From Ross’s geeky attire in F.R.I.E.N.D.S. to Will Smith’s sleek streetwear, 90s fashion played with contrasts — bold and minimalist, preppy and punk, sleek sportswear and streetwear. It was about expressing individuality and personal style, and menswear was no exception.
Growing up, you may recall your dad’s grunge or preppy look during the Nineties. It was a time when fashion made a bold statement and everyone wanted to look different. Music was also a driving force in men’s fashion, with hip-hop and grunge leading the way. Tupac and Biggie Smalls popularised the hip-hop look with oversized clothing, gold chains, and baseball caps, while Kurt Cobain introduced a laid-back, flannel-shirt aesthetic.
As the fashion industry continues to evolve, it’s likely that we’ll see more 90s-inspired trends emerge, from high-waist jeans to bold accessories. Whether you’re a fan of hip-hop, grunge or old-school TV shows, there’s no denying the significant influence that 90s men’s fashion has had on contemporary style with its comeback led by fashion brands Burberry, Gucci, Tom Ford and Valentino.
Key Elements of 90s Men’s Fashion
- Loose-fitting, wide-leg denim and multi-pocketed cargo pants were staple streetwear styles.
- Bold prints, band logos and graphic tees from Tommy Hilfiger, FUBU, and Nike dominated casual-wear.
- Inspired by the grunge movement, plaid flannel shirts were worn unbuttoned over T-shirts.
- Colour-blocked nylon windbreakers and tracksuits from brands like Adidas, Nike, and Fila were popular.
- Worn backward or tilted, snapbacks and bucket hats often featured sports teams or brand logos.
- Light-wash denim jackets paired with jeans were inspired by pop icons like Tupac and Justin Timberlake.
- High-top sneakers like Air Jordans, skate shoes and rugged Timberland boots completed urban looks.
- Black leather biker jackets were essential for rock and alternative fashion.
- Denim or corduroy overalls, often worn with one strap undone, defined hip-hop and casual wear.
- Bold branded sportswear from Tommy Hilfiger, Champion, and Ralph Lauren Polo Sport were staples.
Top 5 Iconic Styling Ideas From Popular 1990s Shows and Films
The Grunge Look – Inspired by F.R.I.E.N.D.S. (Chandler and Ross)
The ‘90s grunge style was all about effortless layering, plaid flannel shirts, baggy jeans and boots. Seen frequently on popular television show F.R.I.E.N.D.S., particularly on Chandler and Ross in their casual wear, this look captured the laid-back aesthetic of the decade. To modernise it, wear a fitted plaid over-shirt, straight-leg jeans and a clean pair of white sneakers or Chelsea boots for a sleek, nostalgic vibe.
The ‘90s grunge style was all about effortless layering, plaid flannel shirts, baggy jeans and boots. Image: NBC.
Preppy Chic – Inspired by Clueless (Cher and Dionne’s Male Counterparts)
The preppy aesthetic was highlighted in the teenage film Clueless, with rich textures, structured blazers, sweater vests and polished trousers. The male characters embraced classic Ralph Lauren-style dressing with polo shirts and khakis. Today, we can update this style with a slim-fit blazer over a crew-neck sweater, tailored chinos, and loafers for a contemporary look that nods to ‘90s prep.
Minimalist Monochrome – Inspired by The Matrix (Neo and Trinity)
The all-black aesthetic of The Matrix became a defining look of late ‘90s fashion. Long leather coats, futuristic sunglasses and fitted black ensembles created a timeless, edgy style. A modern approach would be an all-black look featuring a tailored trench coat, slim-fit trousers, and angular sunglasses — an effortless yet powerful look for streetwear or evening wear.
Sporty Streetwear – Inspired by The Fresh Prince of Bel-Air (Will Smith)
Will Smith’s bold vibrant outfits in the film, The Fresh Prince of Bel-Air. epitomised ‘90s street fashion. Oversized graphic tees, neon windbreakers and snapback caps made his look youthful and energetic. To wear this today, pair a vintage-style windbreaker with slim joggers and high-top sneakers, keeping colours bright but coordinated.
Will Smith’s bold vibrant outfits in the film, The Fresh Prince of Bel-Air. ILLUSTRATES ‘90s street fashion. Image: NBC
Hip-Hop Baggy Style – Inspired by Boyz n the Hood (Tre and Doughboy)
The hip-hop-inspired style of Boyz n the Hood featured oversized hoodies, baggy jeans, and sports jerseys, reflecting the urban fashion movement of the ‘90s. Today, we can adapt this look by balancing proportions—pair an oversized hoodie with relaxed-fit jeans and chunky sneakers while keeping accessories minimal.
