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Fashion & Style

10 styles that define men's street fashion in Toronto

Posted by Staff / June 25, 2014

street style torontoMen's street style in Toronto is in constant flux as the city's fashion community and menswear retail scene continue to expand. With a growing Fashion Week that features strong showings from local menswear designers (including Klaxon Howl, Sid Neigum, and Christopher Bates) and a burgeoning reputation as a harbour for thread-wealthy boutiques, Toronto's gents are drawing from local resources to establish their own fashion go-tos.

Here are 10 styles that define men's street fashion in Toronto.

Dapper gentleman (top)
Otherwise known as "mad style" (à la Don Draper), these gents dress head-to-toe in timeless silhouettes and tailored staple pieces. Slim, deep blue suits are topped off with skinny ties and freshly shined shoes. They know how to keep their whites crisp, what to do to maintain the perfect cuff on a dark-wash denim, how to fold a pocket square, and just how fitted a fitted jacket should be.

street style torontoClean-cut hip-hop
Think back to deep-style hip-hop of the 90s - patterned bomber jackets, tracksuits, chinos, camouflage. Set against a modern backdrop of minimalist, skater, and boyish hipster influences, these types prefer a more tailored look, opting for an easy-going, put together, and ultimately fresh approach.

fashion styles torontoModern rockabilly
The term "rockabilly" comes from the combined genres of rock'n'roll and "hillbilly music" - who'd have known, right? These Torontonians are clad in leather jackets, fitted, cuffed trousers, white T-shirts, slicked-back, undercut hair, and worn-in attire. In the 21st century, Modern Rockabilly is the badass version of comfortable, the retro variety of vintage, all-encompassed by the cool attitude of streetwear.

street style torontoNew-school funk
You'll always notice this look when it walks - or rather, struts - into a room. It's a style with undeniable 70s influences (see: Earth, Wind & Fire, Al Green), clean-cut vintage finds, thrown in with a warmth and rich personal flair that says "oh hey, girl" (though it has far too much class for a line like that).

street style torontoEdgy avant-garde
Avant-garde is the conversation starter of styles. It's not often that you find someone who plays well with interesting silhouettes, open androgyny, and experimental fashions. Although the avant-garde guy typically dons all black attire, it's this blank canvas that makes their ultramodern aesthetics and thought-provoking use of clothing stand out all the more.

street style torontoBoho skater boy
A regular of Bonnaroo (going to Burning Man next year, bro), beach bonfires, and the occasional art school soirée, he's the teen-at-heart giving a nod to adulthood via buttoned-to-the-neck, short-sleeved tropical-printed shirts and khakis. On most days, though, his wardrobe consists of modern skatewear: ironic t-shirts or brand-heavy tank tops, beat-up sneakers, holey jeans, and five-sided caps. Oh, and Urban Outfitters. So much Urban Outfitters.

street style torontoBay St. casual
They just barely border on too cool for the Financial District, repping a sensibility that's entrepreneurial and fresh. They're a business-savvy private school boy grown up and wrapped in red trousers, slim-fit shirts, pea coats, and the like, toting the latest issue of GQ. He's an old-fashioned drinker who's nowhere near old-fashioned; a condo-price talkin', jet-settin' alpha male.

street style torontoNew-age minimalist
A minimalist's closet must look much like that of Homer Simpson's pared-down wardrobe: a selection of single-shade pants, shirts of the same size and shape, and an infinite collection of repeat shoe styles. Those bare-bones aesthetics are expressed in black and white monochrome ensembles, served with a side dish of a "use less" mentality. They're sensible and practical. This is the Alexander Wang generation - get used to it.

street style torontoBoyish chic
Boyish chic is where clean-cut and polished preppy meets a hint of feminine prints and colours: Orange bermuda shorts and a teal polo shirt? Yes, please. Paisley paired with stripes? In perfect moderation. Often shy with a hint of sass. Never underdressed.

street style torontoPop art eclectic
Not all personal styles are representative of a single genre or look - eclectics borrow pieces from different genres, mix high and low, and reference a variety of cultures and time periods, all of which ultimately create a look that's all their own. Key looks to the pop art eclectic include bright colours, fun silhouettes, playful accessories, and super fun pop culture references.

Writing by Alex Brown. Street style photos by Mauricio Calero.



