The late 90's and early 00's presented some of Toronto's quirkiest (and perhaps most regrettable) fashion trends. It's difficult to fathom that we once actually thought it was okay to leave the house looking the way we did. To dig through our Facebook Timelines would be a painful task, since we'd likely uncover cringeworthy photos of our past "fashion no-no” moments that we wish never happened.

All fashion trends come and go... For the most part. Heidi Klum said it herself: "In fashion, one day you're in, and the next day, you're out." Some past trends are just so hideous that it's hard to imagine them ever resurfacing today. Never say never, though. I mean, if bucket hats, sweaters-tied-around-the-waist and even fanny packs can make a comeback, so can any of these 18 past fashion fads:


1. Flare pants/bell bottoms

Though these pants were at the height of their popularity in the mid-60's and 70's, they were still trendy in the 90’s. At that time, bell bottoms for women still had prominent flares, whereas the flares for mens pants were reduced to a slimmer and more subtle bootcut. In this day and age, finding someone wearing flare pants in Toronto is a rarity. Unless you're going to Rocking Horse, flare pants are just not much of a good look anymore. Let’s be real - the skinny jean is here to stay.


2. Phat Farms

Once upon a time, Phat Farms were the shoes everybody in Toronto wore on their feet. The brand had been around since 1992, but it really blew up in the early 00's; near the same time Ciara first came onto the scene with “Goodies”. They weren't the worst looking shoes I guess; in fact, they were even kind of Adidas Superstar-esque. But they don't really have a place in today's fashion landscape...  Even The Brunswick House enforced a dress code restriction on them once; having put up signs on its windows that read  "No Urban Wear (e.g., G-Unit, Phat Farm etc)". I guess the only place they belong now is in old C-walk videos, where they were often showcased by teenyboppers in all their fat-tongued glory.


3. Raccoon/fox tails

When it comes to peculiar fashion trends, raccoon/fox tails are definitely up there as one of the most bizarre. The trend began with Louis Vuitton, which originally featured it as a purse accessory during its Spring 2010 runway show. Some Toronto guys joined in on the trend and started hanging tails from the belt hooks on their jeans. Unlike basic accessories like watches and hats that actually serve a functional purpose, raccoon/fox tails are strictly aesthetic. If for some reason you really wanted one, you can still find them being sold in some places in Toronto, like Chichester Canada Inc. on Bloor St. W.


Photo cred - Ratuken Global Market

4. Baggy Dickies pants

In the 90's and 00’s, males wearing baggy pants below the butt cheeks to expose the boxers was a common sight in Toronto. There was a point in time where Dickies were the go-to pants for this style. Most guys today can’t believe they actually spent money on pants that didn’t taper nicely through the legs to the ankles, and they probably won't ever do it again. Then again, Dickies has recently been working to evolve their pants by including a slim and regular fit, so many they may just come back into style. Check out this Dickies feature shot at the Community 54 in Parkdale for more on this development.


5. Plastic choker necklaces

Plastic choker necklaces were once a hit among teenage girls in Toronto. Back then, it was the next best thing to getting a tattoo on your neck. The necklaces also served as a way for some girls to show their inner rockstar during a time when grunge culture was all the rave in Toronto (think Queen's Park in the 90's). It was just the right mix of goth and tame. The only problem was that it made their necks itchy. And it often made them the targets of annoying teenage boys who constantly tried to snap them as a joke. Surprisingly these actually came back recently...but we're hoping it's just a fad.


6. Denim on denim on denim

Britney Spears and Justin Timberlake at the 2001 American Music Awards. That is all (#NeverForget). But seriously though, there was a period in the 90's/00's when wearing full-on jean was actually considered trendy in Toronto. Look through any Fully Alive textbook and you're bound to see some kid wearing some sort of all-jean-inspired outfit. Actually, with the right styling you might still be able to pull off that look today. But in terms of Britney and Justin's look, it's iconic for probably all the wrong reasons... Though, part of being human is learning from your mistakes (and let's face it - that was a big one).


7. Transformable cargo pants

Guys, you know what I'm talking about. These were the pants that you could turn into shorts, with the simple pull of two zippers holding the bottoms of the pants to the shorts. These pants are typically the uniform of choice for Toronto adventurists who like to go on daily hikes; through say, Glen Major Forest and Walker Woods and such. But hiker or not, surely we all had a pair of these at one point or another.  Back then, you could buy them at Stitches for cheap, and you probably wore them everyday.  Too bad your girlfriend would probably never allow you to own a pair of them now... Otherwise, you'd probably wear them all the time, right?


8. Silly bandz

What baller bands were to guys once, silly bandz were to girls. They were fun for girls to collect because they came in all sorts of different shapes and colours. Some time in the 00’s, however, silly bandz were banned at some Toronto schools, especially those under the TCDSB, because there was a concern that they were being used as a way to communicate sexual interests. In that sense, they went from harmless to complicated real quick.


