10 ’90s-Inspired Outfits to Inspire Your Fall Wardrobe

The 1990s – an era of iconic supermodels, minimalist aesthetics, and a grunge-fueled cultural revolution. It’s no surprise that fashion lovers continue to be enthralled by the style of that decade, and Vogue, with its new six-part documentary series, *In Vogue: The 90s,* is celebrating the era’s fashion influence in a big way.

Inspired by the documentary and its star-studded cast, including Gwyneth Paltrow, Naomi Campbell, Victoria Beckham, and Kate Moss, we’ve curated 10 ’90s-inspired outfits that capture the spirit of the era. From effortlessly chic minimalism to edgy grunge and everything in between, these looks showcase the season’s hottest trends while celebrating the decade’s enduring style.

Minimalist Dressing, the Carolyn Bessette-Kennedy Way

Few figures embody ’90s minimalist style quite like Carolyn Bessette-Kennedy. Her iconic looks – luxurious leather tailoring, flattering A-line skirts, minimalist handbags, and signature tortoiseshell headbands – continue to inspire. For Fall 2024, recreate her effortless elegance with pieces from Mango, Toteme, The Row, and Banana Republic.

We’ll Always Have Teen Spirit With a Flannel Shirt

While minimalism reigned, grunge was another powerful force in ’90s fashion. Nirvana, Pearl Jam, and Sonic Youth fueled the trend, and the worn-in flannel shirt became a symbol of the movement. For Fall 2024, style it with Proenza Schouler’s tie-dye jeans, Everlane’s red-hot ballet flats, and Khaite’s python-print shoulder bag. Add a touch of ’90s cool with a cord necklace and silver cat-eye sunnies.

The ’90s Skirt Memo: Legs for Days

Before skirts embraced the longer, more ladylike silhouette, they were mini and as daring as ever. Naomi Campbell and Kate Moss were early adopters of this trend, and Sabato De Sarno at Gucci has taken notice for Fall 2024. Gucci’s buttery yellow leather mini is the perfect pairing for Madewell’s oversized blazer. Complete the look with Theory’s cropped cashmere sweater, a pair of knee-high boots from Staud, and Toteme’s leather shoulder bag.

A Touch of Sheer Transcends Time

Kate Moss’s iconic 1993 sheer dress moment outside the Elite model agency party is forever etched in fashion history. While not entirely sheer, Third Form’s slip dress offers a touch of sexy. Style it for your 9-to-5 with H&M’s sweeping wool overcoat, a pair of kitten-heel pumps from COS, and Coach’s covetable top-handle bag.

An Oversized Bomber Jacket Is a ’90s Model-Off-Duty Must-Have

From the ’90s to now, oversized leather bomber jackets add a touch of cool to any look. Banana Republic’s under-$1,000 option is a luxurious choice, pairing beautifully with crisp button-ups to straight-leg denim – another ’90s style signature. Finish the look with Havaianas’s square-toe flip-flops, a favorite of Carolyn Bessette-Kennedy and a timeless transitional shoe.

Edgy but Elegant Is the Name of This ’90s Game

Step into Fall with this edgy yet elegant ’90s-inspired look. Start with Prada’s funnel-neck leather jacket, a standout from the Fall/Winter 2024 runway, layered over Faithfull’s slinky, lace-trim slip dress. Ganni’s moto boots add a touch of grunge, while accessories from Alaïa and Sophie Buhai bring the cool factor.

Go Sporty Spice With a Zip-Up, Retro Sneakers, and a Wide Headband

Sporty style has transcended the confines of athleisure. Victoria Beckham’s jersey zip-up sweater, a pair of retro sneakers from Mango, and Lelet’s thick black headband are the perfect pieces for an elevated athletic look. This trend harks back to the ’90s, when icons like Sporty Spice and Mary J. Blige embraced the sporty look. Add a Saint Laurent leopard-print tote and yellow-tinted sunnies from COS for a touch of extra flair.

Ladylike Dressing: Then and Now

A-line skirts, lady jackets, and chic day clutches are key pieces for Fall’s ladylike-dressing trend. Embrace a ’90s twist with Toteme’s collarless jacket, Ferragamo’s micromini, and red-hot strappy sandals from The Row. This look is straight out of supermodel Claudia Schiffer’s playbook.

Slouchy and Undone, With a High-Fashion Touch

While a Hole reunion might be wishful thinking, you can still dress for the occasion. JW Anderson’s slouchy, tie-detail sweater requires minimal effort. Combine it with Frank & Eileen’s oversized flannel and a pair of casual corduroys for a cool, relaxed, and fashion-forward look. Add Tory Burch’s studded flats and Khaite’s tote for an edgy touch.

Before Goop, It Was ’90s Gwyneth Paltrow

Let Khaite’s burgundy leather maxiskirt take center stage, styled with Guest in Residence’s lightweight cashmere crewneck and Zara’s timeless khaki trench coat. Add tasseled leather loafers from Weejuns for a touch of prep, and Madewell’s soft suede tote for a modern twist. Finish with tortoiseshell sunnies, a nod to the ’90s style that started it all.

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