Sorry, But '90s Celebs Did Autumn Dressing Better—7 Outfits With Jeans That Prove It

When you think of the '90s, what instantly comes to mind? It was a decade packed with pop culture moments that years later, we still can't seem to let go of. From the creation of "The Supers" (that special breed of super supermodels) to the dawning of hip-hop and grunge, the inception of Sex and the City and Friends… the list goes on. But above all the chaos, when I think of the era, I think of the golden age of denim.

Be it Calvin Klein’s now-iconic ads to Tommy Hilfiger dressing the music icons of the moment, many of the decade’s most memorable looks had one staple at the core: a pair of jeans. The overarching '90s aesthetic we tend to think of favoured clean lines, sleek silhouettes and a generally muted colour palette, so it makes sense that denim would rise in popularity.

Levi’s 501s, with their relaxed fit, hit the casual-cool sweet spot. The mid-rise, straight-leg silhouette in a perfectly faded, lived-in wash was a must-have for people everywhere. Today, fashion people (myself included!) still scour vintage stores and charity shops in search of that ever-elusive perfect pair, especially in the autumn, when our jeans can really shine.

Blue jeans were the uniform of the cool. I can think of so many examples: Tyra Banks in a double-denim get-up in The Fresh Prince of Bel Air, Carolyn Bessette-Kennedy's entire capsule wardrobe; not to mention Drew Barrymore, Jennifer Aniston and Gwyneth Paltrow, who played some of the decade's most iconic film and TV characters. The '90s were filled with celebrities who made jeans feel like more than just another trend, so it’s no surprise that modern denim brands like Agolde and Re/Done have looked to the era for inspiration, reimagining those timeless silhouettes for a new audience craving that same cool.

With a plethora of '90s trends back at the forefront, channelling the decade’s style has never been easier. For me, the best autumn jeans outfits all tap into that authentically cool, carefree minimalism the era did so well. So, if you’re keen to give your wardrobe a nostalgic injection but don’t fancy looking like Scary Spice (no offence, Mel B), scroll on for the seven best '90s autumn jeans outfits to re-create this season.

7 '90s Autumn Jeans Outfits to Re-Create This Season

1. Cindy Crawford: Blazer + Jumper + Jeans + Boots

Style Notes: I had to do a double take when I spotted Cindy Crawford in a '90s jeans ensemble that I know I've seen people wearing over the past few years, butter-yellow jumper and all. Wearing square-toe boots, a light-brown leather blazer and a soft pop of yellow via her jumper, she uses her jeans as the grounding base. It balances laid-back cool with a pulled-together edge, and is proof, if ever we needed it, that great denim styling never dates.

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2. Drew Barrymore: Blazer + Cargo Jeans + Loafers

Style Notes: Drew Barrymore might be admired today for her warm personality as a talk-show host, but back in the '90s, she was a total It girl, especially where her denim outfits were involved. Often embracing a relaxed, slightly undone aesthetic, her above outfit leans into the timelessness of minimalism. Her loose blazer paired with low-rise cargo jeans, well-worn loafers and oval sunglasses is a true reminder that an unfussy look will always be best.

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3. Whitney Houston: Hat + Blazer + Jeans + Converse

Style Notes: She may have made her mark on the era’s music, but Whitney Houston’s style was just as memorable off-stage. Spotted here returning from Miami, she wore a butter-yellow (I'm sensing a theme here) bowler hat, a loose-fitting blazer, straight-leg jeans and classic Chuck Taylor Converse; an outfit that will transition seamlessly into autumn 2025. In fact, it feels more relevant than many of the modern interpretations I’ve seen today— such is the beauty of '90s fashion.

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4. Gwyneth Paltrow: T-shirt + Jumper + Jeans + Leather Jacket

Style Notes: Gwyneth Paltrow may be best known these days for yoni eggs, but before she became the queen of health and wellness, she was an actress with a refined sense of style. Whilst on the set of The Devil’s Own, she was spotted in a look that still serves serious autumnal inspiration: relaxed denim, a crisp white tee, a soft-knit jumper and a classic leather jacket. It’s understated, timeless and oh-so '90s. Now all we need is '90s Brad Pitt, and we’re good to go.

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5. Jennifer Aniston: Sheer Top + Jeans + Sandals

Style Notes: Jennifer Aniston’s ’90s style is often labelled one of the most iconic of the decade, and rightly so. Whilst the chunky clogs and her namesake haircut (who could forget The Rachel) may have defined the era, it’s her fuss-free, laid-back approach to dressing that endures, reflected in the style of Kaia Gerber, Bella Hadid and Hailey Bieber. Take her sheer button-down shirt and jeans combo. It’s the ideal autumn outfit for those warmer days when you want to keep things light whilst still making a subtle statement.

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6. Winona Ryder: Graphic Tee + Leather Jacket + Jeans + Flat Boots

Style Notes: No '90s-jeans round-up would be complete without a nod to the Stranger Things actress. Well-versed in all things grungy and gothic, Winona Ryder's graphic tee, leather jacket and boot ensemble is primed to be copied by those who want a look with a touch of edge in 2025.

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7. Courtney Cox: Turtleneck + Jeans + Heeled Boots

Style Notes: If Courtney Cox’s portrayal of Monica in Friends didn’t already cement her as a ’90s style icon, her pared-back wardrobe certainly should. From slinky dresses to barely-there sandals, every look is a win, but nothing quite beats her mastery of jeans. The effortless cool of her simple jeans-and-jumper combos is exactly why designers keep looking back to the ’90s for inspiration. Take a leaf out of her book and strip it back to basics this season: a simple lightweight jumper, leather boots and a pair of light-wash denim for an easy look.

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