Photo cred - Clavel

9. Roos

Anybody remember Roos? Roos were cool because they were shoes that had pockets. People used to keep their money and TTC tickets in them. The only problem was that they’d need to crouch down and every time they needed to access them, and pulling something out of your shoe made you look a little bit weird. Roos experienced a brief period of success in Toronto and then quickly fizzled out upon the arrival of newer, more hip brands.


10. Bandanas

Bandanas had a few purposes in Toronto back in the day. Some dudes tucked them into the back pocket of their jeans as a way of reppin’ their gangs, back when the whole “Crips vs. Bloods” thing was still going on. For this reason, Torontonians (like this guy) weren't sure whether wearing bandanas around the city was safe. Others wore them to emulate rappers (like Tupac though; not Juelz Santana). Nowadays, it seems like Toronto is over and done with bandanas altogether.


11. The Motorola Razr

Alright, so this isn't really much of a regrettable past fad. In fact, the Razr is even making small appearances today. Even Rihanna sports a Razr nowadays; a pink one, on some of her nights out. It was one of those things that you literally saw everywhere in Toronto. Perhaps the only reason to regret ever having one is the fact that you could have had a much cooler phone like the Sidekick (yes, the Sidekick was super cool back then, okay). You could probably still pick up a Razr at P-Mall; you know, if you're into that retro stuff. I applaud you if you can live completely app-less.


12. Jean skirts

Jean skirts are still worn by girls in Toronto today, but to a much lesser extent as they were in the past. Really, it's what you pair with the jean skirt that either makes your outfit a hit or a miss. In the 90’s and 00’s, jean skirts were part of almost every girl’s wardrobe; likely an influence of Sabrina the Teenage Witch and other similar female figures in pop culture. Nowadays, it’s not so popular; but probably only because Toronto weather can be difficult at times - they’re too hot for summer and too cold for winter.


13. The "Avril Lavigne" phase

Toronto girls were all into Avril Lavigne at some point. Such was a phase of "tank top and cargo pant" combos, colourful Chuck Taylors, black nail polish and Simpleplan. Back then, girls may have had to defend themselves to their moms by claiming that "It's not a phase," or they may have even had a crush on the Sk8r Boi working at the local West49. Whatever the case, most girls were convinced that Avril was everything they wanted to be when they grew up... Then they grew up.


Photo cred - thecoli.com

14. Du-rags

Du-rags are actually used to maintain hold of hairstyle, particularly cornrows or waves, throughout the day or during sleep. However, in the 90’s and 00’s, du-rags emerged in Toronto as a fashion accessory influenced by hip-hop culture. Surely, some guys today regret ever being photographed while wearing one. Even OVO's Niko knows the du-rag days are long and gone: "When I was younger, my style was inspired by hip-hop culture, music, and basketball, like the Allen Iverson-era du-rags and size 40 jeans—those were the good days. But now that I’m a father, I’ve cleaned up and matured a little bit."


15. Bleached hair/frosted tips

Bleached hair and frosted tips are hairstyles that were likely popularized by boy bands. People who weren’t comfortable getting their tips bleached would often buy coloured gel to achieve the same effect. For many of us, bleached hair and frosted tips constituted some of our worst years of hair experimentation. Nowadays, when Torontonians ask for frosted tips, they're probably talking about the amazing cupcakes from Sullivan and Bleeker and not the hairstyle.


16. Double-popped collars

The first thing that comes to mind when I think of double-popped collars is Jersey Shore. This trend actually started out in the 80’s and has since continued in Toronto. The double-popped collar is a style often associated with preppies and frat boys (Queen's students, can you confirm?) Even John Mayer has rocked this style before and it didn't look too bad; though, it’s still weird to wear a polo shirt over another.


17. Crimped hair

Crimped hair is the unofficial symbol of 90’s proms. It was also all the rage back in elementary school. If you really think about it, crimped hair wasn’t all that bad (think Christina Aguilera in Moulin Rouge or Drew Barrymore in Poison Ivy). Even today, crimped hair is slowly re-entering the mainstream – Stella McCartney equipped her runway models with crimped hairstyles at her showcase during Paris Fashion Week in 2014. Regardless, Toronto girls today will probably never consider full-on crimped hair for their Tinder profile pictures.


Photo cred - Auto Straddle

18. Bowl cuts with middle parts

Ryan Gosling rocked this cut back in his Breaker High days, but that doesn’t mean it’ll suit just anyone. It’s definitely a tough one to pull off if you aren't him. Then again, I’d take this haircut over the samurai pony tail hairstyle that's been recently plaguing Toronto any day… Who’s with me?


This list is far from exhaustive. What other past Toronto fashion fads do you remember?

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