Crosby moc-toe chukka boot, $455 at Drake's

Brownflex Chukka Boot, $268 at Huckberry

Moc Toe Chukka Lug Sole Boot, $275 at Huckberry

Jibflex Lug Sole Chukka Boot, $298 at Huckberry

Original desert boot, $89.99 at Clarks

Clifford desert boot, $450 at Drake's

Weekender chukka, $269.99 at Red Wing

Polo Ralph Lauren Talan chukka, $298 at Ralph Lauren

Flint and Tinder x Rancourt & Co. Acadia Chukka Boot, $348/$244 at Huckberry

Jibflex Lug Sole Chukka Boot, $275/$192 at Huckberry

MacAlister chukka, $198 at J.Crew

Clarks Wallabee, $170/$102 at Todd Snyder

Astorflex Suede chukka, $250 at Huckberry

Astorflex Brownflex desert boot, $250 at Huckberry