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
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
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
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
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 11/03/2026 22:23 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
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
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
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 97 of 1223 here have one
$59.99-25%List: $79.99
as of 11/04/2026 00:03 PST - DetailsProduct details
About this product
Dream Pairs
Women, Boots, Ankle or chukka
+Slip-on design for quick wear
+High chunky block heel for added height
+Chelsea-style ankle boot silhouette
−Block heel adds height that may tire some wearers
$34.19-20%List: $42.99
as of 11/03/2026 22:43 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
Scurtain
Women, Boots, Ankle or chukka
+Available in wide or extra wide width
+Ankle-height boot style
+Furry lining for warmth
$29.99-19%List: $36.99
as of 11/04/2026 08:36 PST - DetailsProduct details
About this product
HEYDUDE
Women, Boots, Ankle or chukka
+Faux shearling lining adds warmth
+Elastic lace bootie style for easy on and off
+Textile upper for a lightweight feel
$63.31-16%List: $74.99
as of 11/03/2026 23:23 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
Dream Pairs
Women, Boots, Ankle or chukka
+Chunky block heel for stable everyday walking
+Platform sole adds height and grip
+Zipper closure for easy on and off
−Platform adds weight compared with flat boots
$42.99-14%List: $49.99
as of 11/03/2026 22:44 PST - DetailsProduct details
Pros+Chunky block heel for stable everyday walking
+Platform sole adds height and grip
+Zipper closure for easy on and off
+Ankle or chukka boot height
Cons−Platform adds weight compared with flat boots
How pros and cons are picked (About: Disclaimer) About this product
Skechers
Women, Boots, Ankle or chukka
+Ankle or chukka boot height for everyday wear
+Side zip closure for easy on and off
+Women's boot in size 9 medium
$65.24-13%List: $75.00
as of 11/04/2026 03:38 PST - DetailsProduct details
About this product
Dream Pairs
Women, Boots, Ankle or chukka
+Lug sole for added traction
+Side zipper for easy on and off
+Low chunky heel for stable walking
−Lug sole adds weight to the boot
$36.99-12%List: $41.99
as of 11/03/2026 22:43 PST - DetailsProduct details
About this product
Lugz
Men, Boots, Ankle or chukka
+Chukka ankle height for a classic casual style
+Designed for men as a fashion boot for everyday wear
$39.99-11%List: $44.99
as of 11/04/2026 00:03 PST - DetailsProduct details
About this product
Soda
Boots, Ankle or chukka
+Ankle boot height for everyday wear
+Lug sole for added traction
+Chunky heel for a sturdier stance
$44.98-10%List: $49.99
as of 11/04/2026 03:42 PST - DetailsProduct details
About this product
