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Ankle and Chukka Boots

All shoes

71 ankle and chukka boots from Xtratuf, Cole Haan, Dream Pairs and more. Most cost $34 to $650, and half cost less than $91.

Top brands: Dream Pairs (11)Skechers (9)Stuart Weitzman (9)Clarks (4)

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 - Details
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 - Details
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 - Details
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 - Details
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 - Details
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 - Details
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.
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 - Details
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 - Details
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 - Details
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.
Stuart Weitzman

Women, Boots, Ankle or chukka

+Stretch ankle bootie style with a chukka-style shaft
+Women's medium width in size 9
+Heel height of 85 for a taller stance
$694.20
as of 11/04/2026 04:41 PST - Details
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 - Details
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 - Details
Stuart Weitzman

Women, Boots, Ankle or chukka

+Zip booties with an ankle or chukka cut
+50 heel height for everyday wear
+Medium width fit for standard feet
$650.00
as of 11/04/2026 04:41 PST - Details
Stuart Weitzman

Women, Boots, Ankle or chukka

+Ankle bootie style with a chukka-style shaft
+Women's medium width fits a standard foot shape
+Available in size 8 medium
$650.00
as of 11/04/2026 04:41 PST - Details
Stuart Weitzman

Women, Boots, Ankle or chukka

+Ankle or chukka height offers versatile styling
+Stretch construction for a close fit
+Medium width fit in US size 8.5
No current price. Check it at the store.
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 - Details
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 - Details
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 - Details
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 - Details
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 - Details
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 - Details
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 - Details
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 - Details
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 - Details
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 - Details

Compare specs

pair of shoesGenderTypeBoot styleSpec scorePrice
WomenBootsAnkle or chukkan/a$33.99
as of 11/03/2026 22:43 PST - Details
WomenBootsAnkle or chukkan/a$99.95
as of 11/04/2026 08:39 PST - Details
WomenBootsAnkle or chukkan/a$68.00
as of 11/04/2026 03:38 PST - Details
WomenBootsAnkle or chukkan/a$83.34
as of 11/03/2026 22:23 PST - Details
WomenBootsAnkle or chukkan/a$95.99
as of 11/03/2026 22:23 PST - Details
WomenBootsAnkle or chukkan/a$42.99
as of 11/03/2026 22:43 PST - Details
WomenBootsAnkle or chukkan/aNo current price
WomenBootsAnkle or chukkan/a$115.00
as of 11/04/2026 08:39 PST - Details
WomenBootsAnkle or chukkan/a$180.00
as of 11/04/2026 07:38 PST - Details
WomenBootsAnkle or chukkan/a$159.95
as of 11/04/2026 04:40 PST - Details

Before you buy

Spec scores, pros and cons, and prices are explained in the How it works section of the About page.