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
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
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
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
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
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
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
Amali
Men, Boots, Ankle or chukka
+Suede upper with a crepe sole
+Ankle-height chukka boot with lace-up closure
+Made with leather for a natural material upper
$49.99-38%List: $79.99
as of 11/04/2026 11:37 PST - DetailsProduct details
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 11/03/2026 22:23 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
Cushionaire
Women, Boots, Ankle or chukka
+Water resistant suede upper
+Side gore panels for easy slip on
+Ankle boot style for everyday wear
$69.98-30%List: $99.99
as of 11/03/2026 22:32 PST - DetailsProduct details
About this product
Cushionaire
Women, Boots, Ankle or chukka
$59.99-25%List: $79.99
as of 11/03/2026 22:32 PST - DetailsProduct details
About this product
Lugz
Men, Boots, Ankle or chukka
+Waterproof: only 23 of 170 here have one
$59.99-25%List: $79.99
as of 11/04/2026 00:03 PST - DetailsProduct details
About this product
LongBay
Women, Boots, Ankle or chukka
+Memory foam insole for cushioned support
+Fluffy faux fur lining for warmth
+Ankle or chukka boot height for added coverage
$25.55-20%List: $31.95
as of 11/04/2026 00:02 PST - DetailsProduct details
About this product
Dream Pairs
Women, Boots, Ankle or chukka
+Lace-up ankle boot with leather upper
+Low-stacked heel for everyday wear
+Chic combat-style design with soft vegan materials
−Lace-up closure takes longer to put on than slip-ons
$38.99-15%List: $45.99
as of 11/03/2026 22:43 PST - DetailsProduct details
About this product
Jytdun
Men, Boots, Ankle or chukka
+Full leather upper
+Lace-up closure for a secure fit
+Dress style ankle boot
$59.50-15%List: $69.99
as of 11/03/2026 23:42 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
$135.63-10%List: $150.00
as of 11/03/2026 22:25 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 43 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
+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 11/03/2026 22:25 PST - DetailsProduct details
About this product
Lugz
Men, Boots, Ankle or chukka
$54.99-8%List: $60.00
as of 11/04/2026 00:03 PST - DetailsProduct details
About this product
Lee
Men, Boots, Ankle or chukka
+Ankle-height chukka boot style
+Leather-look upper with denim accents
+Men's boot in size 7 medium width
−Faux leather upper rather than full leather
$49.00
as of 11/03/2026 23:51 PST - DetailsProduct details
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
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
Salvatore Ferragamo
Men, Boots, Ankle or chukka
+Genuine leather upper for a refined dress look
+Ankle chukka cut suits business and smart casual wear
+Wide and extra wide width option for a range of foot shapes
−Leather upper needs regular care to stay in good condition
$585.00
as of 11/03/2026 22:57 PST - DetailsProduct details
Pros+Genuine leather upper for a refined dress look
+Ankle chukka cut suits business and smart casual wear
+Wide and extra wide width option for a range of foot shapes
Cons−Leather upper needs regular care to stay in good condition
How pros and cons are picked (About: Disclaimer) About this product
Salvatore Ferragamo
Men, Boots, Ankle or chukka
+Brown suede leather upper for a versatile look
+Ankle chukka cut for a clean, sleek profile
+EE width listed for a roomier fit
−Suede upper is more sensitive to moisture and stains than smooth leather
$625.00
as of 11/03/2026 22:57 PST - DetailsProduct details
Pros+Brown suede leather upper for a versatile look
+Ankle chukka cut for a clean, sleek profile
+EE width listed for a roomier fit
Cons−Suede upper is more sensitive to moisture and stains than smooth leather
How pros and cons are picked (About: Disclaimer) 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
Clarks
Men, Boots, Ankle or chukka
+Suede upper in sand for a classic chukka look
+Ankle-height chukka boot style
+Size 13 men's sizing for larger feet
−Suede needs care to resist water and stains
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