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

  • Joe

    Ryan Oozeer hits my style bang on. The story also appeals to me as it reminds me of how I was influenced by my older brother went I was younger.

  • Gazman

    Bloke in #8 looks great. As the Big L would say, the preppy tie pulls the whole look together. I also reckon this is exhibit A on why a single strap monk is so much more elegant than the ubiquitous double monks seen on every iGent.

  • DJ

    Wow, I finally put two and two together! I didn’t realize I knew the infamous TO. Looking good man.

    • TO

      Thanks DJ!

  • Jeanscuffed

    Screw it, they ALL make me go like that, especially Mr. Monochromatic (looking like Macklemore’s mentor)

  • StyleSubjectivism

    #3- affectatious at its finest.

  • Miguel

    I was away a couple of day but a lot of great outfits in TO, specially #1 #8 #10…on point.

  • PositiveJostle
  • khordkutta

    #1: Polka Dots in the T. Dot.
    #2: Just by the attire, i wanna hang out that guy.
    Really dig the of #8 and #12

  • Jeff McAllister

    This series of Street Style looks resonated with me more than most. Maybe it’s that things seem a bit less forced north of New York, or maybe it’s just my Canadian state of mind. Either way, way to represent Toronto!

    Next stop, a swim through the sea of yoga pants to find “Vancouver’s Modern Gentlemen?”

  • John B

    #3 looks really busy and something looks off with the shoes on #6.
    Also, TO’s collar is huge, which kind of ruins the look for me. Liked almost everything else though! Suitsupply could use #9 as an advertisement (the jacket and pants are probably from them, I’m not saying he copied the look)!

    • TO

      Hey John B! Understood the super wide collar isn’t going to be everyone’s bag haha

      I’m not even a big fan in general of the oversized proportions of the ’70s (though they are starting to grow on me).

      I spotted the piece in a vintage shop in Austin, TX and the wide collar really struck me as unique (because we have all seen a rugby with a typical collar before) and I actually liked the collegiate-straight-from-the-70 vibe it has, without making you go full John Travolta.

      • Juan

        I actually LOVE that collar, TO! It’s an unexpected way to mix things up a little bit. Also loving those suede chelseas, it’s overall an awesome clean look!

        • TO

          Thanks brother;)

    • LC

      Agree on #3. Even just changing the striped socks to a solid would go a long way towards toning things down a bit.

  • MS

    That first suit is a goddamn work of art. Great photos, guys. Alex’s eye really shines in this set.

    • LC

      Agree strongly on both counts.

    • Alex Crawford

      Thanks MS

  • WideEyesTWBlog

    Man, Toronto has style! What really got me, though, was the fact that I want ALL of the shoes. All of them.

    • dani

      NY has more

      • WideEyesTWBlog

        More…style? I don’t think anyone (at least not myself) was making any sort of argument against that.

        NY is certainly more of a fashion epicenter, which is exactly why I was impressed with the sartorial skill coming out of Toronto. I live in Chicago, and rarely see people step it up to this level.

  • TheWolvesden

    12 is class. I would love to channel that type of palette the most

  • Juan

    The length of the jackets in looks #1 and #8 really kill the whole thing (#8 especially is awesomely put-together, with a properly-long it would’ve been sublime), too bad.

    But otherwise I’m pleasantly surprised by these gentlemen and the overall style consciousness in Toronto! Awesome pieces all over the place, I just can’t get over that linen knit from the last look!

    One of the best Street Style posts I can remember, thanks TSB!

  • cam

    Are we voting? Cause I gotta go with Neil on that Cucinelli vibe

  • Shawn

    #1 nice overall look but I’d wear another tie, #3 excellent tie, very bold! #9 excellent in everyway, #10 I love it but I’d rock other shoes. Some stylish folks in Toronto!

  • Christopher

    Man, too bad I was extremely ill over the past few days! Would’ve loved to be a part of this photo shoot. Hopefully TSBMen come back to TO this summer!