item to look like it has too much material, and never buy “skinny” anything.

Clean up your closet

Admittedly, this part sucks, but you need to Marie Kondo your closet. It’s essential. Unless it’s a tuxedo that still fits, anything that hasn’t been worn in 12 months goes. Also gone is anything that looks sloppy, beat-up beyond saving, way too big or way too small. (When I say gone, I mean cleaned and donated.) If the pieces are a tad big or a tad tight but in good shape, bring them to a tailor and see if they can revive them. You’re allowed to keep two pieces for sentimental reasons. When that’s done, audit what you have left. There will likely be some gaps that need filling.

Invest in a few pieces

If you followed the steps above, you should now be armed with some knowledge and directions for developing a wardrobe that suits your style and life. The only thing left is to spend a little money. I subscribe to buy better, buy less, and feel that certain categories are a better investment than others. A good watch, a pair of shoes, a coat, a duffel bag and, if you’re blind like me, a good pair of glasses are well worth paying for as they can become your signature item that you wear on constant rotation.

Shop the advice

The pieces below are playful twists on classic, versatile wardrobe building blocks, all of which will give you a little spring 2023 swagger without being too out there.

The loafers

The building blocks of a more stylish men's wardrobe include classics with a twist.

GH Bass loafers, $337, ghbass.com. SHOP HERE

Perfect with denim, shorts or a suit, the penny loafer is a must-have in your footwear rotation. The white contrast panel ups the style quotient here.

The jeans

The building blocks of a more stylish men's wardrobe include classics with a twist.

RRL jeans, $220, ssense.com. SHOP HERE

White jeans are easy, comfortable style flex any time of year. These ones from RRL are the perfect slim but not skinny fit.

The blazers

The building blocks of a more stylish men's wardrobe include classics with a twist.

Canali sports coat, $1498, harryrosen.com. SHOP HERE

A sports coat or blazer that fits perfectly will always have you looking polished. This one is wrinkle-resistant, so it’s perfect for traveling with, and wind- and water-resistant.

The watch

The building blocks of a more stylish men's wardrobe include classics with a twist.

Nomos watch, $1,930, nomos-glashuette.com. SHOP HERE

A good watch elevates any outfit and this one from German watchmaker Nomos is the ultimate IYKYK move.

Toronto-based writer and luxury consultant Shayne Stephens is one of Canada’s leading men’s fashion experts, counting Holt Renfrew, Saks Fifth Avenue, Dior and LOUIS XIII Cognac among his clients.


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