The Generic Man Handmade Caramel Leather Chukka Boots, Sz 44.5/US 11

Frye Carly Chukka Taupe Leather Suede Boots size 7

C$62

DIESEL Men’s Leather Chukka Ankle Boots Gray Green EU 43‎

C$68

Porsche Design Driving Shoes

C$198 C$500

Timberland Brown Leather Chukka Boots with Black Elastic Panels

C$185 C$280

New Anthony Veer Wright Moc Lace-Up Boots Men's Brown Suede size 12

C$175 C$300

Merrell Men's Charcoal Chukka Boots

C$47 C$80

Men's Black Leather Ankle Boots - Classic Zip Chelsea Style

C$250

Men's Suede Clarks Desert Boot - Taupe

C$65 C$190

Balmain x Maluma Bold Runner Sneakers Shoe Boot Rare

C$900 C$1,300

David’s made in Italy Men's Brown Lace-Up Leather Ankle Boots 11 D

C$195

Classic Men's Chelsea Boots in Dark Brown Suede

C$40

Blundstone Men's chisel toe like new

C$190 C$260

Clarks Brown Suede Chukka Boots

C$35 C$100

John Varvatos Men's Navy Corduroy Chukka Boots

C$145

Tod's - black calfskin Chukka Boots - Classic Lace-Up, rubber soles like new

C$165 C$995

Timberland Men Black Leather & Canvas Chukka Shoes, Size 7

C$25

UGG Men's Freamon HyperWeave Knit Chukka Sneaker Boots Navy Size 12

C$69

Josef Seibel Men’s Brown Leather Lace Up Ankle Boots 11 EU 44 Rustic

C$68 C$210

Men’s brown leather chukka boot

C$45

Vans Mid-Slip MTE Shoes Black Suede Men’s Size 13 VN000DANBLK 2025 NEW CHUKKA

C$105 C$999

Vans Mid-Slip MTE Shoes Black Suede Men’s Size 11 VN000DANBLK 2025 NEW CHUKKA

C$105 C$999

Vans Mid-Slip MTE Shoes Black Suede Men’s Size 12 VN000DANBLK 2025 NEW CHUKKA

C$105 C$999

Vans Mid-Slip MTE Shoes Black Suede Men’s Size 10 VN000DANBLK 2025 NEW CHUKKA

C$105 C$999

Vans Mid-Slip MTE Shoes Black Suede Men’s Size 9.5 VN000DANBLK 2025 NEW CHUKKA

C$105 C$999

NWT Zara × Clarks Leather Ankle Brown Boots EUR 38 Or US 5.5

C$180 C$250

Red Wing 8715 Men’s Brown Leather Chukka Boots Size 11

C$40 C$220

Men's Casual Tan Lace-Up Shoes

C$14

Sorel Madson II Waterproof Chukka Boot Brown Pebbled Leather Mens Size 9.5 /42.5

C$70

Adventure Moccasins great shape

C$60

Timberland Men's Blue Suade Chukka Shoes

C$35

Hush Puppie Boots

C$50

Clarks Extreme Comfort Moccasins

C$75

BRUNO MARC Men’s Black Chukka Chelsea Boot

C$90

Men’s Brown Cowboy Chukka Boots - Pull-On Ankle Boots

C$150

Men's Brown Cowboy Chukka Chelsea Boot - Slip-On Casual Chukka

C$150

Men's Wine Suede Chelsea Boots - Stylish Slip-On Ankle Boots

C$25

Rockport Modern Break Chukka Black Leather Boots US 12 in box.

C$65 C$140