381 items, cheapest first

See all cheapest boots for men

• 

  Logan Round Toe Pull On Chelsea Boots

  Shoebacca

  $39.97 Not really a sale

  Quality: Good

  11.5checked 29h ago

• 

  Chelsea Boots for Men

  Old Navy · Cognac Brown

  $59.99

  Quality: Fair

  8 9 9.5 10 10.5 11 11.5 12 13checked 7h ago

• 

  Chelsea Boots for Men

  Old Navy · Black Jack

  $59.99

  Quality: Fair

  8 9 9.5 10 10.5 11 11.5 12 13checked 7h ago

• 

  Chelsea Rain Boot - Men's Black

  DSW

  $59.99

  Quality: Good

  checked 8h ago

• 

  Brady Plain Toe Chelsea Boots

  Zappos · Black

  $61.55 Not really a sale

  Quality: Good

  checked 13h ago

• 

  Vance Men's Co. Marshon Chelsea Boot

  American Eagle · Gray

  $64.99

  Quality: Fair

  checked 8h ago

• 

  Vance Men's Co. Marshon Chelsea Boot

  American Eagle · Tan

  $64.99

  Quality: Fair

  checked 8h ago

• 

  Men's Caterpillar, Striver Chelsea Waterproof Steel Toe Work Boot

  Peltz Shoes

  $65.97 Not really a sale

  Quality: Very good

  13checked 31h ago

• 

  Stonington Chelsea Boot Suede

  Zappos · Deepest Brown

  $69.50 Dropped

  Quality: Good

  checked 13h ago

• 

  FRANCO FORTINI MENS GLORY CHELSEA BOOT - BLACK

  Rack Room Shoes

  $69.99

  Quality: Good

  checked 7h ago

• 

  FRANCO FORTINI MENS RON CHELSEA BOOT - BROWN

  Rack Room Shoes

  $69.99

  Quality: Good

  checked 7h ago

• 

  RESTORATION MENS AUSTIN CHELSEA BOOT - BLACK

  Rack Room Shoes

  $69.99

  Quality: Good

  checked 8h ago

• 

  RESTORATION MENS AUSTIN CHELSEA BOOT - BROWN

  Rack Room Shoes

  $69.99

  Quality: Good

  checked 8h ago

• 

  Karnak Plain Toe Chelsea Boots Lightweight Comfortable Chukka

  Zappos · Black

  $72 Not really a sale

  Quality: Good

  checked 13h ago

• 

  Connor Chelsea

  Frye · Black

  $79.98 Not really a sale

  Quality: Very good

  8.5 9 9.5 10 10.5 12 13checked 30h ago

• 

  Connor Chelsea

  Frye · Dark Walnut

  $79.98 Not really a sale

  Quality: Very good

  8 8.5 9 9.5 10 10.5 12 13checked 30h ago

• 

  Connor Chelsea

  Frye · Mushroom

  $79.98 Not really a sale

  Quality: Very good

  8 8.5 9 9.5 10 10.5 11 11.5 12 13checked 30h ago

• 

  Cyrus Chelsea Boot - Men's Black

  DSW · 2 stores

  $84.99

  Quality: Good

  checked 25h ago

• 

  Chelsea Ankle Boots

  Shoebacca

  $84.99

  Quality: Good

  8 8.5 9 9.5 10 10.5 11 11.5 12 13checked 29h ago

• 

  Chelsea Ankle Boots

  Shoebacca

  $84.99

  Quality: Good

  8 8.5 9 9.5 10 10.5 11 11.5 12 13checked 29h ago

• 

  Briggs Plain Toe Chelsea Chukka Leather Boots

  Zappos · Black

  $89.95 Not really a sale

  Quality: Good

  checked 13h ago

• 

  Otis 2.0 Chelsea Fashion Leather Boots

  Zappos · Black

  $89.95 Not really a sale

  Quality: Good

  checked 13h ago

• 

  Redwood Edge Chelsea Boot - Men's Brown

  DSW · 4 stores

  $89.98

  Quality: Good

  checked 6h ago

• 

  VANCE CO MENS LANDON CHELSEA BOOT - WIDE - CHESTNUT

  Rack Room Shoes

  $89.99

