On Katie Holmes: Khaite Amelia Bag ($2400); Chloé boots Beyond Holmes, other trendsetting celebrities have recently embraced the leggings-and-boots pairing in a 2025-ready way. Take Chrissy ...

Pair your leggings with riding boots to elevate their look. This equestrian-inspired style exudes a timeless elegance that's hard to beat. While many fashion people opt for black leggings teamed ...

There’s an easy-to-remember rule when it comes to figuring out the right top to wear with ankle boots and leggings: high heels (3 inches and up) look better with a long shirt while low-heeled ...

For colder climates, though, there's only one solid choice of shoes to wear with leggings, and riding boots are it—period. Scroll down to shop the once-dated outfit combo going viral right now ...

Sydney Sweeney wore micro ruffle bloomers, a tan suede corset and tan cowboy boots to match as she attended the 2025 Stagecoach Festival. Sydney Sweeney is dressed like country music star once again.