Men's Chukka Boots & Chelsea Boots

116 Total Items

116 Total Items

Men's HEYDUDE Tahoe Chelsea Classic Chelsea Boots in Brown/Wood/Ash color
HEYDUDE
$94.99

Men's HEYDUDE Tahoe Chelsea Classic Chelsea Boots

$94.99

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Men's Caterpillar Striver Chelsea Work Boots in Brown color
Caterpillar
$114.99

Men's Caterpillar Striver Chelsea Work Boots

$114.99
Men's Dockers Camden Dress Shoes in Black color
Dockers
$84.99
$49.98

Men's Dockers Camden Dress Shoes

$84.99
$49.98
Men's Freeman Brent Chukka Boots in Tan color
Freeman
$79.99
$69.98

Men's Freeman Brent Chukka Boots

$79.99
$69.98
Men's HEYDUDE Bradley Chukka Classic Boots in Brown/Black color
HEYDUDE
$84.99

Men's HEYDUDE Bradley Chukka Classic Boots

$84.99

See Price in Bag

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Men's HEYDUDE Bradley Chukka Classic Boots in Black/Grey color
HEYDUDE
$84.99

Men's HEYDUDE Bradley Chukka Classic Boots

$84.99

See Price in Bag

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Men's Tommy Hilfiger Harbin Chukka Boots in Cognac color
Tommy Hilfiger
$119.99
$59.98

Men's Tommy Hilfiger Harbin Chukka Boots

$119.99
$59.98
Men's Florsheim Forge Plain Toe Chukka Dress Boots in Black color
Florsheim
$129.99
$109.98

Men's Florsheim Forge Plain Toe Chukka Dress Boots

$129.99
$109.98
Men's Freeman Clay Dress Shoes in Black color
Freeman
$74.99
$54.98

Men's Freeman Clay Dress Shoes

$74.99
$54.98
Men's Georgia Boot Eagle One Waterproof Chelsea Work Boots in Brown color
Georgia Boot
$169.99

Men's Georgia Boot Eagle One Waterproof Chelsea Work Boots

$169.99
Men's Nunn Bush Circuit DC Plain Toe Chukka Boots in Brown Multi color
Nunn Bush
$89.99
$64.98

Men's Nunn Bush Circuit DC Plain Toe Chukka Boots

$89.99
$64.98
Men's Vance Co. Landon Chelsea Boots in Black color

+4 Colors

Vance Co.
$84.99
$49.98

Men's Vance Co. Landon Chelsea Boots

$84.99
$49.98
Men's Clarks Bushacre 2 Chukka Boots in Dark Brown color
Clarks
$99.99
$79.98

Men's Clarks Bushacre 2 Chukka Boots

$99.99
$79.98
Men's Florsheim Anthem Plain Toe Chukka Boot Chukka Boots in Saddle Tan color
Florsheim
$144.99

Men's Florsheim Anthem Plain Toe Chukka Boot Chukka Boots

$144.99
Men's Florsheim Anthem Plain Toe Chukka Boot Chukka Boots in Mocha color
Florsheim
$144.99

Men's Florsheim Anthem Plain Toe Chukka Boot Chukka Boots

$144.99
Men's Florsheim Anthem Plain Toe Chukka Boot Chukka Boots in Crazy Horse Br color
Florsheim
$144.99

Men's Florsheim Anthem Plain Toe Chukka Boot Chukka Boots

$144.99
Men's Florsheim Anthem Plain Toe Chukka Boot Chukka Boots in Black color
Florsheim
$144.99

Men's Florsheim Anthem Plain Toe Chukka Boot Chukka Boots

$144.99
Men's Dingo Boot Camino Chelsea Boots in Black color
Dingo Boot
$149.00

Men's Dingo Boot Camino Chelsea Boots

$149.00
Men's Florsheim Anthem Plain Toe Gore Boot Chelsea Boots in Saddle Tan color
Florsheim
$144.99

Men's Florsheim Anthem Plain Toe Gore Boot Chelsea Boots

$144.99
Men's Florsheim Anthem Plain Toe Gore Boot Chelsea Boots in Mocha color
Florsheim
$144.99

Men's Florsheim Anthem Plain Toe Gore Boot Chelsea Boots

$144.99
Men's Florsheim Anthem Plain Toe Gore Boot Chelsea Boots in Crazy Horse Br color
Florsheim
$144.99

Men's Florsheim Anthem Plain Toe Gore Boot Chelsea Boots

$144.99
Men's Florsheim Anthem Plain Toe Gore Boot Chelsea Boots in Black color
Florsheim
$144.99

Men's Florsheim Anthem Plain Toe Gore Boot Chelsea Boots

$144.99
Men's Born Harrison Chukka Shoe in Black color
Born
$144.99

Men's Born Harrison Chukka Shoe

$144.99
Men's Carhartt Detroit ESD Chukka Work Boots in Black/Gum color
Carhartt
$124.99

Men's Carhartt Detroit ESD Chukka Work Boots

$124.99

Shop Chukka Boots and Chelsea Boots for Men

Shop the latest trends in slip-on boots and dress boots for men! Men's Chelsea boots are the perfect fit when comfort, durability, and style are on the agenda. Or look dapper for work or play in a new pair of Chukka boots. You can find all your favorite men's boot brands at Shoe Carnival! Browse great deals on Stacy Adams, Clarks, Timberland, Vance Co., and so many more. Our selection of men's boots is unmatched so unbox your new pair today. Looking for sales on shoes? Shoe Carnival has you covered!

Are Chelsea Boots and Chukka Boots Still in Style?

YES! Chelsea boots inherited their name from their popularity in the trendy area of Chelsea, London during the mid 20th century, particularly on the mod scene. This trend certainly hasn't gone out of style and there's nothing like being able to slip into a pair of fashionable footwear when you're on the go. The style and versatility of Chukka boots will never get old. Find all the styles you need and love, at the best online shoe store! From black Chelsea boots for a night out, to fashionable brown Chukka dress boots for the office. Unbox them all at Shoe Carnival! We offer the widest selection of boots for men from the most trusted footwear brands.

Want your footwear faster? Buy online and pickup in-store at a Shoe Carnival store near you. Or have them delivered straight to your door. Shoe Perks members get free shipping on all orders from our online shoe store!