Don Cherry’s most bizarre blazers of the season, ranked in order of craziness

Every hockey season, only two things are certain: Don Cherry’s soliloquies will become slightly shoutier, and his suiting choices will become slightly more outrageous. This year was no exception.

This time around, the loud-mouthed Coach’s Corner co-host’s sartorial exploits culminated in an American Psycho–inspired outfit that was, frankly, horrifying to behold. Here, a ranking of his weirdest looks from the past season, from least to most offensive.

15 Cherry kicked off the season at the Hockey World Cup with a relatively inoffensive red-and-white blazer splattered with maple leaves. Even if it looks like he snagged it off the discount rack at a novelty costume store, we can’t really blame him for flexing his patriotism. (Side note: Ron McLean looks like he’s trying oh-so-hard to comprehend whatever’s coming out of Cherry’s mouth.)

14 In October, Cherry channelled Beetlejuice. It would be a pretty tame look for him, except for those angry-looking eyes peeking out from his lapels. And McLean looks positively frightened of what might come next.  

13 Never one to miss a chance to dress in theme, Cherry donned another basic (for him) black-and-white suit, this time adorned with moustaches in honour of Movember.  

12 During the holiday season, Cherry gifted the country with a plethora of ridiculously festive looks, including this blazer, which appears to be inspired by a patchwork quilt (and looks to be a tad too tight around the middle).  

11 Here, he manages to make the ugly Christmas sweater tradition even tackier by reimagining it in suit form.  

10 Cherry flaunted his love for fresh blooms multiple times this season. This particular print is something we’d expect to see on some bathroom wallpaper.  


9 Naturally, he’s also a fan of his namesake fruit. He went ultra-meta by plastering himself in giant cherries—and what appear to be heads of lettuce.  

8 This watercolour-esque floral pattern could almost be trendy if it was on one of this season’s flowing maxi skirts. It’s strangely contradictory on a stuffy double-breasted blazer. (The colour scheme has also been compared to Starbucks’ unicorn frappuccinos.)  

7 This odd choice reminds us of those plastic glow-in-the-dark stars kids used to plaster on their bedroom ceilings.  

6 In retrospect, this Halloween look, featuring bloody skulls, is an eerie foreshadowing of Cherry’s season-ending ensemble.  

5 There are only a few people—like the artist formerly known as Prince—who can pull of purple velvet baroque prints. Cherry is not one of them.  


4 Here’s why it’s unwise to try to celebrate Valentine’s Day and Robbie Burns Day in the same outfit.  

3 Yes, those are jellybeans on his tie and pocket square. No, we don’t know why Cherry busted out the candy-themed accessories to dress up this technicolour coat.  

2 St. Patrick’s Day is already the most obnoxious of holidays in Toronto, even without Cherry dressing up as a full-fledged leprechaun.  

1 At last, there’s this outfit, from Saturday’s game. Surprisingly, even Cherry admits it was a fashion crime. He told the Sun he “had no idea how it looked when he put it on.” From this, we can conclude that Cherry probably doesn’t spend a lot of time scrutinizing himself in the mirror. If that’s the case, there’s only this guy to blame.


Sign up for This City, our free newsletter about everything that matters right now in Toronto politics, sports, business, culture, society and more.

By signing up, you agree to our terms of use and privacy policy.
You may unsubscribe at any time.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.


The Latest

Kiss and Tell: "I started dating my best friend's ex. It ruined our relationship"

Kiss and Tell: “I started dating my best friend’s ex. It ruined our relationship”