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Ankle and Chukka Boots

All shoes

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)

LokoLucx

Men, Boots, Ankle or chukka

+Lace-up closure for a secure fit
+Ankle or chukka boot height
+Round toe suits everyday casual wear
$18.99
as of 11/04/2026 00:09 PST - Details
Cole Haan

Women, Boots, Ankle or chukka

+Chelsea boot with elastic side panels for easy pull-on wear
+Ankle or chukka height for everyday styling
+Leather suede upper for a soft texture
$165.00
as of 11/04/2026 15:41 PST - Details
Stuart Weitzman

Women, Boots, Ankle or chukka

+Ankle bootie style that covers the ankle
+Medium width fit available in size 11
+Chukka-style bootie for a low-profile ankle boot look
$650.00
as of 11/04/2026 04:41 PST - Details
Johnston & Murphy

Men, Boots, Ankle or chukka

+Chukka ankle boot style
+Full grain leather upper
+Available in men's size 10.5 medium width
$188.95
as of 11/03/2026 23:40 PST - Details
Florsheim

Men, Boots, Ankle or chukka

+Chukka ankle boot style for everyday wear
+Available in size 11 wide for a roomier fit
+Plain toe gives a clean, classic silhouette
$125.61
as of 11/03/2026 23:00 PST - Details
Timberland

Women, Boots, Ankle or chukka

+Full grain leather upper in an ankle-height Chelsea style
+Elastic side panels for easy on and off
+Medium width in size 8.5 US
$169.95
as of 11/04/2026 05:40 PST - Details
Timberland

Men, Boots, Ankle or chukka

+Waterproof construction for wet weather wear
+Chukka boot style with an ankle-height cut
+Men's sizing in size 11 medium
$122.52
as of 11/04/2026 05:40 PST - Details
Easy Spirit

Women, Boots, Ankle or chukka

+Ankle boot style with a low heel
+Available in women's size 8 wide width
+Ankle or chukka boot style for casual wear
No price recorded yet.
Stuart Weitzman

Women, Boots, Ankle or chukka

+Ankle bootie style with a zipper closure for easy on and off
+Medium width fit available in size 9
+Chukka-style bootie for a low-profile ankle boot look
$595.00
as of 11/04/2026 04:41 PST - Details
Stuart Weitzman

Women, Boots, Ankle or chukka

+Ankle or chukka boot style for everyday wear
+Women's boot in a size 8 medium width
+Zip closure for easy on and off
$695.00
as of 11/04/2026 04:41 PST - Details
Cole Haan

Men, Boots, Ankle or chukka

+Chukka boot style with an ankle-height cut
+Men's cut in wide width, size 13
+Boot style suits everyday casual wear
$132.65
as of 11/04/2026 15:41 PST - Details
Camper

Men, Boots, Ankle or chukka

+Ankle boot design covers the ankle for everyday wear
+Available in size 9 US for men
+Brutus+ model offers a sturdy boot style
$240.00
as of 11/04/2026 14:39 PST - Details
Cole Haan

Men, Boots, Ankle or chukka

+Chukka boot style with an ankle-height cut
+Men's cut in wide width, size 10.5
+Boot style suits everyday casual wear
$132.75
as of 11/04/2026 15:41 PST - Details
Durango

Boots, Ankle or chukka

+Ankle-height chukka boot for easy on and off
+Ultra-lite construction for lighter daily wear
+Size 8 wide width for a roomier fit
No price recorded yet.
Camper

Men, Boots, Ankle or chukka

+Ankle boot design covers the ankle for everyday wear
+Available in size 7 US for men
+Brutus+ model offers a sturdy boot style
$275.00
as of 11/04/2026 14:39 PST - Details
Durango

Boots, Ankle or chukka

+Ankle-height chukka boot for easy on and off
+Ultra-lite construction for lighter daily wear
+Size 11.5 wide width for a roomier fit
$170.00
as of 11/03/2026 22:45 PST - Details
UGG

Men, Boots, Ankle or chukka

+Waterproof construction for wet weather wear
+Chukka ankle-height boot style
+Available in a medium width size
$134.85
as of 11/04/2026 06:38 PST - Details
TOMS

Women, Boots, Ankle or chukka

+Leather upper for a durable, structured boot
+Ankle bootie style for everyday wear
+Designed for women's feet in an 8.5 medium fit
$90.95
as of 11/04/2026 05:41 PST - Details
Clarks

Men, Boots, Ankle or chukka

+Leather upper for a durable boot
+High chukka height for more ankle coverage
+Medium width in US size 8
$120.99
as of 11/04/2026 15:39 PST - Details
Camper

Men, Boots, Ankle or chukka

+Ankle boot design covers the ankle for everyday wear
+Available in size 8 US for men
+Brutus+ model offers a sturdy boot style
$235.00
as of 11/04/2026 14:39 PST - Details
TOMS

Women, Boots, Ankle or chukka

+Leather upper for a durable, structured boot
+Ankle bootie style for everyday wear
+Designed for women's feet in a size 5 fit
$90.95
as of 11/04/2026 05:41 PST - Details
Clarks

Men, Boots, Ankle or chukka

+Ankle-height chukka cut for a classic boot silhouette
+Full-grain beeswax leather upper for durability
+Men's boot in size 12 medium width
$99.00
as of 11/04/2026 15:39 PST - Details
Cole Haan

Men, Boots, Ankle or chukka

+Chukka boot style with an ankle-height cut
+Men's cut in wide width, size 11
+Boot style suits everyday casual wear
$133.57
as of 11/04/2026 15:41 PST - Details
Geox

Women, Boots, Ankle or chukka

+Ankle boot style with a versatile everyday silhouette
+Sized in US 4.5 for a smaller fit
+Designed for women
$133.01
as of 11/03/2026 23:11 PST - Details
Mephisto

Men, Boots, Ankle or chukka

+Water-resistant construction for wet conditions
+Ankle boot height suits both dress and casual wear
+Medium width offers a standard fit
$498.90
as of 11/04/2026 00:10 PST - Details

Compare specs

pair of shoesGenderTypeBoot styleSpec scorePrice
MenBootsAnkle or chukkan/a$18.99
as of 11/04/2026 00:09 PST - Details
WomenBootsAnkle or chukkan/a$165.00
as of 11/04/2026 15:41 PST - Details
WomenBootsAnkle or chukkan/a$650.00
as of 11/04/2026 04:41 PST - Details
MenBootsAnkle or chukkan/a$188.95
as of 11/03/2026 23:40 PST - Details
MenBootsAnkle or chukkan/a$125.61
as of 11/03/2026 23:00 PST - Details
WomenBootsAnkle or chukkan/a$169.95
as of 11/04/2026 05:40 PST - Details
MenBootsAnkle or chukkan/a$122.52
as of 11/04/2026 05:40 PST - Details
WomenBootsAnkle or chukkan/aNo current price
WomenBootsAnkle or chukkan/aNo current price
WomenBootsAnkle or chukkan/a$595.00
as of 11/04/2026 04:41 PST - Details

Before you buy

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