  Quality: Good

  checked 5h ago

• 

  Eastland Men's Cyrus Chelsea Boot

  American Eagle · Black

  $90

  Quality: Fair

  checked 8h ago

• 

  Eastland Men's Cyrus Chelsea Boot

  American Eagle · Brown

  $90

  Quality: Fair

  checked 8h ago

• 

  NUNN BUSH MENS DELTON PLAIN TOE CHELSEA BOOT - BROWN

  Rack Room Shoes

  $94.99

  Quality: Good

  checked 10h ago

• 

  NUNN BUSH MENS DELTON PLAIN TOE CHELSEA BOOT - BLACK

  Rack Room Shoes

  $94.99

  Quality: Good

  checked 10h ago

• 

  NUNN BUSH MENS BRADY PLAIN TOE CHELSEA BOOT - BROWN

  Rack Room Shoes

  $94.99

  Quality: Good

  checked 7h ago

• 

  NUNN BUSH MENS BRADY PLAIN TOE CHELSEA BOOT - BLACK

  Rack Room Shoes

  $94.99

  Quality: Good

  checked 7h ago

• 

  DOCKERS MENS BLACKWELL BURNISHED CRAZYHORSE CHELSEA BOOT - DARK TAN

  Rack Room Shoes

  $94.99

  Quality: Good

  checked 7h ago

• 

  DOCKERS MENS BLACKWELL BURNISHED CRAZYHORSE CHELSEA BOOT - BLACK

  Rack Room Shoes

  $94.99

  Quality: Good

  checked 7h ago

• 

  Men's Chelsea Boot Tuff

  Lems Shoes · Ash (Final Sale)

  $97.50 Not really a sale

  Quality: Very good

  10 10.5 11 12 13checked 2d ago

• 

  Timberland Redwood Falls Chelsea

  Shoe Show

  $99.98

  Quality: Fair

  checked 8h ago

• 

  Sorel Ankeny II Chelsea Waterproof Winter Boot (Men's)

  Peter Glenn

  $99.99

  Quality: Good

  checked 9h ago

• 

  CATERPILLAR MENS THRESHOLD CHELSEA BOOT - GREY

  Rack Room Shoes

  $99.99

  Quality: Good

  checked 8h ago

• 

  Embury Chelsea Boot - Men's Gunmetal Grey

  DSW

  $104.98

  Quality: Good

  checked 5h ago

• 

  Men's Rainscape Chelsea Boot

  Murdoch's

  $104.99

  Quality: Good

  checked 9h ago

• 

  Caterpillar Striver Chelsea Steel-Toe

  Shoe Show

  $104.99 Dropped

  Quality: Good

  checked 9h ago

• 

  CATERPILLAR MENS STRIVER CHELSEA WP STEEL TOE WORK BOOT - BROWN

  Rack Room Shoes

  $104.99

  Quality: Very good

  checked 6h ago

• 

  Townsend Chelsea Boots

  Zappos · Black Tumble

  $105 Real deal

  Quality: Good

  checked 12h ago

• 

  Rancher Level Chelsea Slip-on Steel-toe Work Boot

  Zappos · Sudan Brown

  $109.95 Not really a sale

  Quality: Good

  checked 11h ago

• 

  Sauvie Chelsea II Boot - Men's Dark Brown

  DSW

  $109.99

  Quality: Good

  checked 5h ago

• 

  Striver Steel Toe Chelsea Work Boot - Men's Dark Brown

  DSW

  $109.99

  Quality: Very good

  checked 24h ago

• 

  Men's Marcello Waterproof Chelsea Boots

  Rockport · Medium Natural Suede

  $109.99 Real deal

  Quality: Good

  7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 13 14 15checked 7h ago

• 

  VANCE CO MENS SALTER CHELSEA BOOT - BLACK

  Rack Room Shoes

  $109.99

  Quality: Good

  checked 8h ago

• 

  VANCE CO MENS JOSIAH CHELSEA BOOT - DARK BROWN

  Rack Room Shoes

  $109.99

  Quality: Good

  checked 8h ago

• 

  VANCE CO MENS SALTER CHELSEA BOOT - BROWN

  Rack Room Shoes

  $109.99

  Quality: Good

  checked 8h ago