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STYLE AND CULTURE
HOW TO DO: 90s FASHION
By Ayis Stephen-Diver, 19 January 2026
The 90s were pretty iconic: The Matrix, The Notorious B.I.G, Friends, Oasis, Furbys…the list goes on. With this came equally iconic fashion moments, courtesy of the decade’s most stylish. The cycle always comes back around, and for 2026 we’re seeing the comeback of 90s fashion, from denim and grungy looks to hip-hop style. Whether you’re into true vintage looks or referencing celebrity style in your own way, we’ve rounded up our five favourite ways to nail 90s-style clothing.
#1: OVERSIZED TAILORING
Picture: Getty.
Keanu Reeves, Matthew Perry and Matt Damon are just a handful of the celebs that always considered tailoring when it came to their 90s looks. For your 90s-inspired outfits, follow their styling tips: wear T-shirts under two-piece suits or oversized blazers with baggy denim – perfect for occasions and off-duty days.
#2: LEATHER JACKETS
Picture: Getty.
If true 1990s men's fashion is your vibe, try a vintage-style leather jacket like Brad Pitt’s. A staple in grunge fashion, distressed leather jackets give off an effortless feel – as does all the metal hardware. If you like something a bit more polished, try a leather blazer like Jeff Goldblum, or if you want to make it more modern then opt for a Harrington – wear it relaxed with your favourite jeans.
#3: SPORTSWEAR
Picture: Getty.
Will Smith always loved colourful 90s outfits, but he really came into his own during his Fresh Prince era. Track sets like this were the norm, and everyone loved a heavy brand moment. From Tommy Hilfiger to sports icons like Nike and adidas, graphic tees and hoodies were the go-tos. If you want to really embrace the 90s vibe, shop our selection of vintage 90s clothes.
#4: PREPPY LOOKS
Picture: Getty.
Campus style is an ever-evolving aesthetic, with different elements becoming popular at different times. Carlton from The Fresh Prince might have gone full fraternity-prep, but for others, campus style was nothing more than a tucked-in tee and slim jeans. This Denzel Washington moment is a more off-duty take on the aesthetic. The dad jeans, the baseball cap, the satchel – it’s a simple outfit that’s easy to replicate, and so classic that it’ll never fall out of favour.
#5: STREETWEAR
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Picture: Getty.
Streetwear and hip-hop will forever be intertwined. From Air Jordans to Timberlands and all the oversized, sporty silhouettes, they’ve inspired everyday wardrobes and 90s-theme party outfits alike. Icons like Tupac and Biggie are synonymous with hip-hop fashion and will forever be sources of inspo. Speaking of Timberlands, it’s nothing new that the boots have come back around. They’re mega comfy and will last you a lifetime, so no wonder every East Coast hip-hop star was seen in them. Wear yours with baggy jeans, a plain tee and a utility gilet to bring the vibe up to date.
WHAT WERE THE MOST POPULAR 90S OUTFITS FOR MEN?
A few 90s outfit combos have transcended aesthetics and subcultures. One key look has to be the oversized T-shirt-and-baggy jeans duo. If your T-shirt had some sort of nostalgic graphic plastered on the front, your outfit would guarantee nods of approval at any function.
HOW CAN MEN RECREATE A 90S STREETWEAR LOOK?
Lots of the brands we now consider household names really made their mark in the 90s – including Timberland, Air Jordan, Tommy Hilfiger, Champion and so many more. So if you're going to start anywhere, start with an iconic label. Then just copy the look from your favourite celebrity above.
Pictures: ASOS
HOW CAN MEN AVOID OVERDOING A 90S LOOK?
There isn’t any way to ‘overdo’ 90s style per se, especially as current fashion trends are constantly circling back to previous eras. But to avoid looking like you’re costuming the culture, modern pieces will balance out your look. For example, wear your Timberlands with jorts, or consider denim that isn’t just baggy – like barrel-leg and balloon silhouettes, AKA 2026’s signature styles.
Picture: Getty
WHAT COLOURS WERE POPULAR IN 90S MENS FASHION?
In the 90s, everyday wardrobes and red carpets leaned towards minimalism – think charcoal grey, powder blue, navy, white and black. However, the decade had a sentimental spot reserved for the iconic red, white and blue palette – which Tommy Hilfiger’s domination of the era definitely had something to do with.
