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Ankle and Chukka Boots

All shoes

4 ankle and chukka boots from Xtratuf, Cole Haan, Dream Pairs and more. Prices run $27 to $119.

All filtersFilters (2)×
Gender: Unisex  ×Boot style: Ankle or chukka  ×Clear all
BrandDr. Martens2FlexStrap1Silvert's Adaptive Clothing & Footwear1
GenderMen76Women71Unisex4
TypeBoots4
Boot styleAnkle or chukka4
PriceUnder $502Under $752Under $1003Under $1502Under $2001$50 & above2$100 & above1
Clear allShow 4 shoes
Gender: Unisex  ×Boot style: Ankle or chukka  ×4 resultsSort byRecommendedSpec scorePrice: low to highPrice: high to low
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 11/03/2026 22:42 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
Silvert's Adaptive Clothing & Footwear

Unisex, Boots, Ankle or chukka

+Extra wide width for a roomy fit
+Soft fleece lining for warmth
+Unisex bootie style with ankle or chukka height
$26.98
as of 11/04/2026 03:35 PST - Details
Dr. Martens

Unisex, Boots, Ankle or chukka

+Ankle-height chukka boot style
+Nylon upper for a lighter-weight material than leather
+Unisex sizing covers both women and men
$119.99
as of 11/03/2026 22:42 PST - Details

Compare specs

pair of shoesGenderTypeBoot styleSpec scorePrice
UnisexBootsAnkle or chukkan/a$91.48
as of 11/03/2026 22:42 PST - Details
UnisexBootsAnkle or chukkan/a$31.99
as of 11/04/2026 00:41 PST - Details
UnisexBootsAnkle or chukkan/a$26.98
as of 11/04/2026 03:35 PST - Details
UnisexBootsAnkle or chukkan/a$119.99
as of 11/03/2026 22:42 PST - Details

Before you buy

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Popular filters

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