Bootcut leggings can appear odd when paired with the wrong footwear, but these five styles are chic choices.

      Even mentioning the word leggings brings forth a flood of thoughts about whether this casual pant style is suitable or not. Regardless of your own feelings on the matter, it’s undeniable that leggings are definitely trendy. This season, one of the most prominent leggings trends making a comeback is bootcut leggings.

      Having grown up in the early 2000s, I feel a bit hesitant about the return of this shape, as I recall how notoriously difficult they were to style when they were previously in vogue. Our fashion preferences have certainly changed since the days of velour fabrics and low-rise styles, which means pairing them with dependable staples like chunky shearling boots feels almost out of reach.

      It's almost instinctual to think that bootcut leggings should be worn with those types of boots since it's in the name. However, confining ourselves to these flashy Y2K-inspired styling elements seems somewhat unoriginal and minimizes the versatility bootcut leggings actually offer. So, what footwear works best with bootcut leggings? Luckily, we can look to stylish dressers and celebrities for inspiration.

      From fashion-forward individuals heading to Pilates classes in these slightly flared silhouettes to more upscale variations crafted from structured fabrics that lend themselves to elevated footwear choices, there's definitely an art to creating a refined outfit—and it largely hinges on your choice of shoes. Given that bootcut leggings appear to maintain their popularity, it's essential to get acquainted with these key styles. Whether you're looking to refresh the silhouette or are simply curious about which contemporary shoes pair best with this cut, keep reading for the best footwear to wear with bootcut leggings this season and beyond.

      **5 Shoes to Pair With Bootcut Leggings in 2025**

      1. **Heeled Boots**

       Style Notes: It's obvious that boots and bootcut leggings complement each other perfectly. This shoe style is literally what the leggings are named after. For the trend to truly shine, it’s best to avoid overly sporty styles of leggings and opt for something with more structure, like a jersey or wool blend, which enhances the sophistication of heeled boots, as showcased by Parisian style icon Sabina Socol.

       Shop the Shoes:

       - **MANGO**: Block Ankle Boots With Square Toe - Block heels can sometimes appear dated, but when paired with another slightly divisive trend, they create a more premium look.

       - **ZARA**: Soft Leather Stiletto Heel Ankle Boots - A sharp heel combined with a square toe results in an elegant pairing.

       - **Khaite**: Nevada Patent-Trimmed Leather Ankle Boots - If budget were no concern, Khaite's Nevada boots, featuring a contrasting patent toe, would top my wishlist.

      2. **Lace-Up Flats**

       Style Notes: Given the tapered silhouette of bootcut leggings that gradually flares at the ankle, achieving a refined proportion is essential. Look for shoes that are low-profile with a hint of stiffness to harmonize with the sleek lines. Consider styles like ghillies, brogues, or the currently trendy Derby shoes.

       Shop the Shoes:

       - **CELINE**: Lise Perforated Triomphe Richelieu in Lambskin - Thanks to Celine's artistic director Michael Rider, Derby shoes are back on-trend.

       - **LeMarie**: Black Souris Flat Classic Derbys - Another desirable French option.

       - **MANGO**: Lace-Up Leather Ankle Boots - This ankle-height style from Mango nicely reinforces the "boot" in bootcut leggings.

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

      3. **Trainers**

       Style Notes: Although it's an obvious choice, trainers deserve a mention. These shoes naturally suit any type of leggings due to their athletic roots. Their universal appeal makes them the most adaptable option on this list, as virtually any trainer pairs well with this silhouette.

       Shop the Shoes:

       - **Asics**: GEL-KAYANO 14 Rubber and Metallic Mesh Sneakers - Asics has quickly risen as the trendy sneaker of choice.

       - **Adidas**: Japan W Leather-Trimmed Calf Hair Sneakers - A more stylish alternative to Sambas.

       - **Dries Van Noten**: Leather Sneakers - Arguably the season's top designer trainer.

       - **COS**: Minimal Leather Trainers - The textured finish adds a special touch.

      4. **Slippers**

       Style Notes: Wearing leggings emphasizes comfort, so why not fully embrace that with a pair of slippers? Slippers have transcended traditional housewear, with luxury brands like The Row pushing this cozy item into the outdoor realm. Now is the perfect time to try this trend with bootcut leggings, as their shape pairs well with a softer shoe choice.

       Shop the Shoes:

       - Gucci: Platform Slide Sandal - Ideal for both Majorca beaches and Chelsea streets.

       - THE ROW: Hugh Suede Slides - Lux