90s Men’s Fashion – Best & Worst Examples

90s Fashion

The 90s was a decade of bold fashion choices and distinctive styles that continue to influence the fashion world today. From grunge-inspired ensembles to flamboyant urban looks, the 90s era introduced a diverse range of trends that made a significant impact on men’s fashion. In this article, we’ll take a nostalgic trip back in time to explore the best and worst examples of 90s men’s fashion.

The 90s was an era of experimentation and self-expression through clothing. From oversized denim jackets to neon windbreakers, the fashion landscape was a blend of edgy streetwear and preppy aesthetics. This decade witnessed the rise of iconic trends like baggy jeans, flannel shirts, band t-shirts, and chunky sneakers.

In our exploration of the best 90s men’s fashion, we’ll highlight the timeless trends that have stood the test of time and continue to inspire contemporary fashion. These trends reflect the spirit of the era and offer a unique blend of comfort and style.

However, alongside the fashion hits, the 90s also had its fair share of fashion misses. We’ll delve into the worst examples of 90s men’s fashion, exploring the cringe-worthy trends that may be best left in the past. From questionable pattern combinations to eccentric accessories, we’ll shed light on the fashion choices that missed the mark during this vibrant decade.

Join us as we journey through the best and worst of 90s men’s fashion, celebrating the iconic looks and reflecting on the fashion faux pas that defined the era. Whether you’re seeking inspiration for a throwback outfit or simply curious about the trends that shaped a generation, this article will provide an insightful glimpse into the sartorial world of menswear in the 90s.



We still don’t know how windbreakers fell off the radar. Perfect for a nippy afternoon, but not a risky choice for a warmer day either. And the colours were f***ing epic.



Pagers had a legit day in the sun before they became exclusive property to tired doctors on a long shift. Before Tinder, before MSN, people had to work with a pretty limited system if they wanted a cheeky pash behind the sport shed. If someone paged you ‘143’, you were pretty much in.

Oversized Flannel Shirts


You hated your parents and couldn’t decide between Nevermind and Ten. And were pissed your first girlfriend thought Kurt Cobain was hotter than you. Your uniform of the era was a musty flannel you got dirt cheap at an op shop, and it always kinda stank of old people and moths, no matter how much you washed it.

Biker jackets


Quintessential badass material. It didn’t matter if you never owned a motorcycle. I could never afford one of these jackets, so I still secretly resent the guys who could to this day.

Sweaters Around The Waist


The 80’s did the whole over-the-shoulders thing. In the 90’s, style migrated downwards and spawned an entire generation of kids who never wore jumpers for their intended purpose.

Overalls With Strap Down

overallsYou probably came here just to see this one. No one escaped – not Will Smith, not NSYNC, nobody.

Big Socks


Long socks had a serious moment in the 90’s. The Chili Peppers wore them over their calves (and other stuff). White socks were so damn popular that their purchases probably paid for a few cushy retirements.

Capri Pants


These bad boys were a massive life-saver for those indecisive middle-aged guys who couldn’t commit to a pair of pants but thought it was too nippy to wear shorts (and Rafael Nadal).

Baggy jeans


Walking with style in these was an esoteric art form. You were especially dangerous if they hung about your arse like the skin of a starving elephant.

Ripped Jeans


Ripped jeans sent a powerful message that you were fed up with the system, and probably in a band that sounded how Soundgarden might after twenty beers and a mosh pit punch-on.

½ zip hoodies


If you weren’t wearing it around your waist like a real unit, you were probably suffering from heatstroke because synthetic fibres weren’t left behind in 1989.

Calvin Klein jocks


You just wanted to see a photo of Mark Wahlberg half naked, hey? Fair call.

Sunglasses With Contrast Colour Stems

Plain black Ray Bans were old news (sorry, Tom Cruise). Tricking out sunnies with aqua or pink stems injected a vital pop of colour in an outfit.

Wallet Chains


Necessary kit, because you needed to let everyone know how much serious pocket money you were packing.

