Street Style: The Gentlemen of Toronto

June 3rd, 2014

After the “Gentlemen’s Evening” we hosted in Toronto, Alex and I stuck around the city for a few days to put together profiles on some of the major players in the menswear scene and shoot some Street Style around town.

Here’s some of the stylish gents we found cruising the streets.

1. Tailored in Taupe

Lots of great action happening here. Awesome taupe color, well-scaled pattern mixing, slim not skinny fit, sharp grooming, flattering eyewear shape… Well played, player.

2. A Taste of Japan Style

This is Japanese street style in its purest form. A mix of funky streetwear, bold colorful patterns, simple old-school tailoring, and worn-in Americana. All put together with a quirky “it’s better if it’s not over-thought and a little imperfect” attitude… Shout-out for that “North America” hybrid tote, too.

3. Pinstripes & Paisleys

Some 80’s Ralph Lauren inspiration here with the bold Wall Street stripes, the double paisley action, and the low-rider kiltie loafs. Don’t match your tie and pocket square – compliment them!

Extra points for the on-color-palette Toronto Blue Jays pin, of course.

4. Suit & Sneakers

Lance is an editor at Sharp Magazine who really knows his way around a suit with sneakers. At the party he rocked a mean navy DB corduroy and here he’s going with a casual cotton – with the same sneakers.

5. Smart & Simple

Two things made this simple casual look for me: the design of the shades and the sleeve creases on that sharp bomber.

6. Some Thing Never Get Old

Alex snuck this shot from the back of a cab at a red light. Just a young buck doing the classic “business casual prep” look with style: navy blazer with gold buttons, contrast cutaway collar, slim khakis, brown lace-ups. I like the slim document case too…but in a beat-up brown this would have been next level.

7. Brand Ambassador Chic

The infamous “TO” in TO, rocking a terry cloth rugby shirt with the shrunken leather backpack from my collection with Frank Clegg. Thanks for the continued support, brother.

8. Summertime Separates 

Nothing says “it’s finally warm out” like a seersucker jacket, faded yellow chinos and sockless cognac monkstraps…. How about the pulling together of the yellows and the consistency of those leathers! We should have taken a close-up too…the shirt is a very subtle linen polka dot chambray.

9. A Taste of Italy 

My new friend Neil Watson and I are going to work together on something creative. Not sure what yet, but he’s on my “to connect and build with” list. The guy has some very smooth Italian-inspired style as well… Feature coming soon.

10. Monsieur on the Move

En route in another seersucker jacket. Making it look easy and breezy.

11. The Man Who Started It All

Ryan Oozeer is my best friend and brother from another mother. He taught me what it meant to be “fresh” at a young age. I used to wear his clothes at least three days a week in high school, because he always had the flyest shit! We’re grown up now but the swag never wears off.

12. Monochrome Monday

Another great example of the power of simplicity and monochromatic palettes. You don’t need bold pieces, just a good eye for color, and accessories. Extra points for the linen knit, the retro glasses and the use of the belt strap…the tattoos give him an interesting edge as well… Anyone know this gentleman?



Thanks, as always, for reading.

Yours in style,

Articles of Style


Photography by Alex Crawford