3 Editors Recreate Iconic ‘90s Looks

This fall, we’re taking a trip back to the 1990s. From oversized baggy jeans to vegan leather pants and flannel overshirts, the key silhouettes of the decade are having a major style comeback — and we’re here to help you get the look.

GAP’s fall collection is filled with pieces that represent every type of fashion aesthetic from the decade, with grunge influences and nods to iconic supermodels alike. P.S. We recommend shopping the men’s section, too.

Inspired by this resurgence, we tapped editors Andrea Lavinthal, Jackie Fields and Hedy Phillips to share the nostalgic pieces from GAP they’re using to recreate their favorite ‘90s looks.

Hedy Phillips: Grunge Style

“I’m always rolling ‘90s silhouettes or trends into my style, whether it’s a chunky shoe, a choker or a crop top,” says Style Editor Hedy Phillips. This fall, she’s adding even more ‘90s influence to her wardrobe with the new GAP pieces that fit with her grunge aesthetic – starting with her favorite pairs of comfortable, loose-fitting jeans.

Phillips loves the innovative and grunge-chic Sky High Rise Wide Baggy Cargo Jeans with Washwell, which can easily be converted into shorts thanks to hidden zippers. “I love that GAP is playing with fits this fall, and that we’re finally back to baggy pants” she says.

For baggier styles, Phillips recommends trying the casual and comfortable 100% Organic Cotton '90s Loose Jeans with Washwell. “Don’t limit yourself to the women’s section,” she says. “To really nail that baggy look popularized in the ‘90s, check out the men’s section for an even looser fit.” She’ll pair her baggy jeans with GAP’s easy-to-style and versatile CashSoft Rib Sweater Vest for a uniquely ‘90s look that’s just as — if not more — trendy today than it was 25 years ago. “GAP has always been one of my go-to brands for reliable and stylish clothing that crosses both basics and trends,” she says.

“Crop tops like the Cropped Rib T-Shirt are a ‘90s style icon, and they have heavy rotation in my closet,” she adds. She’ll pair the top with the trendy Denim Midi Skirt with Washwell, another modern iteration on the popular ‘90s silhouette. “l love maxi skirts with tiny tops. It’s all about the hemlines.” To complete the look, Phillips will style the skirt with the GAP’s classic and comfortable vegan leather Moto Boots.

Shop pieces from GAP inspired by Hedy Phillips’ ‘90s style:

Sky High Rise Wide Baggy Cargo Jeans with Washwell, $89.95
100% Organic Cotton '90s Loose Jeans with Washwell, $79.95
Cropped Rib T-Shirt, $29.95
Moto Boots, $110
CashSoft Rib Sweater Vest, $49.95
Denim Midi Skirt with Washwell, $69.95

Andrea Lavinthal: ‘90s Minimalist Style

“I love how the style icons of the ‘90s interpreted minimalism in their own way while also looking classic and timeless,” says Style & Beauty Director Andrea Lavinthal. “Many of their best looks still hold up today.” With help from GAP, Lavinthal is channeling that energy this fall with her classic take on one of the decade's biggest trends.

“In the ‘90s, my high school version of the supermodel off-duty look was vintage jeans, a vest as a top and a black velvet choker,” she says. To get that it-girl look today, she’ll pair GAP’s chic yet casual CashSoft Puff Sleeve Sweater with a true ‘90s icon, vegan leather pants. Lavinthal loves the silhouette of the High Rise Faux-Leather Cheeky Straight Pants: “High-waisted and a straight leg will always be my go to.” For a different take on ‘90s style, she’ll try some of GAP’s classic baggy jeans (and like Phillips, might browse the men’s section for their even baggier styles from time to time) or the brand’s ankle-length Satin Tiered Maxi Skirt, which has a comfortable and relaxed fit.

To finish the look, Lavinthal loves the chunky black Faux-Leather Clogs, yet another nod to the trends of the decade. “GAP has the perfect mix of wardrobe essentials that I wear over and over, plus ‘I have to have this!’ finds like the clogs,” she explains, noting that much of the ‘90s minimalist look is about pairing those essential pieces with cool accessories. Lavinthal’s other favorite accessories from GAP’s new collection, like the Long Sherpa Coat and the Leather Belt Bag, make it possible to add subtle ‘90s touches to any outfit.

Shop pieces from GAP inspired by Andrea Lavinthal’s ‘90s style:

Satin Tiered Maxi Skirt, $69.95
High Rise Faux-Leather Cheeky Straight Pants, $89.95
CashSoft Puff Sleeve Sweater, $49.95
Faux-Leather Clogs, $69.95
Long Sherpa Coat, $148
Leather Belt Bag, $98.98

Jackie Fields: Oversized-Chic Style

For Deputy Beauty Director Jackie Fields, the ‘90s were all about layers. “Music videos had a big influence on me, so loving flannel, baggy jeans and oversized jackets was inevitable,” she says. “These days, I can appreciate varying silhouettes.” Despite her evolving style, choosing from GAP’s collection of layers and on-trend baggy jeans is a no-brainer for Fields as she brings a modern touch to her favorite oversized looks: “I love that GAP has amazing staples as well as interpretations on trends that complement the other items in my closet.”

Though Fields was too young to wear the iconic slip dress in the ‘90s, she did wear a lot of slip shirts that were covered by another staple: the cardigan. Fields loves the classic V-neck Pointelle Cardigan from GAP, especially when it’s paired with cargo pants or loose ‘90s jeans. Of course, she also likes the brand’s oversized button-down Flannel Big Shirt, a classic take on one of the decade's defining patterns.

Fields also turns to turtlenecks when she thinks of the styles and silhouettes of the ‘90s. She loves the CashSoft Turtleneck Mini Sweater Dress as a contemporary version of the classic chunky turtleneck sweater. Plus, it’s perfect for the fall to winter transition.

For accessories, Fields will be sporting GAP’s interpretations of even more of her favorite ‘90s looks. “I’m obsessed with GAP’s puffer outerwear,” she says of the quilted Faux-Leather Cropped Puffer Vest. “It’s so stylish. It hints at ‘90s fashion, but with modern elements that feel very elevated.” She’ll add even more nostalgia to her fall wardrobe with the single-strap Faye Platform Heels in black.