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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 $5029Under $7550Under $10069Under $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
Sioux

Men, Boots, Ankle or chukka

+Ankle or chukka boot style for everyday wear
+Men's boot cut with a classic boot silhouette
+Available in a 9 men's size
$192.36
as of 11/04/2026 03:36 PST - Details
Skechers

Women, Boots, Ankle or chukka

+Waterproof construction for wet conditions
+Ankle boot style for added coverage
+Slip-in design for quick on and off
$168.67
as of 11/04/2026 03:38 PST - Details
Stuart Weitzman

Women, Boots, Ankle or chukka

+Shearling lining adds warmth for cold weather
+Ankle bootie style offers coverage without a tall shaft
+Medium width listed for a standard fit
$750.00
as of 11/04/2026 04:41 PST - Details
TOMS

Women, Boots, Ankle or chukka

+Ankle or chukka boot height
+Wedge heel for added height
+Vintage check pattern in burgundy
$90.95
as of 11/04/2026 05:41 PST - Details
TOMS

Women, Boots, Ankle or chukka

+Genuine leather upper and lining
+Ankle-height bootie style
+Size 12 B(M) US available in tan mini cheetah suede
$90.95
as of 11/04/2026 05:41 PST - Details
Twisted X

Men, Boots, Ankle or chukka

+Chukka ankle boot style with a driving moc construction
+Available in medium width in size 7 for men
$139.95
as of 11/04/2026 06:38 PST - Details
Dream Pairs

Women, Boots, Ankle or chukka

+Platform wedge heel adds height and a stable base
+Ankle bootie height for everyday wear
$26.99
as of 11/03/2026 22:44 PST - Details
Stuart Weitzman

Women, Boots, Ankle or chukka

+Ankle or chukka bootie with a 50 heel height
+Medium width fit for standard feet
$650.00
as of 11/04/2026 04:41 PST - Details
Allen Edmonds

Men, Boots, Ankle or chukka

+Chukka ankle boot style for everyday wear
+Men's sizing in size 7.5 Medium
$525.00
as of 11/04/2026 11:36 PST - Details
Finn Comfort

Women, Boots, Ankle or chukka

+Ankle boot style with a women's fit
+Boot type suits cooler weather and extra ankle coverage
−Ankle height limits coverage compared with taller boots
$454.90
as of 11/03/2026 22:57 PST - Details

Compare specs

pair of shoesGenderTypeBoot styleSpec scorePrice
MenBootsAnkle or chukkan/a$192.36
as of 11/04/2026 03:36 PST - Details
WomenBootsAnkle or chukkan/a$168.67
as of 11/04/2026 03:38 PST - Details
WomenBootsAnkle or chukkan/a$750.00
as of 11/04/2026 04:41 PST - Details
WomenBootsAnkle or chukkan/a$90.95
as of 11/04/2026 05:41 PST - Details
WomenBootsAnkle or chukkan/a$90.95
as of 11/04/2026 05:41 PST - Details
MenBootsAnkle or chukkan/a$139.95
as of 11/04/2026 06:38 PST - Details
MenBootsAnkle or chukkan/a$119.90
as of 11/04/2026 15:41 PST - Details
WomenBootsAnkle or chukkan/a$26.99
as of 11/03/2026 22:44 PST - Details
WomenBootsAnkle or chukkan/a$650.00
as of 11/04/2026 04:41 PST - Details
MenBootsAnkle or chukkan/a$525.00
as of 11/04/2026 11:36 PST - Details

Before you buy

Other Boot style options

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Popular filters

Women's Shoes1,509Shoes under $1001,421Shoes under $751,223Men's Shoes927Shoes under $150912Boots876Shoes under $50848Leather and Suede Shoes646

Shoes by use

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

Related product types

Western Boots186Work Boots147Knee-High and Mid-Calf Boots77Rain and Snow Boots58

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