Hilary Duff has discovered the most stylish boot trend to wear with barrel jeans.

      Barrel-leg jeans remain in the spotlight. Although they are undeniably fashionable, they can be one of those denim styles that are difficult to style. With their high rise, spacious thigh, and sharp taper at the ankle, choosing the right shoe to wear with barrel jeans can feel like a challenging fashion puzzle. Enter Hilary Duff. Since her days on Lizzie McGuire, she has been gradually enhancing her street style, and her latest outfit demonstrates how to master this silhouette. Seen on a rainy day in L.A.—cue "Coming Clean"—Duff paired dark-wash barrel jeans with the most stylish, trendsetting boots of the season: a square-toe heeled ankle boot.

      Why does this combination work so effectively? It’s all about achieving balance and proportion. The cropped or ankle-length hem of the barrel jean naturally shortens the leg line, but a heeled boot, particularly one that fits snugly beneath the cuff, easily restores that length.

      However, the true brilliance lies in the subtle details. Duff’s slightly square toes feel trendier than a conventional pointed toe. This slight angularity reflects the curves and structure of the jeans themselves, forging a harmonized, fashion-forward appearance that sidesteps any awkward bulk at the ankle. She wisely styled it with a chunky knit sweater—perfect for a "winter" day in Los Angeles—showing that even the most puzzling trends can achieve effortless chicness with the right foundational pieces. Keep scrolling to explore various pairs of barrel jeans and square-toed ankle boots, so you can replicate Duff's styling trick this season yourself.

      (Image credit: Backgrid) Shop Barrel Jeans and Square-Toe Ankle Boots

      DL1961 Miro Barrel High Rise Jeans

      This incredibly soft style offers just a hint of barrel for those venturing into the trend for the first time.

      Veronica Beard Jean Leticia Barrel Leg Jeans

      Balancing wider proportions with fitted pieces, like tailored tops and sleek shoes, is essential.

      Free People Good Luck Mid Rise Barrel Jeans

      Free People was among the first brands to excel at this trend—this style is now available in many fun colors and patterns.

      AG Mercer High Waist Barrel Jeans

      Another excellent baby barrel style to think about.

      AllSaints Sadie Barrel Leg Jeans

      This style also works well with black jeans.

      Levi's Baggy Dad High Waist Barrel Leg Jeans

      Of course, we had to include a pair of Levi's in the selection.

      Reformation Remy Stretch Ankle Boots

      This glove-like ankle shaft is perfect for pairing with looser pant styles.

      ALOHAS Nash Kitten Heel Booties

      If you prefer not to add height, go for kitten heels instead.

      Staud Hendrix Ankle Boots

      I'm honestly surprised that these classic Staud beauties are still available.

      Steve Madden Pammy Block Heel Booties

      A block-heeled bootie also does the job well.

      Rag & Bone Avery Zip Boots

      Notice how the square toe is echoed in the slim rectangular heel.

      Jeffrey Campbell Chekmat Square Toe Booties

      A square footbed and heel will definitely keep them on their toes.