When you buy through our links, we may earn a commission. Learn more ›
Wiki Shopping
Wiki Shopping
TipsLearnAbout
Wiki Shopping

Ankle and Chukka Boots

All shoes

7 ankle and chukka boots from Xtratuf, Cole Haan, Dream Pairs and more. Most cost $34 to $168, and half cost less than $68.

Top brands: Skechers (4)

All filtersFilters (2)×
Boot style: Ankle or chukka  ×Slip-on: Slip-on  ×Clear all
BrandSkechers4Bruno Marc1Dream Pairs1Jousen1
GenderWomen6Men1
TypeBoots7
Boot styleAnkle or chukka7
Slip-onSlip-on7
PriceUnder $502Under $753Under $1004Under $1502Under $2001Under $2501$50 & above3$100 & above1$150 & above1
Clear allShow 7 shoes
Boot style: Ankle or chukka  ×Slip-on: Slip-on  ×7 resultsSort byRecommendedSpec scorePrice: low to highPrice: high to low
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
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.
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
Jousen

Men, Boots, Ankle or chukka

+Slip-on design for quick on and off
+Ankle or chukka boot height
+Faux crocodile textured leather upper
−Faux leather upper rather than genuine leather
No price recorded yet.
Skechers

Women, Boots, Ankle or chukka

+Hands-free slip-in design for easy entry
+Chukka boot height for everyday wear
+Women's boot in size 8.5 medium
$82.03-14%List: $95.00
as of 11/04/2026 03:38 PST - Details
Bruno Marc

Women, Boots, Ankle or chukka

+Slip-on design with no laces to tie
+Ankle boot height for everyday wear
+Faux fur lining for warmth in cold weather
−Fur lining adds bulk in narrow footwear
$36.99
as of 11/04/2026 14:37 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

Compare specs

pair of shoesGenderTypeBoot styleSpec scorePrice
WomenBootsAnkle or chukkan/a$68.00
as of 11/04/2026 03:38 PST - Details
WomenBootsAnkle or chukkan/aNo current price
WomenBootsAnkle or chukkan/a$34.19
as of 11/03/2026 22:43 PST - Details
MenBootsAnkle or chukkan/aNo current price
WomenBootsAnkle or chukkan/a$82.03
as of 11/04/2026 03:38 PST - Details
WomenBootsAnkle or chukkan/a$36.99
as of 11/04/2026 14:37 PST - Details
WomenBootsAnkle or chukkan/a$168.67
as of 11/04/2026 03:38 PST - Details

Before you buy

Other Boot style options

Sneakers3,380Dresses2,052Jeans1,229Handbags & Shoulder Bags98Boys' Jewelry52Briefcases53Gym Bags63Laptop Bags75Suitcases64Messenger Bags59Travel Duffels52Travel Totes36

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.