Bite Mark / June 25, 2014 at 01:32 pm
Let the roast begin
mike in parkdale / June 25, 2014 at 01:46 pm
something something hipsters something....
.. replying to a comment from Bite Mark / June 25, 2014 at 01:49 pm
And deservedly so.
trickydisco / June 25, 2014 at 01:57 pm
pop art eclectic?? that's the stupidest shit i've ever seen
go figure. / June 25, 2014 at 02:01 pm
Somehow Clean Cut Hip Hop is actually the best of the lot.

Never thought i would say that.
d / June 25, 2014 at 02:05 pm
tis to laugh
Jonathan / June 25, 2014 at 02:09 pm
Bahahahahahahahahaha *takes breath* hahahahahahaha!
iliveattheverve / June 25, 2014 at 02:09 pm
you forgot the ubiquitous forever-frat-guy cargo-wearing 30-40-50-60-year-old man-child too old to be wearing A&F
Kate / June 25, 2014 at 02:12 pm
apparently buying clothes about 2 sizes too small is a thing. Nice to see "Bay Street Casual" hasn't changed in about 30 years; used to be called preppy...
Nash / June 25, 2014 at 02:19 pm
Trying way too hard...
Katherine / June 25, 2014 at 02:21 pm
Great round-up. Love seeing people express themselves through what they wear. Who am I to judge someone else's personal style? Except when they wear those 'Been Trill' shirts. Thank you for not showcasing those.
Jeremy / June 25, 2014 at 02:22 pm
I don't think they're ALL bad, but some are a little odd to be wearing outside the house during the day-time. I've always been intrigued by people who dress in the "Edgy-Avant-Garde" look. You see it a lot with this new wave of popular rap artists like A$AP Rocky and I guess they want to call it high-fashion but I just don't think it's very functional.

To each their own. I've got no problem with any of them...
RD / June 25, 2014 at 02:24 pm
You must have REALLY been scraping the bottom of the barrel when you were looking for a topic to write about. Seriously.
Wtf? / June 25, 2014 at 02:26 pm
Is that Blake Griffin wearing a dress?
D Money replying to a comment from RD / June 25, 2014 at 02:41 pm
Next article: 6 kinds of hats I saw today
Joseph / June 25, 2014 at 02:49 pm
I like all of them
Kid Cornish / June 25, 2014 at 02:49 pm
"The term "rockabilly" comes from the combined genres of rock'n'roll and "hillbilly music" - who'd have known, right?"

Well, d'uh.
Ian Mac / June 25, 2014 at 02:56 pm
LMAO. This makes Toronto look like a city of douche bags when actually it's awesome. Great job Blog TO!
whattheheck / June 25, 2014 at 03:02 pm
so sad...
akswun replying to a comment from Ian Mac / June 25, 2014 at 03:13 pm
Where's the douche?
Closest thing is the 'Bay St. Casual' but thats even far fetched.
If the article was on the only style from King St. West then you would be right. But guess what.... you're wrong!

Good article blogTO. Can't wait for the Female follow up.
Steph / June 25, 2014 at 03:17 pm
More like 50 shades of hipster...
Bob / June 25, 2014 at 03:19 pm
Are you sure that "edgy" guy isn't just in fact homeless?
Nev / June 25, 2014 at 03:33 pm
I may not like all the different styles you've displayed here but I appreciate the time and care these guys have taken.

And Mr New-School Funk? Smokin'!
Ian Mac replying to a comment from akswun / June 25, 2014 at 03:43 pm
I think you're taking the term douche-bag as something quite literal (I know the sort of person you're talking about). Maybe I should say a city full of fools instead. These guys all just look different degrees of ridiculous to me, bar one or two.
Crash replying to a comment from go figure. / June 25, 2014 at 03:58 pm
Confused / June 25, 2014 at 04:04 pm
Is it just mean or are men starting to look very feminine? While I can appreciate the fashion, it seems to me they could use a burger.
Fashionista replying to a comment from Nash / June 25, 2014 at 04:08 pm
Better than not trying at all, Mr. Gortex.
JustAnAvgGuy / June 25, 2014 at 04:18 pm
Why do people try SO HARD to look/be different?
I see. replying to a comment from Crash / June 25, 2014 at 04:24 pm
Thats the point exactly.

