Straight-Leg Jeans and '90s Boots Emerge as Spring Trend

The classic minimalist look is making a comeback on the streets and runways.

Published on Feb. 25, 2026

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Fashion experts are noting a resurgence of the straight-leg jeans and blocky-heeled boot combo, a look popularized by '90s icons like Cindy Crawford, Winona Ryder, and Jennifer Aniston. This timeless pairing is being spotted on street-style stars and models during New York Fashion Week, as well as featured prominently on recent runways embracing '90s minimalism.

Why it matters

The return of this effortlessly chic '90s staple signals a broader trend towards more pared-down, classic silhouettes in fashion. As the industry shifts away from overly-trendy looks, the straight-leg and boot combo offers a versatile, timeless option that can be dressed up or down.

The details

Vogue fashion writer Olivia Allen is a fan of the look, citing its ability to avoid looking too costume-y or sporty. The walkable heel of the boots also helps address height insecurities while still maintaining a stylish, minimalist aesthetic. Designers like Khaite are embracing the '90s-inspired silhouettes on their recent runways, further cementing the trend's momentum.

  • New York Fashion Week is currently underway, where the straight-leg and boot combo has been spotted on numerous street-style stars and models.
  • Khaite's Autumn/Winter 2026 runway show featured the minimalist look prominently.

The players

Cindy Crawford

Iconic '90s supermodel who helped popularize the straight-leg jeans and blocky boot look.

Winona Ryder

Actress known for her minimalist '90s style, including the straight-leg and boot combo.

Jennifer Aniston

Actress whose off-duty looks in the '90s often included the straight-leg and boot pairing.

Olivia Allen

Vogue fashion writer who regularly wears the straight-leg and boot look to the office.

Khaite

Fashion brand that featured the minimalist '90s-inspired silhouettes prominently in their Autumn/Winter 2026 runway show.

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What they’re saying

“I have way too many pairs of jeans and find myself reaching for one of countless identical options in the morning. However, I am also, a) wary of falling into the trap of looking like a Bruce Springsteen tribute act and, b) allergic to trainers. The walkable heel helps me avoid both, while also addressing any height-based insecurities. There is no greater serotonin boost than strutting down the street in a pair of boots (plus sunglasses and wired headphones).”

— Olivia Allen, Vogue Fashion Writer (Vogue)

What’s next

As the weather continues to warm, fashion enthusiasts will be closely watching to see if the straight-leg and boot combo maintains its momentum as a key spring trend.

The takeaway

The return of this classic '90s look signals a broader shift in fashion towards more timeless, minimalist silhouettes that offer versatility and effortless style. For those seeking a chic, failsafe outfit option, the straight-leg jeans and blocky boots combo is a trend worth embracing this spring.