If you love the comfort of leggings yet 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 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.
(Image credit: The Image Direct)
On Katie Holmes: Khaite Amelia Bag ($2400); Chloé boots
Beyond Holmes, other trendsetting celebrities have recently embraced the legging-and-boot 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
Trust me: Order multiple pairs of these leggings.
I love how these brown boots have a hint of burgundy to them.
There's a reason why these are a top seller every year.
Matisse
Vegan Freeway Moto Boots
This pair may not technically be an ankle boot, but they definitely will look good with leggings.
Wardrobe.nyc
Side Zip Legging
madewell
The Idris Ankle Boots
These look designer, but without the hefty price tag.
Lna
Miles Stirrup Leggings
Frye
Olivia Harness Short
Moto boots are back, and I'm here for it.
Shopbop
Commando Neoprene Leggings
The neoprene automatically elevates an otherwise casual bottom.
Massimo Dutti
Track Sole Ankle Boots With Penny Strap
I can't decide whether I love the brown suede material more or the unique loafer-boot hybrid design.
Time and Tru
High-Rise Ankle Knit Leggings
These affordable leggings are available in one, two, and three-packs.
ZARA
Low Heel Ankle Boots
The wide-ankle design is perfect for pairing with tight-fitting pants like leggings.
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