NBA jersey


Smell ya later hockey jerseys. American style went truly global, and kids who had never attended an NBA game in their life were wearing NBA swingman’s and defending ‘their’ teams like the last scrap of food on Earth.

Doc Martens


Seeing those iconic yellow stitches was usually confined to angry kids who listened to the Sex Pistols. The 90’s, however, took Doc Martens and handed them to the masses. Listening to grunge and being sulky weren’t mandatory to pull off these rocking stompers.

Tear Away/Popper Pants


Tear away pants gave us an important lesson in living with ever-present, lingering fear (seriously, these guys could lose the plot at any moment). But kids in the 90’s were ruthless. Acquiring Adidas tear-away’s was the sartorial jackpot – until the buttons popped and you flashed everybody.

Bucket Hats

pagersOf all the 90’s things to make a resurgence, it had to be this. Bucket hats were the sole domain of hardass rappers from New York – until high-schoolers got involved. We couldn’t reach LL Cool J for comment.

Fanny packs


Kids needed a place to stash bubble-gum, and spare change they flogged from their parents. God answered. Fanny packs ranged from the discreet and utilitarian, to ones decked out with Power Rangers in battle mode. Modernised today as ‘man-bags’ by metros who are afraid of losing their bus tickets and moisturiser.

Air Jordans


Immortalised by Space Jam and Michael Jordan’s unstoppable brilliance on the courts. The 90’s truly belonged to Air Jordans (but never to me, because I had to make do with Sketchers).

Velcro Wallet

velcroThey opened with that distinctive rip, to let everyone know some heavy spending was going down in the cafeteria. Hearing one today gives you chills (and reminds you of the discreet virtue of a money clip).



Turns out Archer didn’t invent the turtleneck (but don’t tell him that). The history teacher at school wore one, because he thought it made him look distinguished. But really, it looked pretty suss and you really hope you never see that guy again.

Bowl Cuts


Bowl cuts were kinda like the chickenpox of 90’s fashion. Everyone had it at some point, no matter how immune you thought you were. Look at your yearbook photos if you can’t remember. It’s there. Even the guy who played Don Draper had one (Youtube it, seriously).

Pointy Hair


The quintessential boy-band do. You hadn’t truly committed to the look until you wore so much gel that someone could see their reflection in your hair. Jessica Biel still rags on JT for it (not that we feel bad for the bloke).

Bleached Tips


To complement hair that was sharper than a kitchen knife, guys were going all out with bleach. Ask your favourite boy-band front man, or watch an episode of Dawson’s Creek (but just one, that is still binge-worthy).

Luscious Locks


The 90’s opened so many doors for blokes. Men were no longer defined by Don-Draper slick backs or atrocious, brain-searing mullets. It was pretty much open season in the hair department, probably leading to a bunch of poor barbers wondering if they should’ve gone to trade school instead.

Classic Casio Watches


Retro watches, with sick features like games and calculators to keep you entertained while anxiously waited for your Gameboy to recharge. Now sold with hefty mark-ups at commercialised ‘vintage’ stores around Australia.



Casio enjoyed another coup in the 90’s with hard-wearing G-Shock watches, selling 19 million before 2000. Turns out people were after a reliable watch that wouldn’t come off second best in a punch up with a rhinoceros.

Puka Shell Necklaces


A huge hit among both surfer-dudes and teenagers who hadn’t been to the beach in over a year. They were itchy AF and not to be trusted.



Hip hop began to enter the mainstream in the 90’s, and their choice of headwear followed. We’re still not sure how the ‘leaving the sticker on the brim’ trend originated, though. The plot thickens.

Caps At Goofy Angles

willGetting your hands on a snapback was the first step. True sartorial rebellion was wearing caps back to front or on the side. Whatever made you look cool enough to avoid copping a wedgie during recess.



They weren’t just for Donkey Kong. These bad boys were serious style accessories, for serious schoolyard heroes.