27 Chic Jeans and Boots for Fall and Winter 2025 Outfits

I know I am not the only one living in jeans and boots come cooler weather. The timeless combination is a go-to because of the endless styling options and the fact that the duo never goes out of style. Since the arrival of fall and winter 2025, I have made it a point to virtually set aside any jeans and boots that catch my eye—one of the many reasons for my zillion open tabs. More often than not, these tabs lead to standout finds from Zara, Madewell, and Nordstrom.

Below, I curated a quick list of my current jeans and boots favorites from each of the retailers that are guaranteed to come together to create a chic fall and winter outfit with the help of a great sweater and elevated outerwear. Included in the mix are trendy denim and boot styles like barrel silhouettes, kitten-heel boots, cuffed jeans, suede booties, and dark-wash pieces. You’ll also find classic straight-legs and Chelsea ankle boots.

Keep scrolling to shop standout 27 picks that will lead to chic jeans-and-boots outfits. So many of these are even discounted thanks to on-going 2025 Cyber Week sales.

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