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To many men, tailoring is something to wheel out for weddings, funerals and little else in between, with most offices operating a dress-down policy all week round. When sneakers and a solid sweatshirt will do pretty much everywhere, why bother with a stiff, somber two-piece? But as of late the stylish set have been showing us that suits needn’t be so serious, especially when loosened up and mixed in with a little streetwear steez...
street styler in tailoring and streetwear

Supersize me

A common argument against tailoring is that it can be restrictive and uncomfortable. But if you forget about skinny fits and go for something a little more relaxed, as this gent has done, then that’s not the case at all. The key is to think slouchy rather than baggy — you don’t want to look like you’ve been raiding your dad’s wardrobe. Balance wide-leg pants out with bulky retro sneakers and perhaps add a pair of tiny shades for some '90s-style proportional playfulness.

street styler in tailoring and streetwear

Chairman of the board

This fella has taken the opposite approach by keeping his suit slim and cropped, and instead freshened up his classic waistcoat-and-pant combo with a psychedelic tee, fresh Vans and a bright red beanie. As a result, he looks like the skater son who just inherited dad’s firm (Richie Rich reboot, anyone?). First order of business: leather trenches for all.
street styler in tailoring and streetwear

Big blue

Not a fan of muted tones? Then go ahead and slap some color on, as this guy has done. There’s nothing dull about his bright blue DB (that’s double breasted to you and I), especially given the slight mismatch between his jacket and pants. The oversized fit, graphic tee and bag slung over one shoulder are taking us straight back to our school days — if only our uniform was remotely as slick.
street styler in tailoring and streetwear

Mr. Steal Your Sleeves

For as long as we can remember, you had two choices when it came to a jacket: single or double breasted. But over the past year or so, a third way has emerged — taking the simplicity of the former and the wrap-around cut of the latter. It’s been dubbed the one-and-a-half breasted, which sounds like pointless fashion talk, but as this guy has shown it’s completely legit. He’s taken things one step further by going short sleeved and sans shirt, making this feel more like a souped-up Cuban shirt.
street styler in tailoring and streetwear

Pictures: IMAXtree

Rainy-day hero

A cagoule, checked blazer and side-stripe track pants. It sounds like the last few items on a sale rack, but somehow this dude pulls it off. Maybe it’s the subtle color matching between his jacket lining and his sneakers, or maybe it’s because everything has a slight '80s feel — big chain included. Who are we to question? It just works.