Bootcut leggings can appear odd with unsuitable footwear, but these five styles are stylish.

      Merely mentioning the term leggings prompts a flood of thoughts about their appropriateness as a casual trouser option. Regardless of personal views on them, it’s clear that they are quite trendy. This season, however, one of the notable trends in leggings is the resurgence of bootcut styles. Although I grew up in the early 2000s, I find the return of this shape somewhat off-putting due to the challenges I remember in styling them when they were actually fashionable. Our preferences have certainly shifted since the era of velour fabrics and extremely low-rise styles, making it seem almost improbable to pair them with reliable footwear like chunky shearling boots.

      It might feel instinctive to think that bootcut leggings should be styled with such boots, as implied by the name. However, confining ourselves to vintage Y2K-style combinations can feel repetitive and narrow, considering the true versatility of bootcut leggings. So, which shoes pair best with bootcut leggings? Luckily, we can draw inspiration from chic fashion icons and celebrities. From influencers heading to Pilates in slightly flared designs to more refined looks featuring bootcut leggings made from structured materials that suit a more elevated shoe choice, there’s certainly an art to creating a polished outfit, heavily influenced by footwear.

      Since bootcut leggings show no signs of fading from fashion, it's essential to familiarize yourself with these primary styles. Whether you're looking to resurrect this silhouette or are simply curious about the best modern footwear options to complement it, continue scrolling for the most suitable shoes to wear with bootcut leggings this season and in the future.

      5 Footwear Options for Bootcut Leggings in 2025

      1. Heeled Boots

      **Style Insights:** It goes without saying that boots and bootcut leggings complement each other perfectly, giving the leggings their name. For this combination to shine, it's best to avoid overly sporty leggings and opt for styles that offer more structure, like those made from jersey or wool, to enhance the sophistication of heeled boots, as shown by Parisian It girl Sabina Socol.

      **Shop the Footwear:**

      - **MANGO** - Block Ankle Boots With Square Toe

      - **ZARA** - Soft Leather Stiletto Heel Ankle Boots

      - **Khaite** - Nevada Patent-Trimmed Leather Ankle Boots

      2. Lace-Up Flats

      **Style Insights:** Achieving a refined silhouette is crucial when wearing bootcut leggings, characterized by a tapered fit through the leg that gradually widens at the ankle. Choose footwear that is low-profile yet slightly stiff to balance the clean lines. Options include ghillies, brogues, or trendy Derby shoes.

      **Shop the Footwear:**

      - **CELINE** - Lise Perforated Triomphe Richelieu in Lambskin

      - **LeMarie** - Black Souris Flat Classic Derbys

      - **MANGO** - Lace-Up Leather Ankle Boots

      - **COS** - Chunky Lace-Up Leather Mary-Jane Shoes

      3. Trainers

      **Style Insights:** While it may be obvious, it's worth mentioning that trainers are a go-to option for any type of leggings due to the inherent athletic associations with both. Their versatility makes them the most adaptable choice on this list, as almost any trainer will complement this style.

      **Shop the Footwear:**

      - **Asics** - GEL-KAYANO 14 Rubber and Metallic Mesh Sneakers

      - **Adidas** - Japan W Leather-Trimmed Calf Hair Sneakers

      - **Dries Van Noten** - Leather Sneakers

      - **COS** - Minimal Leather Trainers

      4. Slippers

      **Style Insights:** Wearing leggings emphasizes comfort, so why not fully indulge with a pair of slippers? As I’ve mentioned before, slippers are now acceptable as outdoor footwear, with luxury brands like The Row championing this cozy item for outdoor use. If you're going to try this trend, doing so with bootcut leggings is perfect, as the softer shoe choice balances the more structured outline of the leggings.

      **Shop the Footwear:**

      - **Gucci** - Platform Slide Sandal

      - **THE ROW** - Hugh Suede Slides

      - **M&S** - Borg Back Tab Mule Slippers

      5. Flip-Flops

      **Style Insights:** Though reminiscent of on-screen looks from The O.C., trendsetter Kendall Jenner has refreshed this pairing for the modern age. Seen out in Paris, she styled this outfit with minimal leather flip-flops, a latte-hued matching set, and a mocha-colored suede bag. As the French say, très chic.

      **Shop the Footwear:**

      - **ARKET** - Leather Thong Sandals

      - **Proenza Schouler** - Cable Leather Flip Flops

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