The rest look like someone with ADHD was playing with a Mr Potato Head.
The Baron replying to a comment from Confused / June 25, 2014 at 04:27 pm
I saw 9 hipster males, and 1 man (#2) sorta, dude's got tooth pick legs. Seriously were the hell did they come up with these titles and comparison. #1 looks NOTHING like the "Dapper Gentlmen" you see in Mad men. Hell their own description doesn't even match the picture. And the rest well....REAL men can't fit into skinny anything. Our calves and quads are too big from squatting ass to grass heavy fucking weight.
Buckner / June 25, 2014 at 04:28 pm
You know pants are allowed to make it all the way down to your shoes, right?
Kate / June 25, 2014 at 04:29 pm
These guys are (I'm pretty sure) models, not just dudes on the street. They've been "over-styled".
The Peon replying to a comment from The Baron / June 25, 2014 at 04:35 pm
Meh...there's no such thing as "REAL" or fake men. We're all just people. Lame, too predictable criticism.
The Peon replying to a comment from The Peon / June 25, 2014 at 04:54 pm
Of course there are REAL men out there. Every VC and Medal of Honor recipient, Theodore Roosevelt, Arnold, Gen James Mattis USMC Ret'd, Lumberjacks, Crab Fishermen, Jim Wendler, Doug Young, Anatoly Pisarenko, I can keep going all night.
kevinn / June 25, 2014 at 05:53 pm
Two things..

1. How come I never see these guys around (minus the 'hip hop' and 'boho skater' ones)?
2. How many of them work in retail?
Kingpin / June 25, 2014 at 06:24 pm
Okay, so basically you have two looks here, one for gents and one for bros. Most Toronto men's style seems derived from what they thought was cool when they were 14; they stick to dressing like boys not ready for the responsibility of being a grownup. Bros are easy to spot because they sport the same looks as 8 to 12 year-olds in your local playground. The gents are embracing and owning their lives and are striving to demonstrate this with their style of dress; bow ties, laced shoes, cufflinks, and so on. Let's encourage more Toronto men to task the leap and associated risk in becoming gents!
gz / June 25, 2014 at 06:45 pm
definitely missed normcore
linden / June 25, 2014 at 07:17 pm
Edgy avant-garde -is this the politically correct term for man in skirt
Jalen / June 25, 2014 at 07:46 pm
I find if hilarious that half of these men on here wanna criticize people for being different lol. I'm actually guy number 8 & to be honest everyone has their opinion so I can't blame anyone or get upset but Toronto is focused on being apart of the norm that they don't wanna try new things, half of the people in Toronto dress BASIC. You guys have no sort of style what's so ever, it's the same damn thing every where you go. You guys wanna criticize but you all need to look up what fashion really because everyone in London where's this shit. Loll reasons why I don't belong here. Everyone is so focused on dressing to how society wants them dress & are afraid of what people think, all of these men look acceptionally great. Some more than others but they all have a sense of style & was brave enough to showcase it so at least give them credit, I'm pretty sure some of you that commented don't even have a sense a style lol, I would love to see you put a picture of your outfit on a blog & we'll see how you do sounds good? Lol. Anyways I appreciate everyone's honesty on here but if you guys need tips follow my Instagram: _lickmyfashion_ good day everyone :)
shubjero / June 25, 2014 at 08:02 pm
So many ideas for Halloween 2014. Thanks blogto!
snickers replying to a comment from shubjero / June 25, 2014 at 08:56 pm
@shubjero: so funny! hahahahahaha tee hee
Guy / June 25, 2014 at 09:01 pm
I like how any attempt to not wear a graphic tee or tuck your polo into your dad jeans is equatable to being a hipster. Please just go back to calling people assholes, k?
Alex / June 25, 2014 at 09:05 pm
It's June 25. What are these some of these guys doing in sweatervests, turtlenecks, and leather pants (!?). They must be boiling.

That being said I dig some other these styles more than others. ("avant-garde? more like avant-garde your children against this homeless creepo.")
Indy / June 25, 2014 at 09:40 pm
These are awesome. It's great to see acknowledgement across genders of fashion forward thinking! Especially fashion that breaks molds. Plus these outfits are super neat. I love seeing the bold looks people rock in the city.
Todd Gack / June 25, 2014 at 09:54 pm
Who wrote this?

"Dapper Gentleman"??? - Don Draper/Timeless Style would never be caught wearing anything the asian hipster has on in the first pic. Don Draper would get drunk, beat this guy down with his bow tie, then nail his sister. Queen streets definition of timeless doesn't work in the real world, by which I mean any real office building or grownups over the age of 30.

What's Not Timeless:
1. Jacket is too short.
2. Polka Dot Socks.
3. Bow Tie.
4. Bright re grocery bag.
5. Lapel flower.
6. Flood pants.

