Nunn Bush
Boots, Ankle or chukka
+Plain toe chukka style suits business casual outfits
+Ankle height chukka cut for a versatile boot profile
+Classic boot design for everyday wear
$49.50-45%List: $90.00
as of 11/04/2026 00:29 PST - DetailsProduct details
About this product
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
Dream Pairs
Women, Boots, Ankle or chukka
+Platform sole adds height and stability
+Ankle height for everyday coverage
+Classic round toe design
$33.99-33%List: $50.99
as of 11/03/2026 22:43 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
+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
$83.34-13%Was: $95.99
as of 11/03/2026 22:23 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 11/03/2026 22:23 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
Dream Pairs
Women, Boots, Ankle or chukka
+Lace-up front with side zipper
+Chunky heel for stable walking
+Ankle-height boot for everyday wear
−Lace-up front takes longer to put on
$42.99
as of 11/03/2026 22:43 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
Skechers
Women, Boots, Ankle or chukka
+Hands-free slip-in design for quick wear
+Sweater knit upper adds a soft casual look
+Ankle or chukka height suits everyday outfits
No current price. Check it at the store.
Product 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 170 shoes on this page+Waterproof: only 23 of 170 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
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
Grundéns
Men, Boots, Ankle or chukka
+Waterproof construction keeps feet dry in wet conditions
+Insulated for warmth in cold environments
+Ankle boot style for solid foot coverage
No current price. Check it at the store.
Product details
Pros+Waterproof construction keeps feet dry in wet conditions
+Insulated for warmth in cold environments
+Ankle boot style for solid foot coverage
+Men's sizing for a men's fit
Compared with the 170 shoes on this page+Waterproof: only 23 of 170 here have one
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
+Men's boot in size 10 medium
$220.00
as of 11/03/2026 22:25 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
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
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
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
Women, Boots, Ankle or chukka
+100% waterproof rubber construction
+Ankle-height deck boot design
+Lightweight for a rubber boot
No current price. Check it at the store.
Product 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
Allen Edmonds
Men, Boots, Ankle or chukka
+Chukka boot style with an ankle-high cut
+Made of leather for a classic boot material
+Men's boot in size 14 D width
$525.00
as of 11/04/2026 11:36 PST - DetailsProduct details
About this product
