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

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

The last three years have turned my style upside down. I no longer feel like my wardrobe represents where I am in life and I want to replicate it. To be honest, meI am lost. Where do you even start? – Anders, Toronto

Anders, I’ll let you in on a little secret: Even the most fashionable men among us have at some point found ourselves lost in our style journey.

I found myself in a similar situation to yours a few years ago when I moved to Toronto from Winnipeg. While I’d always thought of myself as dapper, the move revealed significant cracks in my clothing foundation. The rockabilly looks that shaped my wandering years at home suddenly felt alien and uncomfortable in my new surroundings. Uncertainty crept in. Did I have to join the suit and tie brigade I saw on the subway every morning, or worse, give up all color for black? The thought sent a shiver down my spine. Of course I evolved and so did my wardrobe. But how… and without losing me?

For me, the first step came in the form of a philosophical paradigm shift. Until then, I had only equated style with fashion and trends. However, reading the pages of “GQ” made me realize that personal style is so much bigger than fashion and is influenced by so much more. I didn’t have to wear designer clothes—or even know who Issey Miyake was—to have style. I already had it. And that’s unique. You already have style too: all you have to do is edit, tweak and own it based on the interests, hobbies and music tastes that are already authentic to you.

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Psycho babble 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

This is the most important first step for me because it gives a clear picture of who you are and what your style is. Do you have to follow a dress code in any area of ​​your life? How do you commute to work? What are your hobbies? Do you spend most of the year in a warm place? The answers to these questions will help you identify areas to focus on. For example, let’s say you wear tracksuits to work and play golf on the weekends. Make pull-up polo shirts your thing, which look great under a suit and are perfect for golfing.

Choose menswear favorites

It’s incredibly easy to find fashion 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 developed their own style and are great sources of inspiration. When you find someone whose wardrobe appeals to you, pay attention to how their clothes match the outfits you like and what staples they routinely use. When you go shopping, show the staff the inspiration images so they can help you find pieces with a similar aesthetic.

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Think about the fit

Everything comes down to fitting. Especially with the more avant-garde stuff, you’re not sure you can pull this 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 a little research to find yours – a good salesperson at a store you like can help you with that. Two rules of fit I swear by: you never want a piece to look like it has too much material, and never buy “thin” stuff.

Clean up your closet

Granted, this part sucks, but Marie Kondo needs her closet. It is important. If it’s not a tuxedo that still fits, anything that hasn’t been worn in 12 months goes. Also gone is everything that looks sloppy, unusable, dented, way too big or way too small. (When I say gone, I mean cleaned and donated.) If parts are a bit big or a bit tight but in good condition, take them to a tailor and see if they can revive them. You can keep two pieces for sentimental reasons. When that’s done, audit what you have left. There will likely be some gaps that need to be filled.

Invest in a few pieces

By following the steps above, you should now be armed with some knowledge and guidance to create a wardrobe that fits your style and life. All that remains is to spend a little money. I subscribe to buy better, buy less, and feel certain categories are a better investment than others. A good watch, a pair of shoes, a coat, a holdall and, if you’re blind like me, good glasses are worth paying for as they can become your trademarks that you change all the time.

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Buy the advice

The following pieces are playful twists on classic, versatile wardrobe building blocks, all giving you a little touch of spring 2023 without being too flashy.

The loafers

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

GH Bass Loafers, $337, SHOP HERE

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

The jeans

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

RRL jeans, $220, SHOP HERE

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


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

Sport Coat by Canali, $1498, SHOP HERE

You always look well-groomed with a perfectly fitting jacket or blazer. This is crease-resistant, so perfect for on the go, and wind- and water-repellent.

The clock

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

Nomos watch, $1,930, SHOP HERE

A good watch enhances 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 foremost menswear experts and counts Holt Renfrew, Saks Fifth Avenue, Dior and LOUIS XIII Cognac among his clients.


Conversations are opinions of our readers and are subject to the Code of Conduct. Metroland does not share these opinions.

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