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If you didn’t own a bucket hat, platform sneakers, or at least one questionable windbreaker in the ‘90s, were you even there?
This decade was a melting pot of bold choices, blending everything from stylish streetwear to high-glam supermodel moments. Thanks to MTV, fashion magazines, and the rise of the web, inspiration traveled faster than ever, making ‘90s styles a mix of preppy pieces and grungy self-expression.
From Tommy Hilfiger’s sporty aesthetic to Versace’s opulent prints, designers set the tone for an era that still influences wardrobes today. But the best ‘90s fashion isn’t just nostalgic—it’s surprisingly wearable.
If you’re ready to update your closet with fashion styles from the ‘90s, read on for 11 of the era’s top outfits and learn how to wear them today.
Channel our favorite fashion trends from the 90s with these 11 outfit ideas.
Originally inspired by lingerie, slip dresses became the epitome of “model-off-duty” styles, often paired with barely there heels and a simple clutch. They dominated 1990s fashion thanks to icons like Kate Moss and Carolyn Bessette-Kennedy.
Add this look to your rotation by wearing a slip dress, leather jacket, and combat boots. In summer, slips work well with strappy sandals and delicate jewelry. For a cold-weather outfit, layer the dress over a fitted turtleneck.
Few ‘90s garments were as comfortable as baggy jeans. From hip-hop artists like Aaliyah to royalty like Princess Diana, everyone in this era embraced jeans in different washes. High-waisted, five-pocket blue jeans were particularly popular before 2000s fashion came on the scene with their extremely low-rise options.
To wear baggy jeans today, balance their volume with a crop top and sneakers, or tuck in a structured button-up shirt and add heeled boots. For extra ‘90s nostalgia, accessorize with a bucket hat and a mini shoulder bag.
Grunge fashion was inspired by the underground music scene. Flannel shirts, ripped jeans, and combat boots—made famous by stars like Kurt Cobain and Drew Barrymore—defined the aesthetic.
Put a grunge spin on your personal aesthetic by layering a plaid shirt over a band tee and pairing it with distressed, straight-leg jeans. Finish the outfit with Dr. Martens and a leather crossbody bag. For a more polished approach, swap the flannel and band T-shirt for an oversized blazer and slip dress.
‘90s fashion style had a preppy twist thanks to the movie Clueless. Think plaid skirt suits, knee-high socks, and pastel cardigans like Cher Horowitz wears in the film.
The key to nailing this look today is mixing classic and modern elements. Pair a fitted polo with a sweater vest, a pleated mini skirt, and a houndstooth blazer. Loafers or Mary Janes with white, frilly socks complete the outfit.
A leather jacket was the go-to layering piece of the ‘90s, worn by Winona Ryder, Kate Moss, and every actor on Friends. The beauty of this staple is its versatility—it works with everything from slip dresses to baggy jeans and beyond.
Complete this throwback look by pairing a cropped leather jacket with black jeans, a black tee, and chunky sneakers. You can also layer an oversized moto jacket over a hoodie and bike shorts or leggings.
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The ‘90s were all about showing some skin, and crop tops became a year-round favorite. They were everywhere, from Britney Spears to the Spice Girls.
Pair a fitted, ribbed crop top with high-waisted mom jeans and sneakers for a casual, ‘90s-inspired look. For a sportier vibe, layer a colorful windbreaker over a cropped tank and leggings.
Street style met practicality in the ‘90s with the rise of cargo pants. Initially worn by skaters and hip-hop artists, these bottoms quickly gained popularity, making their way to runways and magazines.
Modern cargo pants embrace the baggy silhouette and endless pocket options. Pair these pants with a fitted tank top and heeled mules to balance out the slouchy shape. You can also wear a cropped hoodie and combat boots to embrace the pants’ original military design.
A list of ‘90s fashion wouldn’t be complete without denim jackets, skirts, and even head-to-toe Canadian tuxedos. Best shown by Britney and Justin’s denim-on-denim red carpet moment in the 2000s, this trend is still wearable today—you just have to find the right balance of colors and textures.
Our go-to is a pair of straight-leg jeans in a classic mid-wash with a fitted white T-shirt. Create contrast with a jean jacket in a slightly different shade—darker on top and lighter on the bottom works well. Tuck in the shirt and add a black or brown belt to break up the denim. Keep the accessories simple with white sneakers and a mini shoulder bag.
Nothing screams ‘90s fashion like a choker necklace. Whether it’s a black velvet band, a tattoo choker, or a delicate chain, this accessory was a must-have in this era.
Opt for a sleek gold or pearl choker to elevate a slip dress, or lean into the grunge aesthetic with a thick leather version, an oversized band tee, and ripped jeans.
Princess Diana made bike shorts an unlikely ‘90s staple. She was frequently photographed wearing them with oversized sweatshirts and white sneakers.
Today, this athleisure staple works just as well for casual wear when paired with an oversized crewneck sweater and chunky shoes. To elevate the look, wear bike shorts with a crop top, an oversized blazer, and a clutch.
The bucket hat was initially designed as a practical accessory for fishermen and outdoor workers. By the ‘90s, it had evolved into a closet essential, worn by hip-hop icons and skaters alike.
Lean into this hat’s relaxed vibe by pairing a neutral-toned or denim bucket hat with a fitted crop top and high-waisted, baggy jeans. To finish getting ready, layer an oversized, open button-up shirt on top and grab a mini shoulder bag.
The best ‘90s fashion is back, and we couldn’t be more excited. Whether you’re drawn to baggy jeans, slip dresses, or preppy plaid, these outfits prove great fashion never truly goes out of style.
If you want to shop sustainably, thrift iconic ‘90s pieces on ThredUp at budget-friendly prices. Explore our curated selection of preloved crop tops, bike shorts, and denim to stock your closet while giving secondhand fashion a new life.
Need help styling your finds? ThredUp’s AI-driven Style Chat feature can provide outfit inspiration and personalized suggestions to discover the perfect ‘90s-inspired pieces.
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