Born Binghamton Ankle Boots
This rugged style is seriously well-crafted: real, distressed suede gives them a lived-in, well-loved look, while a steel shank provides the ultimate in all-day support. Also available in three other colors.
To buy: $73; 6pm.com.
Aerosoles Tax Bracket Ankle Boots
Don’t let this pair’s super stylish looks fool you—while the sleek, pointed toe and edgy embellishments may be perfect for an evening out, those fashion-forward details conceal an extra-cushioned memory foam footbed, so you can dance the night away. Also available in grey.
To buy: $100; aerosoles.com.
Clarks Maypearl Edie Boots
These booties come in an unexpectedly cool color combo of olive suede and brown leather and are made with Clarks’s Ortholite technology, so they’re supportive, lightweight, and comfortable all at once. But the best part is their extra low profile, which won’t cut your legs off at the ankles (just right for those looking for the illusion of a little extra length!). Also available in two other colors.
To buy: $150; clarksusa.com.
Cole Haan Linnie Bootie
At $280, these ankle boots may seem a bit pricey, but the investment will pay off. The taupe suede is a classic color that works with everything, and they’re made with Cole Haan’s new Grand.OS technology, which blends flexibility, breathability, and cushioning for a three-and-a-half inch heel you can actually walk in. Available in two other colors.
To buy: $140; zappos.com.
Coldwater Creek Journey Suede Ankle Boots
This laid-back style—complete with cushioned footbeds and a non-slip rubber sole—is poised to become your go-to weekend shoe. Sleek black gives the traditional desert boot silhouette a modern spin. Also available in brown.
To buy: $80; coldwatercreek.com.
ECCO Shape 75 Leather Wraparound Ankle Boots
Add instant polish to skinny jeans and a sweater. Don’t let the 3-inch heel put you off—with a molded, anatomical footbed, leather sock lining, and injected PU-sole, they’re just as comfortable as your favorite flats.
To buy: $190; dillards.com.
SO Video Moto Boots
Take moto boots up a sartorial notch or two—this pair features a layered appeal thanks to the knit insert that’s just as warm and cozy as it looks. Also available in two other colors.
To buy: $70; kohls.com.