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 11/03/2026 22:33 PST - DetailsProduct details
About this product
Twisted X
Men, Boots, Ankle or chukka
+Chukka ankle boot style with a driving moc construction
+Available in medium width in size 11 for men
$139.99-7%List: $149.95
as of 11/04/2026 06:38 PST - DetailsProduct details
About this product
Xtratuf
Men, Boots, Ankle or chukka
+Ankle deck boot for work on wet decks
+Ankle-height shaft for easy on and off
+Chukka style with a classic boot profile
$115.00
as of 11/04/2026 08:39 PST - DetailsProduct details
About this product
Xtratuf
Women, Boots, Ankle or chukka
+Waterproof construction keeps feet dry in wet conditions
+Slip-resistant outsole adds traction on wet surfaces
+6 inch ankle height provides ankle coverage
$115.00
as of 11/04/2026 08:39 PST - DetailsProduct details
Pros+Waterproof construction keeps feet dry in wet conditions
+Slip-resistant outsole adds traction on wet surfaces
+6 inch ankle height provides ankle coverage
+Breathable design for more comfort than solid rubber boots
+Available in size 9 for women
Compared with the 49 shoes on this page+Waterproof: only 63 of 595 here have one
How pros and cons are picked (About: Disclaimer) 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
Xtratuf
Men, Boots, Ankle or chukka
+Ankle deck boot built for wet work surfaces
+Ankle-height shaft for easy on and off
+Chukka style with a classic boot profile
$115.00
as of 11/04/2026 08:39 PST - DetailsProduct details
About this product
Xtratuf
Men, Boots, Ankle or chukka
+Ankle deck boot built for wet work surfaces
+Sport style with an ankle-height shaft
+Chukka style with a low-profile fit
$140.00
as of 11/04/2026 08:39 PST - DetailsProduct details
About this product
Xtratuf
Men, Boots, Ankle or chukka
+100% waterproof rubber construction
+Ankle-height deck boot design
+Lightweight for a rubber boot
$140.00
as of 11/04/2026 08:39 PST - DetailsProduct details
About this product
Kickers
Men, Boots, Ankle or chukka
+High ankle boot height for added coverage
+Designed for men's sizing in size 10
+Classic boot style for everyday casual wear
$119.99
as of 11/03/2026 23:45 PST - DetailsProduct details
About this product
Twisted X
Women, Boots, Ankle or chukka
+Chukka boot cut sits at the ankle
+Driving moc construction for a slip-on fit
+Available in women's size 7 M
$131.13
as of 11/04/2026 06:38 PST - DetailsProduct details
About this product
Twisted X
Women, Boots, Ankle or chukka
+Chukka boot cut sits at the ankle
+Driving moc construction with a moc toe
+Available in women's size 7 M
$134.95
as of 11/04/2026 06:38 PST - DetailsProduct details
About this product
Xtratuf
Men, Boots, Ankle or chukka
+Waterproof: only 63 of 595 here have one
$140.00
as of 11/04/2026 08:39 PST - DetailsProduct details
About this product
Frye And CO.
Men, Boots, Ankle or chukka
+Ankle-height chukka boot style
+Men's boot in size 12 medium width
$129.99-32%List: $189.99
as of 11/03/2026 23:02 PST - DetailsProduct details
About this product
Steve Madden
Women, Boots, Ankle or chukka
+Ankle boot style for everyday wear
$101.37-8%List: $109.95
as of 11/04/2026 04:40 PST - DetailsProduct details
About this product
Dr. Martens
Unisex, Boots, Ankle or chukka
+Ankle-height chukka boot style
+Nylon upper for a lighter-weight material than leather
+Unisex sizing covers both women and men
$119.99
as of 11/03/2026 22:42 PST - DetailsProduct details
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 49 shoes on this page+Waterproof: only 63 of 595 here have one
How pros and cons are picked (About: Disclaimer) 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
Cole Haan
Men, Boots, Ankle or chukka
+Water resistant construction for wet conditions
+Leather upper for a durable build
+Chukka boot style suits casual outfits
$135.42-10%List: $150.00
as of 11/04/2026 15:41 PST - DetailsProduct details
Pros+Water resistant construction for wet conditions
+Leather upper for a durable build
+Chukka boot style suits casual outfits
Compared with the 49 shoes on this page+Waterproof: only 63 of 595 here have one
How pros and cons are picked (About: Disclaimer) About this product
Cole Haan
Men, Boots, Ankle or chukka
+Chukka boot style with an ankle-height cut
+Made with leather upper material
+Men's cut in medium width, size 8.5
$135.00-10%List: $150.00
as of 11/04/2026 15:41 PST - DetailsProduct details
About this product
Cole Haan
Men, Boots, Ankle or chukka
+Chukka boot style with ankle-height coverage
+Men's boot in size 12 W US width
$102.00-6%Was: $108.00
as of 11/04/2026 15:41 PST - DetailsProduct details
About this product
Steve Madden
Men, Boots, Ankle or chukka
+Genuine leather upper for a durable build
+Chukka ankle boot style
+Men's size 11 in black leather
−Glossy finish shows scuffs more readily than matte leather
$149.99
as of 11/04/2026 04:40 PST - DetailsProduct details
About this product
Xtratuf
Women, Boots, Ankle or chukka
+100% waterproof rubber construction keeps feet dry in wet conditions
+Lightweight build for comfortable all-day wear
+Ankle-height 6 inch boot for ankle coverage
−Rubber construction offers less ventilation than fabric footwear
$115.00
as of 11/04/2026 08:39 PST - DetailsProduct details
Pros+100% waterproof rubber construction keeps feet dry in wet conditions
+Lightweight build for comfortable all-day wear
+Ankle-height 6 inch boot for ankle coverage
+Non-marking sole suits indoor and deck use
+Available in size 7 for women
Cons−Rubber construction offers less ventilation than fabric footwear
Compared with the 49 shoes on this page+Waterproof: only 63 of 595 here have one
How pros and cons are picked (About: Disclaimer) About this product
Justin Reece England
Men, Boots, Ankle or chukka
+Ankle or chukka boot height for everyday wear
+Brogue pattern detailing adds classic styling
+Tweed checkered fabric upper for a textured look
−Tweed fabric is less suited to wet weather than leather
$134.96
as of 11/03/2026 23:42 PST - DetailsProduct details
Pros+Ankle or chukka boot height for everyday wear
+Brogue pattern detailing adds classic styling
+Tweed checkered fabric upper for a textured look
+Designed for men's sizing
Cons−Tweed fabric is less suited to wet weather than leather
How pros and cons are picked (About: Disclaimer) Cole Haan
Women, Boots, Ankle or chukka
+Waterproof leather boot for wet weather
+Full leather upper
+Chelsea style ankle boot is easy to pull on
$112.43
as of 11/04/2026 15:41 PST - DetailsProduct details
About this product
Rockport
Men, Boots, Ankle or chukka
+Waterproof construction for wet conditions
+Chukka boot style with ankle coverage
+Plain toe chocolate design in 8.5 US size
$119.95
as of 11/04/2026 01:36 PST - DetailsProduct details
Pros+Waterproof construction for wet conditions
+Chukka boot style with ankle coverage
+Plain toe chocolate design in 8.5 US size
Compared with the 49 shoes on this page+Waterproof: only 63 of 595 here have one
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