KT / June 25, 2014 at 10:09 pm
I wouldn't date a a man dressed like any of them (except maybe Mr. Hip Hop, whixh doesn't really look hip hoppy to me at all). Avant-garde man looks like he crawled out of a discount bin at Goodwill and the rest are more feminine than I am.
Who exactly do these people represent? Morley of the men in the city dress nothing like these guys unless you only hang out on Queen West.
Anonymous replying to a comment from Confused / June 25, 2014 at 11:02 pm
What's wrong with men looking feminine? It's not like women have cornered the market on fashion.

If ladies can wear masculine-inspired clothing, it's fair game for men to wear the reverse. Clothes are just clothes; the only difference between clothing "for women" and clothing "for men" is the way they're marketed: segregating the market is a sales ploy.

Sure, you can argue that there's a difference in size and that clothes are tailed for different body type, but Conchita Wurst looked gorgeous in that gown at this year's Eurovision contest and I've seen many a lady rock double-monks!
mrsP / June 26, 2014 at 12:19 am
I'd love to sit on the lap of Mr Bay St.
He's smokin'!
me replying to a comment from Alex / June 26, 2014 at 12:49 am
not all of the pics are current.
Yvonne / June 26, 2014 at 02:25 am
Pathetic!!! These clowns look SO SAD!!!!
Bi Bimbop / June 26, 2014 at 08:12 am
Can we just collectively retire the bowtie? Guys, enough. It's over.
AMG / June 26, 2014 at 09:59 am
Since when is it "cool" or "fashionable" to dress like Pee Wee Herman?
Toronto is so fucking pretentious, it makes me want to leave.
Rayray replying to a comment from AMG / June 26, 2014 at 10:36 am
Sad part is that Toronto tries to be pretentious but fails greatly.
sw replying to a comment from D Money / June 26, 2014 at 01:56 pm
I actually just full-on LOLed at my desk because of this comment. Snaps for you!!
donald / June 26, 2014 at 05:50 pm
All these guys look silly
Lisa / June 26, 2014 at 08:17 pm
These are styles that are popular everywhere not sure why all the commenters are getting their panties in a bunch.

Personally, I enjoy bay st casual, hip hop, or the don draper/suited look on my men.

ohmy / June 26, 2014 at 11:40 pm
Too tight jacket with too tight and short pants gives that: "My how you've grown" look. Grandmothers are fond of it.
@Rayray / June 26, 2014 at 11:41 pm
Well, Ray, you for one seem slavishly devoted to reading Toronto news and making pretentious comments. I think the sad one is actually you! haha!
BCee / June 26, 2014 at 11:49 pm
Thank you BlogTO. I could not hate my city more with this. Pretentious, douchebag f**king hipsters. No wonder the rest of Canada hates us...
Similar / June 28, 2014 at 06:09 am
Jesus fuck. You guys. Separate the pieces from the whole. Look at the entirety of an ensemble and glean the ideas that will work for YOUR collection. All this hate towards these looks, yet there's so much inspiration to extract; whether it's a hair style, hat, shew, slack... man, if these guys have the confidence to rock this gear - in this way - no one can say shit. I'm a straight male, but I'd give every one of these mangos the up and down if I saw them on the street. Fuck it, I'd put Bay St. Casual's dick in my mouth for at least 25 seconds. Maximum 40.
Anne / June 28, 2014 at 08:16 am
I'm a hipster
To the hate-filled BCee / June 28, 2014 at 10:51 am
Earth to BCee, no one gives a flying fig whether the rest of Canada "hates" us or not. The fact that many who move here from places like "BCee" and bring with them all their petty hates/jealousies/biases toward Toronto instead of leaving them back home is their problem, not ours. If you feel so filled with hatred toward your alleged city, then please feel free to move back to the Wet Coast; although in reality we all know that you actually live there and scan our news everyday because nothing of interest happens where you live.

Truly it sounds like Blandcouver is your kind of town. Everyone there has that "just got back from a camping trip" look.
fts / June 29, 2014 at 01:44 am
A perfect representation of everything that's wrong in Toronto. What a bunch of lost souls.
jamie / June 29, 2014 at 02:04 am
sadness is what they fell, souls are what they lack

help may be on the way, but alas 10 years has come an gone...

their brains need porridge no doubt

*runs like sonic so fast that everything becomes slow motion for no reason*

ya, i supremed dat ;) :)

