Barrel-leg jeans continue to be in the spotlight. While undeniably trendy, they’re one of those denim styles that can be tricky to pull off. With their high rise, roomy thigh, and sharp taper at the ankle, finding the perfect shoe to wear with barrel jeans can feel like a high-stakes fashion equation.
Enter Hilary Duff. Our girl has been quietly leveling up her street style game since her Lizzie McGuire era, and her latest look delivers a master class in how to nail this silhouette. Spotted on a rainy day in L.A.—cue "Coming Clean"—Duff paired a dark-wash pair of barrel jeans with the chicest, most directional boots of the season: a square-toe heeled ankle boot.
Why does this work so well? It’s all about balance and proportion. The cropped or ankle-grazing hem of the barrel jean naturally cuts off the leg line, but a heeled boot, especially one that tucks right under the cuff, easily restores that length.
But the real genius is in the subtle details. Duff’s subtly square toe feels cooler than a traditional pointy tip. This slight angularity mirrors the curve and structure of the jeans themselves, creating a cohesive, fashion-forward look that avoids any awkward bulkiness at the ankle. She smartly paired it all with a chunky knit sweater—perfect for "winter" in Los Angeles—proving that sometimes, the most befuddling trends just need the right foundational pieces to become effortlessly chic. Keep scrolling to shop several pairs of barrel jeans and square-toed ankle boots so you can try Duff's styling trick this season for yourself.
Shop Barrel Jeans and Square-Toe Ankle Boots
This super-soft style features just a slight barrel for those dipping their toes into the trend for the first time.
It's important to balance wider proportions with fitted pieces, like tops and sleek shoes.
Free People was one of the first brands to really nail this trend — this style now comes in so many fun colors and patterns.
Another great baby barrel style to consider.
The look works with black jeans, too.
You know we had to include a pair of Levi's in the mix.
This glove-like ankle shaft is ideal for wearing with baggier styles of pants.
Not looking to add height? Opt for kitten heels instead.
Honestly shocked that these classic Staud beauties are still in stock.
A block-heel bootie does the trick too.
Note how the square toe is mirrored in the slim rectangular heel.
A square footbed and heel will most certainly keep 'em on their toes.