How to take risks with your wardrobe

I’ve recently had a number of guys tell me they wish they could be as adventurous with their clothes as I am. First and foremost, I don’t think I take that many risks with my wardrobe. I strive to be elegantly understated, but since I am inspired by a classic style that isn’t too common in Toronto, it stands out. And while I’m glad to hear the desire to take risks is out there, it’s a shame so many men don’t feel the freedom to fully express themselves through their clothes.

That said, I realize – especially in Toronto – that we do not have a culture of elegance, especially in the business world which is the only place in the city you regularly see men in jackets and ties. And while you may see a lot of suits on Bay Street, there is very little joy in dressing well. For most, the suits are uniforms and anything that strays from that uniform is seen as suspect.

However, there are some ways to enjoy your clothes without attracting too much attention. After all, as others have said, you want to be remembered for who you are, not what you wore.

Start at the bottom

I’ve always maintained that a wardrobe is rooted in your shoes. And if you want to begin expanding your wardrobe options, shoes give you an easy starting point. Within the world of classic footwear, there are plenty of looks that remain elegant and refined. That said, I will acknowledge that styles I find sedate and traditional you might find risky. Just the other day I was speaking with a guy who found brown shoes, any brown shoes, a bit too dandy-ish. So I recommended dark brown. He wasn’t sure about broguing, which he felt was too ornate, so I suggested a simple captoe oxford or derby. The key here, however, is quality: buy the absolute best pair you can afford, maybe even more than you can afford. Take care of them and over time you will find their character, personality and style will outshine any potential flamboyance.

Speaking of which, I wouldn’t bother with colourful laces, not until you have really developed your wardrobe and sense of style and they are an expression of that style and not simply an attempt to be different.

Texture instead of colour

One simple way to change things up with your ensemble is to make subtle changes to the textures of your accessories. For instance, instead of the standard shiny dark tie in the office, try a knit tie (pictured above). If that is too much for you – some guys don’t like the square end – grenadine is an excellent compromise. Grenadine ties (blue one pictured below) have a woven texture but the more traditional shape and heft of regular neckties. Plus, Bond wore them. You can also try ties with a matte texture and finish. Some are made of wool or even silk, but when they aren’t shiny, they come across as a bit more relaxed. They also contrast nicely, in a subtle way, with a worsted wool suit.

Monochrome

Sticking to one colour might seem boring but it can actually be a subtle and elegant way to add variety to your wardrobe. This is especially true when it comes to pocket squares. My brother is a lawyer and when he worked at a large firm, pocket squares were met with looks of distrust from other guys in the office (and looks of admiration from some of the women). And while I usually enjoy the contrast a square can provide in an outfit, perhaps understated elegance works better in your workplace. For instance, if you are wearing a dark blue suit with a matte finish, try a silk pocket square in dark solid or patterned blue. You will still have the three-dimensional effect of a square without the added pop of colour. Extend this to your whole outfit – variants on dark blue in your tie and even shirt (stripes or pattern) – and you can be bold without sticking out.

Avoid fun socks

This may seem counter-intuitive: after all, aren’t “fun socks” a socially acceptable way to introduce colour and levity into your outfit? That may be but I see fun socks as a limitation. I want my entire outfit to express my sense of self and I fear that fun socks end up being the only place where risks are taken. As you can see above, that doesn’t mean I limit myself to navy blue. Subtle colours and patterns, I find, are a way to add personality while remaining relatively understated.

Time

The truth is, it takes time to build the confidence needed to take risks. And part of that is the time it takes for others to accept that you not only dress well, but enjoy dressing well. If you stick to it, though, slowly but surely introducing more and more joy into your wardrobe, people will grow accustomed to your sense of style. Eventually, they will be shocked when you show up not in a bow tie and fedora.

[All photos in this article are from my Instagram account]

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