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 Replica Handbags , 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.
-
Found: The Perfect Finishing Touch To Your Elegant and Sophisticated Fall OutfitsHint: It's not a handbag.
-
Sure, Trousers Are a Fall Staple, But IMO, Dresses Are So Much Better—33 Gorgeous Styles From Mango, Reformation, and AnthropologieAn underrated essential.
-
The Fall Issue: Your Guide to What Matters in Fashion and Beauty Right NowFeaturing an interview with Jodie Turner-Smith, a spring shopping trend guide, beauty features, and more.
-
All of My Friends and I Shop at Shopbop—These 33 New Fall Items Are the StandoutsGorgeous knits, cool sneakers, chic jackets, and more.
-
The Fall 2025 Shopping Guide: Where to Buy the Biggest Trends of the SeasonYour short list of the season's key buys.
-
Not Classic Ballet Flats, Not Loafers—Everyone With Cool Style Will Be Wearing These Shoes With Black Trousers in Fall 2025As seen on Katie Holmes.
-
I Just Started Investing—31 Chic Pieces That Will Have Me Dressing the PartEffortless and elevated is the goal.
-
Summer or Fall, This Is the Casual But Elegant Flat-Shoe Trend That Always Looks Good With JeansAs seen on Jennifer Aniston.
