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Ankle and Chukka Boots

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170 ankle and chukka boots from Xtratuf, Cole Haan, Dream Pairs and more. Most cost $39 to $650, and half cost less than $115.

Top brands: Skechers (11)Dream Pairs (11)Clarks (10)Stuart Weitzman (9)

All filtersFilters (1)×
Boot style: Ankle or chukka  ×Clear all
BrandCole Haan13Xtratuf13Dream Pairs11Skechers11Clarks10Giuseppe Zanotti10Stuart Weitzman9Steve Madden5
Show all 40Camper4Lugz4Timberland4TOMS4Twisted X4Allen Edmonds3Bruno Marc3Mephisto3Cushionaire2Dockers2Dr. Martens2Durango2Geox2HEYDUDE2Nine West2Nunn Bush2Salvatore Ferragamo2Soda2Sperry2Aerosoles1Amali1ARA1Ariat1Arkbird1Cestfini1Chooka1Dansko1Deer Stags1Dockers by Gerli1Dr.Scholl's SHOES1Easy Spirit1Finn Comfort1
GenderMen76Women71Unisex4
TypeBoots170
Boot styleAnkle or chukka170
Leather or suedeLeather or suede43
Slip-onSlip-on7
PriceUnder $253Under $5030Under $7550Under $10070Under $15075Under $20049Under $25019Under $3007
Show all 16Under $5003Under $6006Under $7008Under $8001$50 & above122$100 & above82$150 & above47$600 & above17
Clear allShow 170 shoes
Boot style: Ankle or chukka  ×170 resultsSort byRecommendedSpec scorePrice: low to highPrice: high to low
Skechers

Men, Boots, Ankle or chukka

+Ankle or chukka boot style for everyday wear
+Extra wide width in size 10 for broader feet
+Men's sizing in US size 10
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.
Allen Edmonds

Men, Boots, Ankle or chukka

+Chukka ankle boot style for everyday wear
+Men's sizing in size 14 D, including larger sizes
$525.00
as of 11/04/2026 11:36 PST - Details
Xtratuf

Men, Boots, Ankle or chukka

+Waterproof: only 23 of 170 here have one
$140.00
as of 11/04/2026 08:39 PST - Details
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 - Details
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 - Details
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 - 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
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 - Details
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 - 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
$69.99-30%List: $99.99
as of 11/04/2026 16:39 PST - Details
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 - Details
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 - 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

Compare specs

pair of shoesGenderTypeBoot styleSpec scorePrice
MenBootsAnkle or chukkan/aNo current price
WomenBootsAnkle or chukkan/a$694.20
as of 11/04/2026 04:41 PST - Details
WomenBootsAnkle or chukkan/a$131.13
as of 11/04/2026 06:38 PST - Details
WomenBootsAnkle or chukkan/a$134.95
as of 11/04/2026 06:38 PST - Details
WomenBootsAnkle or chukkan/a$650.00
as of 11/04/2026 04:41 PST - Details
WomenBootsAnkle or chukkan/a$650.00
as of 11/04/2026 04:41 PST - Details
WomenBootsAnkle or chukkan/aNo current price
MenBootsAnkle or chukkan/a$525.00
as of 11/04/2026 11:36 PST - Details
MenBootsAnkle or chukkan/a$140.00
as of 11/04/2026 08:39 PST - Details
WomenBootsAnkle or chukkan/a$36.00
as of 11/04/2026 15:39 PST - Details

Before you buy

Other Boot style options

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Popular filters

Women's Shoes1,510Shoes under $1001,420Shoes under $751,220Men's Shoes927Shoes under $150913Boots876Shoes under $50849Leather and Suede Shoes646

Shoes by use

Women's Boots284Men's Boots489Men's Dress Shoes99Women's Sandals347Waterproof Shoes204Wide Shoes186Steel Toe Shoes65

Related product types

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