Resin Wicker Furniture / June 29, 2014 at 10:45 am
The wedding plans even met with disapproval from Spain's royal family although King Juan Carlos
eventually gave his blessing to the couple. It's
got that furniture + tv package deals greyish look. Bagley received compensation valued at
$2. Place something between the item and the furniture on a regular basis,
being able to easily find an affordable option. However its uniqueness
beauty is unmatched. The single most popular place to purchase furnishings that may go properly with your entire
Pascal de / July 1, 2014 at 11:39 pm
Is it just me, or do most of these whiny "I HATE TORONTO" comments sound like the same loser with different names? What kind of Power Douche(™) lives somewhere that they hate?
Angela / November 14, 2014 at 12:10 pm
When Ioriginally commented I clicked the "Notify me when new comments are added" checkbox
and now each ime a comment is added I get three emails with the same comment.
Is tere any wway you can remove me from that service?
Christina / November 17, 2014 at 09:48 pm
BlogTo has it all wrong when it comes to "fitted a fitted jacket should be." The buttoned button barely makes it through, with stretch creases painfully visible on the sides. And if you look at just below his shoulders, the material is puckering in a way that indicates it's too tight around his biceps/triceps.

A well-fitting jacket should hug the figure, not close it off like sun-dried sausage casing.
Real / November 22, 2014 at 09:00 pm
the comments on here are so sad. This is exactly why Toronto isn't close to being a world class city. New York and London ooze creativity and style. Toronto people get all antsy about someone who isn't in a grey gap sweater and dad jeans. Grow some balls you bunch of losers, if these outfits scare you, you're a repressed tight ass cunt. Get real.
Noel / November 22, 2014 at 09:33 pm
My styles are Classic Dapper (after Denzel, Clooney, Poitier, Carey Grant, Humphrey Bogart etc.), 'Hood Casual, Next Gen Futuristic, Modern Athletic, Plain T and Jeans, Caribbean Stylee, Just-Chillin'-At-Home, 25/8/366, and occasionally Self-Styled Eclectic :) ... nope, they're not on the list lol ... OK, maybe New School Funk when I feel like it ...
Corey / November 22, 2014 at 10:10 pm
This is horrible. I wanna puke.
Frances / November 22, 2014 at 10:37 pm
Mr. Bay Street all the way baby!
iluvmen replying to a comment from iliveattheverve / November 23, 2014 at 12:38 am
lol... how?
Ninja / November 23, 2014 at 04:44 am
What's happened to you Your usefulness has dropped significantly. Boo and boo once more.
Danielle / November 23, 2014 at 08:35 am
To the author: please don't pay attention to the ignorant comments! To those who have problems with this post: there are plenty of very pleasant suburban options for you to choose from - Thornhill, Mississauga, Brampton, Oakville.

This was one of the best street fashion spreads on blogTO - I thoroughly enjoyed the descriptions (and thought they were unbelievably accurate) and admired the styles.

So many of the photos would not be out of place in a high-fashion magazine.

The clean hip-hop is by far my favourite - swoon. GUY #8 also has so much personality without compromising on style.

I also love the sunglasses in "pop art eclectic" (as well as the title you gave him).

Kudos for this, and let's see more.

Stay creative, Toronto.

Danielle / November 23, 2014 at 08:41 am
PS And the YouTube socks contrasted with what seems to be a nod to a middle-eastern keffiyeh scarf. Such a brilliant story told (intentionally or accidentally) in one outfit.
VictorS / November 23, 2014 at 09:43 am
Oh, my Y chromosomes are hurting. Hurting bad. Men, as we knew them, are now 50+ and vanishing from existence. How sad our kind have been wussified and man-childed to near extinction.
VictorS replying to a comment from shubjero / November 23, 2014 at 09:45 am
Hahahahhahhahahaa! BWAAHHAHAHHAAHAAAAA! Awesome post.
droney / November 23, 2014 at 10:14 am
Oufff....mostly is a lost of people who dont have jobs. Its easy to dress weird when i dont have to do stuff.
droney / November 23, 2014 at 10:15 am
A simple understated classic male slightly 50s inspired should be on the list. It looks good and is workable
Elizabeth replying to a comment from go figure. / November 23, 2014 at 08:16 pm
I just hope he's got small feet, otherwise how does he get those pants on and off?
Elizabeth replying to a comment from Danielle / November 23, 2014 at 08:17 pm
Everyone is incredibly influenced by this post, and ashamed of themselves.
Shay / November 24, 2014 at 03:56 am
These fashions don't even speak to the outiside of 20-30 set. And they don't properly describe themselves. They're mostly creations just tie this article. There are barely 6 styles in this city for men and it's high time will do change that! This is a bit of x kind effort at that but kudos on the concept.
Mike / November 20, 2015 at 12:20 pm
Other Cities: Montreal