For many, the word most associated with ’90s style is “minimalism”. While structured white button-downs and Yohji Yamamoto skirt suits CBK certainly evoke the era, there was plenty more happening on the fashion front during the decade. Although not as freewheeling as the ’70s, a carefree ease made itself felt across the era’s style. This mood was distilled in the baggy trousers adored by the likes of Drew Barrymore and Winona Ryder back in the day.

Now, we’re seeing them make a return for autumn/winter 2026. How to style them this time around? Well, you could lift inspiration from the OG era, wearing them with matching tailoring or a casual leather jacket, but a pair of baggy trews are as versatile as they are amply cut – as easily paired with billowing boho blouses as with fitted tees. And that’s before we even get started on the potential footwear parings! Read on for our favourite ways to style this iconic ’90s throwback trouser shape for the season ahead.

Drew Barrymore in baggy pants in 1993.

Ron Galella/Getty Images.

Winona Ryder in baggy pants in 1991.

Ron Galella/Getty Images.

While bright pops of colour were all the rage in spring and summer, autumn’s arrival has us leaning towards moodier hues. Although, really, you can pull this off with more or less any monochrome tone – even pink or peach, as was seen on the runways at Chloé, Anna Sui and Chanel. For a quick and easy ’90s outfit formula, just slip on a black shirt, your baggiest tailored trousers and sling-back heels in a matching hue, and you’re good to go.

No longer a seasonal item, the boho blouse has become a perennial staple – and when you try pairing yours with a pair of pleated baggy trousers, you’ll see why. Together, they create a look that simultaneously exudes polish, ease and romance. The combo can also be dressed up or down – add a cardigan for a more cosy vibe or a long trench coat for a more dramatic impact. However you choose to style it, our go-to shoe for this look is a mid-heeled suede pump.

If ever you thought that baggy trousers couldn’t be elegant, think again. It’s all about the pairing, with carefully chosen accessories capable of doing some serious heavy lifting. Minimalist, plain leather loafers, for example, help make the relaxed vibe feel intentional – and all the more chic for it. Wear with a striped shirt – and perhaps even a long string of pearls and a slim belt to cinch the waist.

Skims Fits Everybody Long Sleeve Crew Neck Bodysuit

What do ’90s fashion icons like Jennifer Aniston, Cameron Diaz, Julia Roberts, and Sarah Jessica Parker all have in common? Their love for a heeled loafer, of course! A high-waisted baggy pant – another of the era’s style staples – makes for an intuitive option to build a look around. Style with a long-sleeved bodysuit.

Do you have a loud-and-proud blouse knocking about in your closet that you can’t figure out how to wear? Well, lucky for you, baggy trousers ground the eccentricity of, say, a billowing, printed pussy-bow shirt – especially when the colour palette is considered. Red with brown, white with blue, and green with khaki… you get the gist. Style with chunky-soled sneakers.

Plus Court Vintage White Sneaker

With the turning of the seasons upon us, there’s never been a better time to add a pair of loose-fitting corduroy trousers to your rotation. Offering comfort without sacrificing style, you can simply pair them with a white T-shirt – which you can dress up with a scarf, should you wish – and flat white trainers.