Guide To 90’s Style Men’s Clothing and Outfits

Over the last few years, there has been a fashion renaissance in 90s trends, thanks to style trendsetters and uber influencers. Influenced by hip-hop bands, rockstars, and celebrities, the ’90s inspired some cool trends that have defined the fashion scene.

Designers and fashion experts are bringing back those trends of the “young and careless” times, giving their own interpretation. 90s aesthetics from baggy jeans and oversized t-shirts to bucket hats, Timberland boots, and gold chains, 90’s men’s fashion features everything.

Whether you’re attending a ’90s theme party, or want to incorporate a vintage aesthetic and an old-school vibe into your daily looks, here’s everything you will need. Keep reading to see the ultimate guide to 90s clothes.

Graphic Tees

‘90s hip-hop fashion was largely defined by oversized fits and baggy silhouettes. The motto was the bigger – the better. Graphic, band, and skate t-shirts became a staple of ’90s street fashion and were associated with the ”skater boy style”‘. In case you’re wondering how to style an oversized graphic tee, the options are endless.

You can wear an acid wash graphic tee with loose fit, distressed jeans and Converse sneakers to achieve the ultimate vintage look, or mix and match it with modern tailored pants and chunky shoes. Prefer a tee with a classic crew-neck cut that you can layer under a plaid overshirt and leave it unbuttoned.

Carhartt Workwear Pants

Cargo pants and work pants, such as those from Dickies and Carhartt have long been a go-to for those looking to rock the skater vintage look. All you need to do is choose a cropped, wide-leg design or cuff a straight-leg style to a couple of inches above your ankles.

Not only they are easy to style but also very practical with all these pockets and zippers. Coming in different styles and patterns, from oversized and baggy to slim and tapered fits. Opt for camo or army cargo pants, if you’re more to into the hip-hop aesthetic.

Style a pair of loose-fit military cargo pants with a white top underneath. Add a denim jacket on top, a baseball cap and a thin gold necklace.


Timberland, Dr.Martens, Converse, and Nike – all of these labels were widely popular in the ’90s. Whether it is a suede Timberland boot, a high-top Air Jordan sneaker, or a low-top Converse shoe, you can’t go wrong sticking to the classic.

Oversized Sweatshirts

During the early ‘90s hip-hop culture, brands like Champion, Nike, Adidas, Fila, Fubu, Supreme and Phat Farm&Wu Wear set the trends for urban streetwear.

The Nike hoodie with the iconic swoosh, the Adidas crewneck sweatshirt, and the Supreme pullover with the famous box logo, were in every guy’s wardrobe. They can be paired with cargo pants, baggy jeans, and cropped trousers, and even with a puffer jacket on top for winter.

Wear a white shirt underneath a crewneck sweatshirt and let the collar out to achieve a preppy street look. Complete with chinos and Air jordans to add more interest.

Bombers Jackets

Bomber jackets, also known as flight jackets, are always connected with ’90s hip hop street fashion. You can opt for a boxy fit bomber jacket, that you can wear over a plain t-shirt.

For a street edgy look, you can wear black denim jeans and leather combat boots. Remember that a good-fitting bomber jacket should be snug on your shoulders while staying slim throughout the body and sleeves.


Hip-hop style entered the mainstream in the ’90s, and with it came Kangol caps, bucket hats and snapback hats. It was the Kangol brand that dominated the hip hop style, featuring bucket hats and baseball caps on famous rappers of that time.

Although the bucket hat and the snapback hat first came along with hip hop fashion, they soon became iconic retro pieces. They often featured logos or statements from famous athletic teams and brands and can be worn with all streetwear outfits.

Style one with a pair of jeans, a hoodie and a color block windbreaker or with a tracksuit set and chunky ‘Dad’ sneakers.

Flannel shirt

A longtime staple of every man’s wardrobe, a flannel shirt is the most versatile piece that you can own. Hip Hop artists used to wear flannel shirts and plaid jackets in casual looks back in the ’90s.

You can style it over a printed tee and leave it unbuttoned or tie it to the waist for a more street look. Create a neutral-toned look with brown pants a basic white tee and complete with a beige flannel shirt and a pair of Converse sneakers.

Baggy Jeans

When trying to master the vintage street style look, you can never go wrong with a pair of jeans. In the ’90s, brands like Levi’s, Lee, Calvin Klein, Phat Farm and FUBU were leading the way in denim as part of the street fashion wardrobe.

Artists like Tupac and Eazy-E often matched baggy jeans with oversized denim jackets to maintain the 90s fashion vibe. From jackets to jeans and overalls, denim was a clothing staple to every man’s wardrobe.

You can mix and match different washes of denim to create a head-to-toe denim appearance, or style a pair of blue baggy jeans with a bright color sweatshirt and white sneakers.


The classic windbreaker with the bold block colors is making a huge comeback from the 90s. To achieve a full vintage look, tuck a white t-shirt into high-waisted jeans dad fit jeans and add a lightweight, colorful windbreaker on top.

Let the jacket stand out as the main piece of the look and finish off with a pair of white sneakers.


First worn by rappers and hip-hop artists, the bandana was a symbol of gang culture. Since then, it has become a trendy fashion accessory that can be styled in many ways around the head, neck, arm, or wrist.

It can complement your look, especially when you want to pull off a retro vibe. You can match the bandana’s print or color to your shoes or create a monochromatic outfit and add a bright-colored bandana.