Leggings are comfortable, versatile, and easy to style — and the right boots can make the whole outfit pop. Whether you’re going for a casual, edgy, or functional look, here are 10 of the best boots to wear with leggings, including some solid picks from Bates for those who like durability with style.
1. Bates Women’s Tactical Sport 2 Mid DRYGuard+ Boot
These waterproof tactical boots from Bates bring a sporty edge to leggings. The mid-height design balances well with slim-fit leggings, and the DRYGuard+ protection makes them a smart choice for unpredictable weather.
• Best for: Utility style, rain or snow
• Why they work with leggings: Sleek profile with high function
2. Dr. Martens 1460 Smooth Leather Lace Up Boots
A classic that never goes out of style. The combat-boot look pairs effortlessly with leggings and an oversized sweater or leather jacket.
• Best for: Edgy, casual streetwear
• Why they work with leggings: The contrast of chunky soles and slim leggings creates balance
3. Bates Women’s GX-8 Side Zip Boot
These are great for those who want rugged, all-day comfort with a side of style. The side-zip makes them easy to slip on over leggings, and the breathable lining keeps things fresh.
• Best for: All-day wear, travel, active days
• Why they work with leggings: Functional without sacrificing silhouette
4. Sorel Joan of Arctic Wedge II Boots
These wedge boots give leggings a dressier vibe without going full heel. Great for fall and winter outfits, especially with long coats or chunky knits.
• Best for: Cold weather chic
• Why they work with leggings: Adds length and lift while staying comfy
5. Bates Women’s Maneuver Side Zip Boot
If you’re looking for something between classic tactical and everyday casual, these boots strike that balance. Rugged enough for the outdoors but sleek enough to pair with leggings and a utility jacket.
• Best for: Transitional seasons, everyday wear
• Why they work with leggings: Tapered fit at the ankle compliments leggings perfectly
6. Blundstone Original 510 Chelsea Boot
Chelsea boots are a go-to with leggings. The clean lines and easy slip-on design make them a staple for minimalist wardrobes.
• Best for: Simple, everyday style
• Why they work with leggings: Streamlined and timeless
7. Timberland Women’s Courmayeur Valley 6-Inch Boot
This boot adds a soft, feminine twist to the traditional Timberland ruggedness. Wear it with leggings and a flannel for a cozy, outdoorsy look.
• Best for: Fall layering, weekend outings
• Why they work with leggings: The suede and knit details add contrast to smooth leggings
8. UGG Classic Ultra Mini Boot
These low-profile boots from UGG are perfect for a cozy, laid-back vibe. Pair with fleece-lined leggings and a hoodie for the ultimate comfort outfit.
• Best for: Lounging, casual errands
• Why they work with leggings: Snug fit around the ankle looks great with slim leggings
9. Steve Madden Bettyy Lug Sole Bootie
With chunky soles and a slightly higher shaft, this bootie creates a stylish contrast with leggings. Great for a city look with attitude.
• Best for: Trendy streetwear
• Why they work with leggings: Adds height and edge to a basic outfit
10. Columbia Women’s Newton Ridge Plus Waterproof Amped Hiking Boot
Functional meets fashionable. These lightweight hiking boots from Columbia offer support and weather resistance, making them perfect for outdoor adventures in leggings.
• Best for: Hiking, outdoor walks, fall adventures
• Why they work with leggings: Clean design and supportive structure balance well with form-fitting leggings
Final Thoughts
Leggings are basically a blank canvas — and boots are the brush strokes. Whether you lean tactical, trendy, or timeless, the right pair can take your leggings look to the next level. And if you want something durable and functional, Bates boots are definitely worth considering.
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