Portrait of a Boss

Toronto’s most eligible bachelor gives us a few essential tips on menswear.

When it comes to menswear, it’s all about looking suave without trying too hard. So instead of consulting an expert in the fashion industry, we decided to turn to one of Toronto’s top bachelors instead – one who always looks impeccable without breaking the bank, and who’s always got a babe dangling off each arm.

To protect his identity (because real bosses don’t do press) we decided to nickname him The Stag for now. And we covered everything from black tie to bumming around, brands to bargains, and boutonnieres to buttons.

Stag: There are two types of suits that a guy in his twenties should have in his closet. There’s a work/evening suit and a casual/trendy suit. Your day job and how dressed up you find yourself in evenings will govern how many of each you have. The work suit should be a more traditional length, likely with two buttons and a good, simple cloth. It should be slim fitting with high arm holes, looks great done up, and have some shirt cuff showing. Because this style is more timeless, I tend to spend more on these suits.

Pony: What about the shirts?

Stag: The shirts should also be slim fitting (you can have a tailor put darts in the back), but when you get them, check that you can still sit comfortably. Take time to make sure the collar is the right size – snug is good. Again, keep the cloth simple and crisp. French cuffs are great, as is collecting cuff links, but if your job has you at a computer all day, keep French cuffs for the evening or your desk will start to chew them apart.

Pony: And shoes?

Stag: I try to have two pairs of black shoes and two pairs of brown. It’s nice to get a more expensive, classic pair in each color that you can baby, and a more trendy pair that you’re happy to kick around in. For the better pair, get rubber put on the bottom as soon as you get them to protect the soles, and buy yourself some cedar shoe trees to keep the leather dry. For the more casual, trendy suit, try some different cloths and colours. I have a few of these and they are shorter in length, more fitted, and look better undone than done up. Because the fit and cloth is more of a look for that season, I try to spend less on them and if they end up in a pile my floor after a big night out, I don’t have to worry about it.

Below: Casual suit.

Pony: What watch brands do you like? And what ones do you find pretentious?

Stag: I don’t really find any watches pretentious unless you’re trying to pull off the white with diamonds rapper style. If you’re going to drop some cash – Bell and Ross, Breitling, Hublot or maybe a Patek Philippe to hand down to the kid you don’t yet have. But for some more affordable options – go with Fossil or Nixon.

Pony: What would you wear on a first date? (Let’s say to Castor for dinner)?

Stag: Castor on a first date? Yikes. Depending on the time of year, some nice dark jeans, a non-work button up shirt, maybe Oxford or whatever, with a casual jacket or a good cardi… or both.

Pony: Does your formal suit change from office to black tie?

Stag: When it comes to black tie, I picked up a Coppley made-to-measure black suit that I had them detail like a tux. I don’t really dig the shiny lapels and patent leather shoes of the black tie look, so I had them make a black, one button suit, with no belt loops, buttons for suspenders, no vents, surgeon cuffs and a peaked lapel. They used a sheen cloth and built it with a canvas backing so it looks formal when it needs to and keeps its shape. I referenced a bad-ass Tom Ford tux when telling the tailor what I was looking for. At the end of the day, it costs less than a decent tux and now I have one that doubles as a beautiful black suit. I wear it with some Boss shoes, a heavy, fitted white formal shirt with french cuffs, some links and a Tom Ford bow tie. Harry’s can hook you up with all the above.

Below: Evening suit.

Pony: Where do you shop for casual wear? And how do you draw the line between being too artsy vs. too boring?

Stag: My favourite stores at the moment are Uncle Otis, Sydney’s, Buckler (which can be touch and go) and if you can afford it: Lileo. I try to keep things pretty clean and classic whatever the trend is. Mixing expensive, quality staples with more affordable, contemporary looks work for me. But at the end of the day, I think the name of the game is wear whatever you want as long as you’re comfortable; if you’re into it, you’ll carry it well and pull it off.

Pony: What’s a trend you’re getting into right now?

Stag: Obviously the heritage brand look is pretty big right now. I have a few things in that vein, but the majority of my stuff is a little more preppy than that. I suppose I have a base of interesting, relatively timeless, well made, clean cut clothes in my closet that I mix with new looks as they come up.

Pony: Jeans. There are thousands of brands, which do you like?

Stag: I like Naked & Famous, Spurr and I have a pair from Buckler that I like. But it’s all about what fits you. Regardless, I’m not a fan of spending loads of cash on them.

Below: Casual wear.

Pony: Jewelry on men. Your thoughts?

Stag: I keep my accessories to sunglasses, watches, pens, socks, pocket squares, and cuff links. I know some dudes that can pull off some good bracelets or necklaces, but it takes a certain look.

Pony: What look do you think is hottest on a girl? With so many options, I know I tend to get lost.

Stag: The hottest look I’ve seen as of late comes from this girl I know, and I’d say her wardrobe falls into a “Chic Boho” category. But at the end of the day, I think versatility is hot. Rocking the cottage look when up north, killing a beach look when on vaca, looking sharp and pro at work, looking sophisticated and sexy for a formal shin-dig … you get the idea.

– Emma Farquharson

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