Essential 90s Accessories for Men
The 1990s were an era of self-expression and accessories played a key role in defining men’s fashion across subcultures.
- 1. One of the most iconic accessories of the decade was the chain wallet, a staple in skater and punk fashion.
- 2. Beanies and bucket hats became go-to headwear, popularised by grunge musicians like Kurt Cobain and hip-hop artists.
- 3. Choker necklaces, ball chain necklaces, and leather cuffs were embraced by rock and alternative scenes.
- 4. Wraparound sunglasses and small, tinted lenses gained popularity thanks to rave culture and stars like Will Smith in Men in Black.
- 5. Footwear and wrist accessories also defined the 90s aesthetic.
- 6. Chunky sneakers, particularly from brands like Nike and Fila, were worn by everyone from hip-hop fans to skaters, while combat boots and Converse were essential for grunge and punk enthusiasts.
- 7. Slap bracelets, made of flexible metal covered in colorful fabric, were a fun, playful trend that added a nostalgic, carefree vibe.
- 8. Fanny packs, initially seen as practical items, became a streetwear staple, especially in hip-hop circles.
- 9. No 90s look was complete without a bandana, worn in different styles by rockers, hip-hop artists, and even wrestlers.
- 10. Johnny Depp often layered beaded necklaces, silver rings, and leather bracelets. His love for round-lens sunglasses and fedoras further added to his mysterious, vintage-inspired look. Leonardo DiCaprio, on the other hand, embodied the youthful heartthrob aesthetic, frequently seen wearing minimalist silver chains, leather chokers, and beanies, particularly during his early Romeo + Juliet and Titanic years.
Where to Shop for 90s Fashion Today
- High-end streetwear brands like Supreme, Off-White, Fear of God, and Balenciaga offer updated takes on iconic styles from the decade.
- Supreme’s oversized graphic tees, hoodies, and baggy jeans echo the skater and hip-hop influences of the 90s while Off-White incorporates bold logos and industrial-style belts that recall the era’s love for statement accessories.
- Fear of God modernises grunge-inspired looks with distressed denim, flannel layers, and oversized silhouettes.
- Balenciaga brings a designer spin to 90s sneakers, oversized outerwear, and logomania.
- For those who want authentic 90s pieces, vintage and thrift stores like Goodwill, The Salvation Army, and Buffalo Exchange carry oversized flannels, vintage band tees, and classic 90s denim at affordable prices.
- Online platforms like Depop, Grailed, and ThredUp offer curated selections of vintage sportswear, grunge essentials, and rare finds from brands like Tommy Hilfiger, Polo Ralph Lauren, and Levi’s.
- For a budget-friendly approach, high-street brands like Zara, H&M, and Uniqlo offer modern takes on 90s fashion.
- Zara frequently releases oversized denim jackets, straight-leg jeans, and relaxed-fit flannels that capture the grunge and skater aesthetics.
- H&M provides casual streetwear staples, from graphic hoodies to cargo pants.
- Uniqlo focuses on minimalist 90s essentials, such as plain oversized tees, relaxed chinos, and fleece pullovers, ideal for a more understated retro vibe. These brands make it simple to embrace 90s fashion trends while maintaining a contemporary feel.
Conclusion and Final Thoughts
The 1990s was a defining decade for men’s fashion, combining casual-wear with bold statement pieces. From the grunge-inspired flannel shirts and distressed denim of F.R.I.E.N.D.S. to the oversized sportswear and street styles seen on The Fresh Prince of Bel-Air, the era offered a diversified look that continues to influence modern fashion. Whether it was the sleek, all-black aesthetic of The Matrix, the preppy sophistication of Clueless, or the hip-hop styles in Boyz n the Hood, ‘90s menswear celebrated individuality.
Embracing ‘90s fashion doesn’t mean dressing in full throwback outfits—it’s about incorporating elements from the era into the modern wardrobe. Layer a plaid overshirt over a fitted tee, pair vintage-inspired windbreakers with joggers, or opt for sleek monochrome ensembles with contemporary tailoring. The key is to take inspiration from iconic TV shows and films while adapting them to today’s fashion sensibilities. Which ‘90s look from a TV show or film is your favourite? Share in the comments!
Jasmeen Dugal is Associate Editor at FashionABC, contributing her insights on fashion, technology, and sustainability. She brings with herself more than two decades of editorial experience, working for national newspapers and luxury magazines in India.
Jasmeen Dugal has worked with exchange4media as a senior writer contributing articles on the country’s advertising and marketing movements, and then with Condenast India as Net Editor where she helmed Vogue India’s official website in terms of design, layout and daily content. Besides this, she is also an entrepreneur running her own luxury portal, Explosivefashion, which highlights the latest in luxury fashion and hospitality.
