Denim is Timeless, But This 90s Jeans Trend is Set to Take Over in 2027

I’ve always considered myself a bit of a denim connoisseur, and the kind of dresser whose capsule wardrobe is built around a pair of well-crafted jeans. Whether it’s fashion-forward pintucks or sleek stovepipes, I’ve flirted with just about every style going at one time or another, but out of all the trending types I’ve tried, I always come right back to the holy grail: ‘90s-style mid-rise, straight-leg jeans.

Plenty of denim trends have come and gone, but mid-rise, straight-leg jeans were an instant crowd-pleaser. With a relaxed fit through the hips but narrower down the thighs and legs, their clean lines and mid-blue wash make them ideal for everyday wear. They’re gloriously hardy, unfussy and unassuming, which is exactly why, to this day, they remain the ultimate pair of jeans in a stylish dresser’s denim rotation.

Think back to Princess Diana strolling across the polo pitch in an oversized black blazer, graphic sweatshirt and cowboy boots, or a baby-faced Kate Moss in her go-to off-duty ‘fits. And of course, the numerous times they were worn by Carolyn Bessette-Kennedy and Halle Berry; every It girl owned a pair, and the style was the focal point of chic pre-millennium style.

With the fashion cycle continuously drawing from bygone eras (lately, especially the ‘90s), a revival was long overdue. We first sensed the change earlier this year, when the buzz surrounding Love Story created a dressing-like-CBK hysteria. Almost overnight, fashion people were hunting down her signature ankle-grazing Levi’s, and attendees at Celine‘s spring/summer 2026 show sported the same style as part of a Canadian tuxedo. You’re more likely to spot Kendall Jenner or Hailey Bieber in a mid-blue, straight-leg pair of jeans than any other denim trend (Hailey even included a pair in her collaboration with Gap), proving just how much ’90s jeans have become a hot commodity.

And how are we wearing them now? Well, in much the same way as women did 30 years ago. Sharp wool coats, crew-necks and flat-soled boots are perfect for winter, or style things up with loafers and a glossy leather trench in the most ’90s way possible. Either way, the fashion set has made straight-leg denim their uniform this season. As we turn the corner into 2027, there’s never been a better time to invest in this enduring style—especially as you can get a pair in loads of versatile washes that all carry the same cool-girl energy. Ready to update your look with just one key buy this season? Scroll down to shop the best ’90-style jeans.

Shop the ’90s-Style Jeans Trend: