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90’s Fashion Guide: How to Get The 1990’s Style

Will Smith Overalls

If you follow the latest trends in men’s fashion, then you’re probably feeling a bit nostalgic for the ’90s. Much like the age of The Fresh Prince and Clueless, this season’s menswear collections featured plenty of boxier silhouettes, athleisure, and minimalist basics paired in myriad ways that would make Will Smith proud.

There’s probably some element of your personal style that has been inspired by the era (we’re living in track pants and hoodies these days, after all). That’s why we rounded up some of the most notable trends of the ’90s, and the best pieces to buy to relieve that decade with a modern approach.

Bucket Hats

The Kangol bucket hat was a right of passage for any rapper looking to make it in the music industry, so of course a piece so synonymous with the ’90s has made its way back into our current trends. Nowadays, the bucket hat can be worn a variety of ways from streetwear to casual looks.

Kangol Bermuda Bucket Hat — $63

Kangol Bermuda Bucket Hat

If you want to really relive go with the OG bucket brand hat worn by rappers like LL Cool J.

Nike Washed Bucket Hat — $32

Nike Washed Bucket Hat

If you’re going for a more athletic approach to the bucket hat trend Nike has a great option in a variety of colors.

Burberry Checked Cotton-Blend Twill Bucket Hat — $320

Burberry Checked Cotton-Blend Twill Bucket Hat

The bucket hat has made its way into high fashion, rendered in the instantly recognizable Burberry Plaid.

Stussy Stock Bucket Hat — $50

Stussy Stock Bucket Hat

Streetwear brand Stussy’s bucket hat is perfect for an authentic ’90s look.


The turtleneck was a go-to look for teeny heartthrobs like Justin Timberlake, to alpha males like The Rock. These days, Turtlenecks have become a uniform for creative types and tech guys. Plus, they look great on camera.

Neiman Marcus Men’s Chunky Cable-Knit Turtleneck Sweater — $495

Neiman Marcus Men's Chunky Cable-Knit Turtleneck Sweater

This knit channels ’90s Justin Timberlake’s fit at the MTV Video Music Awards.

Topman Black Ribbed Roll Neck Jumper — $42

Topman Black Ribbed Roll Neck Jumper

If you’re going for the ’90s prep look. you can’t go wrong with this ribbed jumper.

Asos New Look Roll Neck Sweater in Black — $30

Remember the photo of The Rock with the chain … pretty close huh?

Uniqlo Men’s Soft Touch Turtleneck — $20

Uniqlo Men's Soft Touch Turtleneck

A lightweight option with breathable material to kick start the season.


Probably the most recognized style moment of the ’90s is a good pair of denim overalls (always with one strap down, of course). This look was worn by some of the most notable men of the era, from Will Smith to Tupac.

Shein Men Ripped Slant Pocket Denim Overall — $33

Shein Men Ripped Slant Pocket Denim Overall

A modern take on classic overalls with a slim bottom.

Forever 21 Slim-Fit Utility Overalls — $35

Forever 21 Slim-Fit Utility Overalls

For those interested in adding a pop of color into their wardrobe.

Carhartt Duck Bib Overalls — $80

The durable and functional option while staying on trend.

Levi’s Denim Overalls — $66

Levi's Denim Overall

The classic denim overalls for the signature ’90s era look.

Basic White Tee

Arguably the most ubiquitous staple of the ’90s is the white tee. Although basic alone, this t-shirt is super versatile and can be paired with anything from jeans to a biker jacket.

Urban Outfitters Recycled Cotton Crew Neck Tee — $15

Urban Outfitters Recycled Cotton Crew Neck Tee

Made from recycled cotton, not only will you look good, but feel good.

Bleusalt The Men’s High-T — $100

Bleusalt The Men's High-T

An ultra-soft tee that you’ll never want to take off.

AllSaints Aldwin Crew T-Shirt — $30

AllSaints Aldwin Crew T-Shirt

Relaxed fit with a little texture in case you don’t want to go too basic.

Banana Republic White T-Shirt — $18

Banana Republic White T-Shirt

Doesn’t get more classic than this one.

Chunky boots

The ’90s were all about elevating style, down to the heels. Chunky footwear was popularized by the decade’s grunge scene, which was all about boosting one’s height. Case in point: It was also the same era when Doc Martens took off. Today, the all-American boot brand is still going strong, and has entered the mainstream. Now you can see guys in preppy and normcore styles wearing these thick-soled duds.

Dr. Martens Black Mono 1460 Boots — $145

We’re pretty sure these never went out of style.

Dr. Martens Black Jadon Hi Boots — $180

Dr. Martens Black Jadon Hi Boots

The yellow stitching screams ’90s grunge era.

Bottega Veneta Slip-On High-Top Boots — $1,100

Bottega Veneta Slip-On High-Top Boots

Easily pair with baggy jeans for a casual look or slim-fit dress pants for a more tailored look.

Asos Design Apricot Premium Leather Chunky Zip Front Boots in Black — $135

Add another level of ‘cool’ with a zipper hardware look.


Another hat style that was popularized by ’90s rappers was the snapback. A lightweight accessory that could be paired with just about anything, snapbacks are typically adorned with a logo or phrase that these celebs “repped.” Today, we still see people wear these baseball caps as a way to show their brand loyalty or promote their merch.

Corridor New York New York Cap — $45

The birthplace place of Rap, therefore the birthplace of the popularity of the snapback.

Rhude Black and Red Pit Stop Trucker Cap — $165

Rhude Black and Red Pit Stop Trucker Cap

LA streetwear brand Rhude pays homage to the ’90s snapback with this merch-style hat.

CCS Thrasher Oval Snapback Hat — $25

No brainer for ’90s fashion to incorporate a Thrasher hat into your wardrobe.

Bad Birdie Bad “Rope” Hat — $30

Bad Birdie Bad "Rope" Hat
The ’90s were all about being a ‘Bad Boy’ so why not let everyone know how ’90s you are by wearing it on your head?

Belt Bags

In the past few years, belt bags have been everywhere. Also known as fanny packs, these were worn by guys like The Rock, and were usually paired with a turtleneck and denim jeans. Today, belt bags have into a streetwear staple.

Eastpak Ssense Exclusive Black XL Springer Pouch — $40

Eastpak SSENSE Exclusive Black XL Springer Pouch

Eastpak and Ssense’s collaboration may make this the most ’90s belt bag on the market.

Fiorucci Angels Bumbag Red — $63

Fiorucci Angels Bumbag Red

This belt bag will complete your nostalgic look with the signature Fiorucci angel motif.

A.P.C Rebound Hip Bag — $125

A.P.C Rebound Hip Bag

A.P.C’s  XL belt bag is perfect to hold all your ring pops and Dungaroo’s.

Saint Laurent Classic Belt Bag — $870

Saint Laurent Classic Belt Bag
A high fashion take on the classic belt bag.

Editors' Recommendations

Ty Gaskins
Ty Gaskins is a Writer, Stylist, and Public Relations Professional based in New York City. Originally from Virginia Beach…
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