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 11/04/2026 17:37 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 11/04/2026 17:37 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
$37.99-25%List: $50.99
as of 11/04/2026 17:40 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
$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
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 11/04/2026 17:40 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
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 11/04/2026 17:39 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 11/04/2026 17:39 PST - DetailsProduct details
About this product
Clarks
Women, Boots, Ankle or chukka
+Ankle boot style for everyday wear
+Made of synthetic upper material in black
+Available in size 8.5 medium width
$36.00-58%List: $85.00
as of 11/04/2026 15:39 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
FlexStrap
Unisex, Boots, Ankle or chukka
+Plush lining keeps feet warm indoors
+Ankle bootie design covers more of the ankle
+Unisex sizing suits both women and men
−Plush booties are not built for outdoor wear
$31.99-9%List: $34.99
as of 11/04/2026 00:41 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
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 11/04/2026 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
Xtratuf
Men, Boots, Ankle or chukka
$78.82-31%List: $115.00
as of 11/04/2026 08:39 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
$69.99-30%List: $99.99
as of 11/04/2026 16:39 PST - DetailsProduct details
About this product
Timberland
Men, Boots, Ankle or chukka
+Chukka boot style with an ankle-height cut
+Men's sizing in 7 Medium width
$69.99-26%List: $95.00
as of 11/04/2026 05:40 PST - DetailsProduct details
About this product
Lugz
Men, Boots, Ankle or chukka
+Waterproof: only 108 of 1421 here have one
$59.99-25%List: $79.99
as of 11/04/2026 00:03 PST - DetailsProduct details
About this product
Clarks
Women, Boots, Ankle or chukka
$89.99-25%List: $120.00
as of 11/04/2026 15:40 PST - DetailsProduct details
About this product
Dream Pairs
Women, Boots, Ankle or chukka
+Platform sole adds height and stability
+Ankle-height boot for everyday wear
+Chunky heel for stable walking
−Platform sole adds bulk to the silhouette
$35.99-23%List: $46.99
as of 11/04/2026 17:40 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
