Stylish and rugged—chukka boots are one of the best footwear options for men. Few other options can rival the versatility of chukkas. They can be paired equally well with jeans and a t-shirt as ...

We turned to street style stars for a little bit of extra inspiration for wearing jeans with ankle boots. And there's not only a look for every style point of view, but also for every time of day.

Below, I'm highlighting the 32 best winter boots to wear with jeans, from leather riding boots to chocolate ankle boots and chic suede options. Tony Bianco. Quincy Boots.

"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links." Regardless of the season, ankle boots are an essential wardrobe item. In spring, you can find celebs ...

How to style brown boots with jeans for summer and fall 2025, according to “Glamour” editors. See their styling tips here.

When I ask, how do I wear boots with jeans, their answer is simple. Put on the jeans one leg at a time, then put your feet in the boots. It’s not that simple for women.

Diana, Princess of Wales, favored cowboy boots with jeans and a blazer. Credit... Tim Graham Photo Library, via Getty Images. By Vanessa Friedman. Oct. 16, 2023.

So you want to wear some ankle boots with jeans, eh? But not quite sure exactly how to do it while looking stylish? We got you! Skip to main content. 24/7 Help. For premium support ...