Ask The Kit is the real-talk advice column you never knew you needed. Every month, style expert Shayne Stevens 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 ask@thekit.ca
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, I’m 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. The road to great style is paved with “what was I thinking” moments; I’ve made most of the mistakes and have the embarrassing pictures to prove it.
I found myself in a similar predicament to you some 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 colour 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 equated style solely with fashion and trend. You were either in the tribe or you weren’t. 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 style. I already had it. And uniquely so. I just needed to edit it, tweak it and own it, based on the interests, hobbies and musical tastes that were already authentic to me.
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:
1. 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 suiting 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.
2. Pick 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 routinely employs. When you go shopping, show the inspiration images to the associates so they can help you find pieces with a similar aesthetic.
3. Think about fit
Everything comes down to fit. Especially 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 yours—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.
4. Clean up
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 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.
5. Invest
If you follow the above steps, you should now be armed with some knowledge and direction 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, pair of shoes, coat, duffel bag and, if you’re blind like me, a good pair of glasses are worth paying well for as they can become your signature items 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
G.H. Bass loafers, $337, ghbass.com
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.
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The jeans
White jeans are an easy, comfortable style flex any time of year. These ones from RRL are the perfect slim but not skinny fit.
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The blazer
A sports coat or blazer that fits perfectly will always have you looking polished. This one is wrinkle-resistant, so it’s perfect for travelling with, and wind- and water-resistant.
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The watch
A good watch elevates any outfit and this one from German watchmaker Nomos is the ultimate IYKYK move.
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