If You Wear Converse Sneakers This Fall, Pair Them With Cigarette Jeans Like ’90s Icons

All products featured on Glamour are independently selected by our editors. However, we may receive compensation from retailers and/or from purchases of products through these links.

Converse sneakers were a sensation during the ‘90s. Leaving the sports world behind, they began to become the era’s most coveted footwear and became a fixture of the grunge aesthetic that emerged during the decade.

Their casualness and comfort were the characteristics that earned them a top spot in the fashion of the moment. Marc Jacobs was one of the designers who embraced them, presenting them in his Spring-Summer 1993 runway show for Perry Ellis. For the first time, streetwear had a grand stage to shine, showcasing Converse sneakers as the best way to complete a look without trying too hard.

Celebrities in the ‘90s were quick to adopt these sneakers as part of their casual, somewhat rebellious style, which denoted a significant cultural shift. Thus, the era’s trendy cigarette jeans became the inseparable partner of Converse sneakers. The pairing was seen on Drew Barrymore, who decided to add a touch of color with a red polka-dot blouse which looked effortlessly glamorous when combined with red lipstick and beachy blonde waves.

Drew Barrymore in Converse sneakers and cigarette jeans in the 90s.

Ron Galella/Getty Images.

And speaking of effortless ’90s outfits, we can’t leave out Gwyneth Paltrow. At the time, the actor’s style was defined by minimalist and distinguished pieces, whether she was on the red carpet or out with her then-boyfriend, Brad Pitt. On one of their dates, she wore a white shirt , black vest , leather jacket , and cigarette jeans—a look that is undoubtedly foundational for Hailey Bieber and Kendall Jenner, two lovers of timeless and versatile garments.

Gwyneth Paltrow in Converse sneakers and cigarette jeans in the 90s.

Getty Images

How to wear ’90s Converse sneakers and cigarette jeans in 2025The aesthetic power of Converse sneakers hasn’t diminished over time. On the contrary, they’re one of those always-on-trend pieces that have earned the title of “cult sneaker.” Whether you prefer the high-tops, low-tops, or new platform versions, the truth is they remain the best companions to cigarette jeans.

Converse Jack Purcell Sneakers

Converse sneakers and cigarette jeans with a t-shirt and blazer

Wearing cigarette jeans with Converse sneakers and a blazer creates a casual look that’s perfect for the office.

Edward Berthelot

The rules of fashion have changed, and Converse sneakers aren’t just suitable for completely relaxed looks. Now, adding a blazer to the mix makes them a great option to wear to the office, a casual Friday, or even a hearty lunch. Buttery yellow styles offer a pop of color without overwhelming the final look of a white T-shirt, washed-out blue cigarette jeans, and a skinny belt.

Converse Chuck Taylor All Star Sneakers

Converse sneakers and cigarette jeans with a short cardigan

Add a preppy touch to cigarette jeans and converse with a cropped cardigan.

Edward Berthelot

Also seen on Kaia Gerber.

Arnold Jerocki

Cigarette jeans can also be used to create preppy outfits, whether paired with a polo shirt or a crop top and short cardigan. While you can choose loafers to maintain the aesthetic, Converse canvas sneakers are recommended, not only for a change of pace, but also for constructing an outfit that greatly helps navigate the transition between seasons. The contrast is complemented by accessories like a hair ribbon, pearl necklaces, and a small bag.

Converse Chuck Taylor All Star High-Top Sneaker

Converse sneakers with cigarette jeans and a bodysuit

Grunge styles are the best option for wearing cigarette jeans and Converse sneakers.

Mila Gruber/Getty Images

’90s fashion lives on, not only through the minimalism showcased on the runways of fashion houses like Max Mara and Burberry, but also with the grunge aesthetic. This style is a favorite among fashionexperts, who haven’t hesitated to follow the teachings of Drew Barrymore and Gwyneth Paltrow by combining cigarette jeans with Converse sneakers, as well as a leather jacket and black bodysuit. Without a doubt, this look prioritizes comfort without neglecting style, just as it was done decades ago.

A version of this article was originally published by Vogue Mexico and Latin America.