If you love the comfort of leggings but still want to appear polished, you're certainly not alone. For several seasons now, leggings have transitioned from being purely gym wear to a fashionable staple, expertly paired with an array of boots, ranging from ankle boots to knee-high options. While this legging-and-boot outfit combination might evoke memories of the 2014 celebrity style, it has made an unexpected resurgence. A prime example is Katie Holmes’ recent ensemble.
On Saturday in New York City, Holmes was seen walking around wearing none other than a pair of black leggings and brown ankle boots. In contrast to the dated combination of leggings with a short jacket and an infinity scarf, Holmes opted for a fresh approach. She grounded her look with a classic white tee, an elevated plaid trench coat, and a tan leather tote bag. What truly elevated her outfit was the balance created by the oversize trench, providing harmony with the fitted leggings, while the brown leather ankle boots introduced a chic and modern flair.
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 Teigen, who was seen in late August in Los Angeles rocking black leggings complemented by heeled ankle boots. Though the heels were a bold choice, Teigen balanced the look with an oversize striped button-down shirt layered over a white cropped tank, evoking a relaxed yet sophisticated vibe that aligns perfectly with the preppy-chic fashion trend.
Now that Holmes is embracing this trend, I’m certain we’ll see it expanding beyond just L.A. and NYC. To stay ahead of the game, scroll down and shop some of the best leggings and ankle boots.
Shop the best ankle boots and leggings:
Order multiple pairs of these leggings. Just trust me.
I love how these brown boots have a hint of burgundy to them.
There's a reason these are a top seller every year.
This pair may not technically be ankle boots, but they will definitely look good with leggings.
Style these with sock boots.
These look designer, but without the hefty price tag.
Suddenly it seems like all fashion people are wearing stirrup leggings.
Moto boots are back, and I'm here for it.
The neoprene automatically elevates an otherwise casual bottom.
I can't decide whether I love the brown suede material more or the unique loafer-boot hybrid design.
These affordable leggings are available in one-, two-, and three-packs.
The wide-ankle design is perfect for pairing with tight-fitting pants like leggings.
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