Dansko
Boots, Ankle or chukka
+Anti-fatigue rocker bottom promotes forward foot motion
+Made with leather upper for a durable construction
+Ankle boot style offers more coverage than a clog
$179.95
as of 11/04/2026 16:40 PST - DetailsProduct details
About this product
Cole Haan
Men, Boots, Ankle or chukka
+Waterproof construction for wet weather
+Chukka ankle boot style
+Men's boot in size 10 medium
$220.00
as of 11/04/2026 15:41 PST - DetailsProduct details
About this product
Vionic
Women, Boots, Ankle or chukka
+Ankle or chukka boot height
+Made with leather upper material
+Chelsea style with elastic side panels
$180.00
as of 11/04/2026 07:38 PST - DetailsProduct details
About this product
Steve Madden
Women, Boots, Ankle or chukka
+Ankle boot style for everyday wear with pants or dresses
+Made with leather upper for a classic boot look
+Available in size 7.5 for women
$159.95
as of 11/04/2026 04:40 PST - DetailsProduct details
About this product
Sorel
Men, Boots, Ankle or chukka
+Waterproof construction for wet conditions
+Ankle or chukka boot style
+Men's fit for everyday wear
$161.50-15%List: $190.00
as of 11/04/2026 04:38 PST - DetailsProduct details
About this product
Mephisto
Women, Boots, Ankle or chukka
+Full-grain leather upper for a durable build
+Ankle boot height suits everyday and dressy outfits
+Size 8 listed for a clear fit reference
−Leather upper needs regular conditioning to keep its finish
$225.00
as of 11/04/2026 00:39 PST - DetailsProduct details
Pros+Full-grain leather upper for a durable build
+Ankle boot height suits everyday and dressy outfits
+Size 8 listed for a clear fit reference
Cons−Leather upper needs regular conditioning to keep its finish
How pros and cons are picked (About: Disclaimer) About this product
Cole Haan
Men, Boots, Ankle or chukka
+Waterproof construction for wet weather
+Chukka ankle boot style
+Flexcraft design for added flexibility
$154.15-14%List: $180.00
as of 11/04/2026 15:41 PST - DetailsProduct details
Pros+Waterproof construction for wet weather
+Chukka ankle boot style
+Flexcraft design for added flexibility
+Men's boot in size 10.5 medium
Compared with the 19 shoes on this page+Waterproof: only 34 of 367 here have one
How pros and cons are picked (About: Disclaimer) About this product
Pikolinos
Men, Boots, Ankle or chukka
+Leather upper for a durable, classic boot
+Removable insole allows custom or replacement insoles
+Ankle or chukka boot style for everyday wear
−Leather upper needs regular conditioning to stay supported
$239.95
as of 11/04/2026 00:39 PST - DetailsProduct details
Pros+Leather upper for a durable, classic boot
+Removable insole allows custom or replacement insoles
+Ankle or chukka boot style for everyday wear
Cons−Leather upper needs regular conditioning to stay supported
How pros and cons are picked (About: Disclaimer) About this product
Ariat
Men, Boots, Ankle or chukka
+Ankle or chukka height for everyday wear
+Square toe with a Chelsea boot design
+Men's size 10.5 in medium width
$169.95
as of 11/04/2026 11:43 PST - DetailsProduct details
About this product
Hunter
Women, Boots, Ankle or chukka
+Ankle or chukka bootie style
+Medium width in size 11
+Designed for women
$185.00
as of 11/03/2026 23:32 PST - DetailsProduct details
About this product
Cole Haan
Women, Boots, Ankle or chukka
+Chelsea boot with elastic side panels for easy pull-on wear
+Ankle or chukka height for everyday styling
+Leather suede upper for a soft texture
$165.00
as of 11/04/2026 15:41 PST - DetailsProduct details
About this product
Johnston & Murphy
Men, Boots, Ankle or chukka
+Chukka ankle boot style
+Full grain leather upper
+Available in men's size 10.5 medium width
$188.95
as of 11/03/2026 23:40 PST - DetailsProduct details
About this product
Timberland
Women, Boots, Ankle or chukka
+Full grain leather upper in an ankle-height Chelsea style
+Elastic side panels for easy on and off
+Medium width in size 8.5 US
$169.95
as of 11/04/2026 05:40 PST - DetailsProduct details
About this product
Camper
Men, Boots, Ankle or chukka
+Ankle boot design covers the ankle for everyday wear
+Available in size 9 US for men
+Brutus+ model offers a sturdy boot style
$240.00
as of 11/04/2026 14:39 PST - DetailsProduct details
About this product
Durango
Boots, Ankle or chukka
+Ankle-height chukka boot for easy on and off
+Ultra-lite construction for lighter daily wear
+Size 11.5 wide width for a roomier fit
$170.00
as of 11/03/2026 22:45 PST - DetailsProduct details
About this product
Camper
Men, Boots, Ankle or chukka
+Ankle boot design covers the ankle for everyday wear
+Available in size 8 US for men
+Brutus+ model offers a sturdy boot style
$235.00
as of 11/04/2026 14:39 PST - DetailsProduct details
About this product
Sioux
Men, Boots, Ankle or chukka
+Ankle or chukka boot style for everyday wear
+Men's boot cut with a classic boot silhouette
+Available in a 9 men's size
$192.36
as of 11/04/2026 03:36 PST - DetailsProduct details
About this product
Skechers
Women, Boots, Ankle or chukka
+Waterproof construction for wet conditions
+Ankle boot style for added coverage
+Slip-in design for quick on and off
$168.67
as of 11/04/2026 03:38 PST - DetailsProduct details
Pros+Waterproof construction for wet conditions
+Ankle boot style for added coverage
+Slip-in design for quick on and off
+Air-cooled Goga Mat insole for ventilation
Compared with the 19 shoes on this page+Waterproof: only 34 of 367 here have one
How pros and cons are picked (About: Disclaimer) About this product
GANT
Men, Boots, Ankle or chukka
+Ankle or chukka boot style for everyday wear
+Designed for men in a size 10 fit
$171.28
as of 11/03/2026 23:07 PST - Details
