Nunn Bush
Men, Boots, Ankle or chukka
+Wide fit available for a roomier dress boot
+Full leather upper for a refined look
+Wingtip detailing adds classic dress styling
−Leather upper needs more care than synthetic materials
$72.45-40%List: $120.00
as of 11/04/2026 00:29 PST - DetailsProduct details
Pros+Wide fit available for a roomier dress boot
+Full leather upper for a refined look
+Wingtip detailing adds classic dress styling
+Chukka ankle height suits dress and casual wear
Cons−Leather upper needs more care than synthetic materials
How pros and cons are picked (About: Disclaimer) About this product
Dockers
Men, Boots, Ankle or chukka
+Ankle-height chukka boot with a rugged look
+Boot style suits casual and workwear settings
+Men's size 9.5 M in dark brown
$56.53-40%List: $95.00
as of 11/03/2026 22:41 PST - DetailsProduct details
About this product
Dockers
Men, Boots, Ankle or chukka
+Ankle-height chukka boot with a rugged build
+Boot style suits casual and workwear settings
+Men's size 11 M in briar
$59.99-37%List: $95.00
as of 11/03/2026 22:41 PST - DetailsProduct details
About this product
Xtratuf
Women, Boots, Ankle or chukka
+100% waterproof rubber construction
+Ankle-height deck boot design
+Lightweight for a rubber boot
$99.95-23%Was: $130.00
as of 11/04/2026 08:39 PST - DetailsProduct details
About this product
Skechers
Women, Boots, Ankle or chukka
+Available in an ankle or chukka boot height
+Slip-on design with hands-free entry
+Perform Tex feature named for water-resistant wear
$68.00-20%List: $85.00
as of 11/04/2026 03:38 PST - DetailsProduct details
About this product
Clarks
Women, Boots, Ankle or chukka
+Ankle boot style with a leather upper
+Available in size 8.5 medium width
+Women's cut for a standard fit
$95.99-11%Was: $108.00
as of 11/04/2026 15:39 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
Clarks
Women, Boots, Ankle or chukka
+Leather upper for a durable, structured build
+Ankle boot style suits everyday wear
+Black leather pairs with most outfits
−Ankle height offers less shaft coverage than knee-high boots
$95.99
as of 11/04/2026 15:39 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 73 shoes on this page+Waterproof: only 71 of 909 here have one
How pros and cons are picked (About: Disclaimer) About this product
Skechers
Men, Boots, Ankle or chukka
+Relaxed fit cut for a roomier feel
+Chukka boot style covers the ankle
+Designed for men in US size 13
$69.99
as of 11/04/2026 03:37 PST - DetailsProduct details
About this product
Dr.Scholl's SHOES
Men, Boots, Ankle or chukka
+Ankle boot style with a slip-resistant design
+Full-grain leather upper in black
+Wide width available in size 10.5
$54.98
as of 11/03/2026 22:42 PST - DetailsProduct details
About this product
Dr. Martens
Unisex, Boots, Ankle or chukka
+Chukka ankle boot style with six eyelets
+Lace-up closure for an adjustable fit
+Unisex sizing listed for men and women
$91.48
as of 11/03/2026 22:42 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 71 of 909 here have one
$140.00
as of 11/04/2026 08:39 PST - DetailsProduct details
About this product
Sperry
Men, Boots, Ankle or chukka
+Double sole construction adds sole thickness
+Chukka ankle height for added support
+Designed for men
$65.00-50%List: $130.00
as of 11/04/2026 04:38 PST - DetailsProduct details
About this product
Xtratuf
Women, Boots, Ankle or chukka
+6 inch ankle boot height for easy on and off
+Women's deck boot in size 10 for a snug fit
$69.00-45%List: $125.00
as of 11/04/2026 08:39 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
ARA
Boots, Ankle or chukka
+Ankle boot style for everyday wear
+Douglas model name offers a defined style
+Available in size 11
$144.32
as of 11/04/2026 11:42 PST - DetailsProduct details
About this product
Nine West
Women, Boots, Ankle or chukka
+Ankle bootie style with a suede leather upper
+Dark brown suede upper pairs with fall and winter outfits
+Women's ankle bootie in size 6.5
−Suede upper can show water marks in wet weather
$95.40-40%List: $159.00
as of 11/04/2026 00:26 PST - DetailsProduct details
Pros+Ankle bootie style with a suede leather upper
+Dark brown suede upper pairs with fall and winter outfits
+Women's ankle bootie in size 6.5
Cons−Suede upper can show water marks in wet weather
How pros and cons are picked (About: Disclaimer) About this product
Clarks
Men, Boots, Ankle or chukka
+Ankle-height boot cut for a streamlined profile
+Beeswax leather upper for a durable build
+Men's boot in size 9 width
$77.42-35%List: $120.00
as of 11/04/2026 15:39 PST - DetailsProduct details
About this product
Nine West
Women, Boots, Ankle or chukka
+Ankle bootie style with a suede leather upper
+Dark brown suede upper pairs with fall and winter outfits
+Women's ankle bootie in size 7
−Suede upper can show water marks in wet weather
$99.99-33%List: $149.00
as of 11/04/2026 00:26 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
