Highsnobiety / Asia Typek

You can smarten up your sneaker rotation as much as you like, but some occasions are simply no kicks zones. Fortunately, not only are ankle-high boots much more weather-appropriate through the fall/winter season, 2018’s luxury offering abounds with both smart leather options and high fashion takes on hiking-primed footwear.

Leading the way on the luxury front, Chelsea boots were popularized in the ’60s as the de facto footwear for London’s affluent King’s Road dwellers as well as the mod subculture taking over London elsewhere. Now, the style has been adopted by fashion houses all over in both slick and chunky silhouettes, boasting a versatility that can sharpen up any ’fit or give it a less polished edge.

On the other end of the spectrum, hiking boots have emerged as a footwear style no longer reserved for naturists. Once considered a niche purchase, the likes of ROA and Camper Lab have taken the shoe into more fashion-forward realms. Now, even the likes of Gucci are coming forward with hiking boots designed to face the elements and provide an elevated alternative to durable standard-issue sneakers.

Below, we’ve rounded up our very favorite luxury leather boots and high fashion hiking offerings to invest in for the season ahead. Scroll on for some ankle-high inspiration.

Luxury Leather Boots

Highlights of FW18’s luxury leather styles come from Prada‘s crackle effect Chelsea boots, which really make a statement in their white colorway. We’re also digging a chunky iteration from TAKAHIROMIYASHITA TheSoloist and lower-key offerings from Common Projects, R.M. Williams, and Marsèll.

Chelsea boots

Common Projects


Western Ankle Boots

Calvin Klein 205W39NYC


Crackle Effect



Crackle Ankle Boots



Chelsea Boots



Chelsea Boots

R.M. Williams


Chelsea Boots



Leather Boot



Luxury Outdoor Boots

1017 ALYX 9SM can do no wrong in 2018, and its hiking boot — boasting technical fabric and knit uppers on Vibram sole units — are no exception. Meanwhile, more highlights come from the bulkier silhouette Gucci Flashtrek and Camper Lab x Kiko Kostadinov high-top leather number.

Hiking Boot Trainers

1017 ALYX 9SM


Knit Hiking Boots

1017 ALYX 9SM


Flashtrek High



Ankle Boots



Leather Boots

Camper Lab x Kiko Kostadinov


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