3 min readCarolyn Bessette Kennedy’s ’90s outfits have been a source of inspiration for the season, but she wasn’t the only celebrity who defined the decade’s minimalist aesthetic. If you’re a fan of the looks you’ve seen in Love Story, the 10 well-dressed stars below deserve space on your spring mood board.
To help you channel Gwyneth Paltrow, Cindy Crawford, and others, we’ve recreated some of their best ’90s outfits using modern labels like Sézane, Reformation, Madewell, and Anine Bing. As a finishing touch, we’ve sprinkled in staple beauty products that ELLE editors still consider holy grails decades later.
Cindy Crawford
Cindy Crawford’s ’90s airport outfits helped define the supermodel-off-duty aesthetic of present-day style icons like Kendall Jenner and Hailey Bieber. The House of Style host wore a steady rotation of straight-leg jeans, leather jackets, and basic tees, tanks, and knits in a neutral palette. And similar to Bessette Kennedy, she wasn’t afraid to mix shades of brown with black.
Zara Suede Leather Jacket
Everlane RetroSoft Cotton Crew
Levi’s 501 ’90s Jeans
Banana Republic Boyfriend Cashmere Cardigan
Prada 55mm Rectangular Sunglasses
Halle Berry
Despite being one of the biggest movie stars of the decade, Halle Berry stuck to understated looks for most of her red carpet appearances. The white embroidered tank, black midi skirt, and strappy sandals she wore to the Lethal Weapon 4 premiere in 1998 still feel modern by today’s standards—but are perhaps better suited for dinner or date night than a formal event these days.
Rag & Bone Essential Rib Tank
Anine Bing Bar Silk Skirt
Jenny Bird Sundra Pendant Necklace
Carolyn Bessette Kennedy
If you’re going to borrow one styling trick from Bessette Kennedy this spring, make it her mixture of brown and black staples. Maintain a simple palette, and warm-weather essentials like collared shirts, linen pants, and loafers can be thrown together in a pinch.
The Shirt by Rochelle Behrens Jet Set Boyfriend Shirt
Tory Burch Classic Penny Loafer
Longchamp Large Le Pliage Panier Tote
Ray-Ban 58mm Irregular Oval Sunglasses
Kate Moss
Kate Moss was undoubtedly one of the decade’s biggest trendsetters—yet, off the runway, she defaulted to simple black crewneck sweaters and tees. For a Calvin Klein appearance in 1995, Moss styled the wardrobe staple with a white mini skirt and pointed-toe flats. Essie’s cult-favorite Ballet Slippers polish creates the barely-there manicure that supermodels still rely on today.
J.Crew Perfect Brushed Cashmere Crewneck
Skims Sheer Rib Long Sleeve Top
Favorite Daughter Favorite Skort
Essie Nail Lacquer in Ballet Slippers
Gwyneth Paltrow
Gwyneth Paltrow’s red carpet style makes an excellent reference for upcoming special-occasion looks. The understated white slip dress she donned for the 1995 Met Gala is noticeably similar to the minimalist wedding gown Bessette Kennedy wore the next year. And, for an updated take on Paltrow’s red-brown lip, try Clinique’s Almost Lipstick in Black Honey. Popular through the ’90s, the tinted balm is now one of TikTok’s favorite shades.
Norma Kamali Halter Drape Bias Gown
Vince Lightweight Cashmere Scarf
Reformation Skye Satin Mini Bag
Jimmy Choo Love Slingback Pump
Clinique Almost Lipstick in Black Honey
Winona Ryder
Winona Ryder’s style proves that a minimalist aesthetic can have grungy undertones. Throughout the ’90s, she embraced a dark, moody palette, often grounded by black leather and androgynous silhouettes. For her berry-tinted lip, try Revlon’s Rum Raisin lipstick, a decades-long favorite of celebrity makeup artists.
H&M Double-Breasted Blazer
Revlon Super Lustrous Lipstick in Rum Raisin
Janet Jackson
Janet Jackson also relied heavily on a rotation of menswear-inspired suiting. She often juxtaposed professional blazers and trousers with laid-back accessories like baseball caps and sneakers.
Theory Shrunken Three Button Blazer
Leau Classic Column Straight Trousers
Polo Ralph Lauren Classic Sports Cap
Keds Champion Platform Sneaker
Baby Gold 4mm Tube Hoop Earrings
Mariah Carey
Mariah Carey’s style is a testament to the power of a good LBD. Swap her flip-phone for an iPhone, and the chic pointelle tank dress she wore to the airport in 1999 feels just as current today—especially with mule sandals and slim sunglasses emerging as key accessory trends.
Cou Cou Pointelle Midi Slip
Jeffrey Campbell Agent Sandal
Miu Miu 54mm Irregular Sunglasses
Aurate Gold Ball Bracelet
Ana Luisa Small Bead Huggies
Julia Roberts
Julia Roberts, seen here in 1995, is a frequent source of inspiration for ELLE editors. Her fringed lob haircut, slouchy tailoring, and casual layers are worth revisiting—as is M.A.C’s Spice lip liner, one of the decade’s makeup-kit staples that still holds up today.
Saint Laurent 52mm Round Sunglasses
Gap Cotton Crochet Relaxed Sweater
Agolde Adine Shrunken Tee
Mac Cosmetics Lip Pencil in Spice
Jennifer Aniston
Navy V-neck pullovers are a key knitwear style for the season. Take notes from Jennifer Aniston and layer yours over a white crewneck tee and distressed denim—Kendall Jenner and other It girls are still wearing the same combo today.
Madewell 90s Crewneck T-Shirt
Jenni Kayne Flynn Cashmere Sweater
Citizens of Humanity Marlow Denim Cutoff Shorts
Tkees Platform Lily Sandal
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