4 min readEven before Ryan Murphy’s Love Story: John F. Kennedy Jr. & Carolyn Bessette injected a renewed interest in Carolyn Bessette Kennedy’s style, signs of a ’90s fashion comeback were already there. For the last few years—on the runway and in street style—the industry has embraced minimalism, with quiet luxury and investment dressing endorsing clean lines, neutral palettes, and wardrobe staples meant to outlast micro-trends. More recently, social media has added a more personal layer of nostalgia, as the “What were you like in the ’90s?” prompt has inspired celebrities and everyday users alike to post snapshots from their youth.
Calvin Klein’s tailoring, Donna Karan’s capsule wardrobe, and Ralph Lauren’s sportswear set the tone for the decade’s best fashion (and, some would argue, fashion’s best decade), which balanced timeless elegance with more exuberant dressing: slip dresses, straight-leg jeans, and bias-cut skirts alongside plaid, athleisure, and bucket hats. In pop culture, the era was defined as much by Bessette Kennedy’s stripped-back minimalism as Gwyneth Paltrow’s velvet Gucci suit or Princess Diana’s sweatshirts and bike shorts.
In 2026, the same high-low formula still holds up. But rather than veering into cosplay, today’s best ’90s-inspired outfits capture the decade’s mix of effortless, playful, and timeless appeal but updated for the way we live (and dress) now. With that in mind, think of the images ahead as a styling mood board, and the outfit ideas as a modern interpretation of the decade’s most memorable looks.
High-Rise Jeans
Long revered by fashion insiders, Bessette Kennedy remains a style touchstone for her elegant black-and-white evening looks, slip dress wedding gown, and penchant for fitted skirts. For a more casual take on the late Calvin Klein publicist’s famously restrained style, look to off-duty staples like high-rise denim paired with everything from fine knits to simple tees. Finish with her signature accessories: tiny sunglasses and a chunky headband.
Susanna Chow Roxy Leather Coat
Machete Wide Tortoise Headband
Jimmy Fairly The Emmy Sunglasses
Frame Le Slim Palazzo Jeans
Turtleneck
While Princess Diana’s style impact ranged from off-duty athleisure to the Revenge Dress, it is more her everyday looks that feel especially relevant for spring fashion inspiration. A white turtleneck with white jeans captures that approachable effortlessness, especially when styled with a blazer in a transseasonal color like camel, olive green, or soft gray. Finish the look with classic loafers for a combination that feels refined, unfussy, and modern.
Aritzia Generation Blazer
Mango Simonet Turtleneck Rib Sweater
DL1961 Kristy Cigarette High-Rise Jeans
Miu Miu Leather Penny Loafers
Slip Dress
After first wearing this Donna Karan dress on a date with Mr. Big in the debut season of Sex and the City, Sarah Jessica Parker later stepped out in the iconic mini at the 1997 VH1 Vogue Fashion Awards, cementing it as one of the decade’s most iconic looks. Take SJP’s lead and pair a form-fitting slip—a big silhouette in the ’90s—with equally revealing heeled sandals. To tone down the look that helped popularize the “naked dress” trend, top it off with a sweeping trench coat.
The Frankie Shop Veyron Double-Breasted Trench Coat
Stuart Weitzman Nudist II 75 Sandal
Freja New York Caroline Bag Black
Statement Suit
This Tom Ford-era Gucci velvet suit was so good, Paltrow wore it twice: first to the 1996 VMAs, then again to Alessandro Michele’s Gucci show in 2021. Lean into velvet, one of the defining fabrics of the ’90s, or a similarly plush fabric, and balance the richness with a simple collared shirt (here, the blue contrast makes the look feel especially fresh). Finish the look with full-coverage pumps.
Ba&sh Boop Jacket
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Gap Oxford Big Shirt
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Ba&sh Babilon Pants
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Evening Shirting
Menswear-inspired shirting was a hallmark of ’90s fashion. Especially in evening wear, women reimagined the classic white button-down in elegant, unexpected ways, with everyone from Bessette Kennedy to Diane Keaton and, as seen here, Sharon Stone pairing the humble staple with sweeping skirts. (On the designer side, Carolina Herrera made the look a brand signature.) For a dressy night-out outfit, pair a sharply tailored white shirt with a maxi skirt. Barely-there sandals and distinctive jewelry will keep the outfit feeling modern and anything but matronly.
TWP My Newest Mistake Button-Up
Rick Owens Edfu Asymmetric Maxi Skirt
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Schutz Taliah Sandal Heels
Lié Studio Vera Knot Tie Earrings
Leopard Print
Leopard print was one of the era’s boldest fashion trends, bringing glamour, attitude, and excess to ’90s wardrobes (and it remains a prominent look today). Whether donned as a slip dress, an accessory, or a coat, as seen here on Halle Berry, it offers a bold counterpoint to the decade’s minimalist staples. Give a simple turtleneck-and-jeans formula more edge by throwing on an oversized coat in the animal print. The longer jacket hemline brings the drama, while the sharp boots add a fashion-forward finish.
Madewell Ruched Mockneck
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Rixo Jacoba Jacquard Coat
Levi’s Wedgie High-Waist Straight-Leg Jeans
Vagabond Shoemakers Fay Ankle Bootie
Collarless Blazer
Carrie Bradshaw aside, no fictional character defined ’90s fashion quite like Rachel Green on Friends. Jennifer Aniston, who played the style-savvy buyer and merchandiser, was just as admired off-screen, often stepping out in slip dresses, silky skirts, and other staples of the time. For a modern take, we’re partial to this collarless blazer silhouette, which has reemerged as a favorite in recent seasons, too. Pair it with draped trousers, a quirky pouch bag, and a quintessentially ’90s finishing touch: flip-flops.
Reformation Aphrodite Pleated Pouch
Leset Arielle Pocket Pant
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