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.
-
This Is the Shorts Color Trend Everyone Is Starting to Wear Because Fall Starts Next MonthTime to transition the wardrobe.
-
"It Goes to Show Representation Does Still Matter": Luciane Buchanan on Powerful Chief of War RoleThe Night Agent star finds her next act in one of Hawaii's most prominent rulers.
-
Not All Designer Pieces Achieve It Status, But These 14 Luxury Finds Are Set to by FallSmart, long-term purchases.
-
If You Care About What Fall Sweater Trend It Girls Are Already Wearing, It's This '90s OneSpotted on Olivia Rodrigo in London.
-
Katie Holmes's Tip for Looking Rich? Lose the Flip-Flops and Wear These Classic Flats (in *This* Color) InsteadA shoe trend to take from summer to fall.
-
Bring On the Transitional Weather—29 Perfectly Chic Pieces FromReplica Store to Wear Straight Through FallEffortless dressing right this way.
-
7 Celeb Outfits That Prove You Can Look Stylish Even When It's SwelteringIf you're in a summer wardrobe rut, this is the inspiration you need.
-
This Shoe Color Trend Is Chicer Than Black, Burgundy, and BrownKaia Gerber agrees.
-
The Pretty Dress Trend L.A. It Girls Are Bringing Into Fall (and the "Basic" Style They Already Forgot About)It's finally time to part ways with boring linen dresses.
-
Experienced Shoppers Are Styling Cowboy Boots With This Specific Denim Trend to Make Them Look Less CostumeyTake a page out of Kendall Jenner's style book.
