Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish.

Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish.

      Simply saying the word "leggings" invites a flood of considerations regarding the appropriateness of this casual trouser style. However, regardless of personal views, it's undeniable that leggings are currently in vogue. This season, a notable trend making a comeback is bootcut leggings. Having grown up in the early 2000s, I find the resurgence of this shape somewhat disconcerting due to my recollections of how challenging they were to style when they were trendy. Our fashion sensibilities have definitely shifted since the days of velour fabrics and low-rise cuts, making pairing them with classic staples like chunky shearling boots seem nearly impossible.

      It might seem only natural to style bootcut leggings with these types of boots, but confining ourselves to these flashy Y2K-inspired aesthetics feels limiting and does not capture the full range of versatility that bootcut leggings offer. So, what types of footwear pair best with bootcut leggings? Thankfully, we can look to stylish influencers and celebrities for inspiration.

      From trendsetters heading to Pilates classes in these slightly flared styles to more sophisticated adaptations in structured fabrics that allow for elevated shoe options, there is indeed an art to creating a polished outfit that heavily relies on the choice of footwear.

      As bootcut leggings show no signs of fading away, it’s essential to familiarize yourself with these key styles. Whether you're looking to revisit this silhouette or are simply curious about which contemporary shoes work best with it, check out the following list of the top shoes to wear with bootcut leggings this season and beyond.

      ### 5 Shoes to Wear With Bootcut Leggings in 2025

      1. **Heeled Boots**

       - **Style Notes:** It goes without saying that boots and bootcut leggings create an ideal pairing, as the name suggests. To achieve the trend's optimal look, it's wise to avoid overly sporty leggings and instead opt for those made from sturdier fabrics, like jersey or wool blends, which enhance the elegance of heeled boots, as illustrated by Parisian style icon Sabina Socol.

       - **Shop the Shoes:**

       - **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 Notes:** When wearing bootcut leggings, achieving a refined silhouette is crucial. Therefore, choose footwear that is low-profile yet provides some structure to complement the sleek lines. Consider styles like ghillies, brogues, or trendy Derby shoes.

       - **Shop the Shoes:**

       - **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 Notes:** Trainers may be the most obvious choice for leggings, given the athletic vibe of both the shoes and the bottoms. Their versatility makes them an adaptable selection that works with nearly any trainer.

       - **Shop the Shoes:**

       - **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 Notes:** Wearing leggings emphasizes comfort, so fully embrace this idea by choosing slippers. Slippers have evolved beyond home footwear, with luxury brands like The Row advocating for their wear outdoors. Now is the perfect time to experiment with this trend alongside bootcut leggings, as the soft silhouette pairs well with a more relaxed shoe choice.

       - **Shop the Shoes:**

       - **Gucci**: Platform Slide Sandal

       - **THE ROW**: Hugh Suede Slides

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

      5. **Flip-Flops**

       - **Style Notes:** While reminiscent of ensembles seen in "The O.C.," Kendall Jenner shows how to modernize this pairing for today. Sporting minimal leather flip-flops with a matching set while out in Paris, the model has revitalized this classic look.

       - **Shop the Shoes:**

       - **ARKET**: Leather Thong Sandals

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

      ### Why Trust Us

      At Who What Wear UK, fashion is our focus. Our editors, with years of industry experience, report on seasonal trends observed at international fashion weeks and collaborate with prominent names in fashion. Every item we recommend is thoughtfully chosen based on current trends, quality, and practicality. We regularly

Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish. Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish.

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Bootcut leggings may appear odd with the wrong footwear, but these five styles can look stylish.

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