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clear allBoat Shoeclear filterChelseaclear filter
  • 115 Items
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Born Men's Hemlock Leather Chelsea BootsMen's Hemlock Leather Chelsea Boots

BornMen's Hemlock Leather Chelsea Boots

Extended Sizes
Rated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 stars(43)
Johnston & Murphy Men's XC+Durham Waterproof Leather Chelsea BootsMen's XC+Durham Waterproof Leather Chelsea Boots

Johnston & MurphyMen's XC+Durham Waterproof Leather Chelsea Boots

Extended Sizes
Rated 4.8571 out of 5 starsRated 4.8571 out of 5 starsRated 4.8571 out of 5 starsRated 4.8571 out of 5 starsRated 4.8571 out of 5 stars(7)
Sperry Men's Top-Sider Billfish 3-Eye Boat ShoesMen's Top-Sider Billfish 3-Eye Boat Shoes

SperryMen's Top-Sider Billfish 3-Eye Boat Shoes

Extended Sizes
Rated 4.6979 out of 5 starsRated 4.6979 out of 5 starsRated 4.6979 out of 5 starsRated 4.6979 out of 5 starsRated 4.6979 out of 5 stars(96)
Cole Haan Men's Pinch Leather Long-Weeknder Penny LoafersMen's Pinch Leather Long-Weeknder Penny Loafers

Cole HaanMen's Pinch Leather Long-Weeknder Penny Loafers

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(2)
Ariat Men's Booker Ultra Western Leather BootsMen's Booker Ultra Western Leather Boots

AriatMen's Booker Ultra Western Leather Boots

Extended Sizes
Rated 4.8057 out of 5 starsRated 4.8057 out of 5 starsRated 4.8057 out of 5 starsRated 4.8057 out of 5 starsRated 4.8057 out of 5 stars(978)
Johnston & Murphy Mens XC Flex Daylen Chelsea BootsMens XC Flex Daylen Chelsea Boots

Johnston & MurphyMens XC Flex Daylen Chelsea Boots

Internet Exclusive
Sperry Men's Top-Sider Gold Authentic Original 2-Eye Water Resistant Boat ShoesMen's Top-Sider Gold Authentic Original 2-Eye Water Resistant Boat Shoes

SperryMen's Top-Sider Gold Authentic Original 2-Eye Water Resistant Boat Shoes

Extended Sizes
Rated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 stars(21)
Cole Haan Men's Chamberlin Water Resistant Leather EVA Chelsea BootsMen's Chamberlin Water Resistant Leather EVA Chelsea Boots

Cole HaanMen's Chamberlin Water Resistant Leather EVA Chelsea Boots

Internet Exclusive
Men's Hemlock Leather Chelsea Boots

PLACEHOLDERMen's Hemlock Leather Chelsea Boots

Extended Sizes
Rated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 stars(43)

BlundstoneMen's Ant Brn 550 Water Resistant Antique Leather Chelsea Boots

Rated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 stars(14)

Johnston & MurphyMen's Calder Leather Chelsea Boots

Extended Sizes
Rated 3.68 out of 5 starsRated 3.68 out of 5 starsRated 3.68 out of 5 starsRated 3.68 out of 5 starsRated 3.68 out of 5 stars(25)

PLACEHOLDERMen's Hemlock Leather Chelsea Boots

Extended Sizes
Rated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 stars(43)

SperryMen's Top Sider Authentic Original 2 Eye Leather Boat Shoes

Extended Sizes
Rated 4.705 out of 5 starsRated 4.705 out of 5 starsRated 4.705 out of 5 starsRated 4.705 out of 5 starsRated 4.705 out of 5 stars(139)

Cole HaanMen's Windham Grand Chelsea Waterproof Boots

Internet Exclusive

PLACEHOLDERMen's Hemlock Leather Chelsea Boots

Extended Sizes
Rated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 stars(43)

Johnston & MurphyMen's XC Flex Daylen Chelsea Boots

BlundstoneMen's Ant Brn 550 Water Resistant Rustic Leather Chelsea Boots

Rated 4.913 out of 5 starsRated 4.913 out of 5 starsRated 4.913 out of 5 starsRated 4.913 out of 5 starsRated 4.913 out of 5 stars(23)

PLACEHOLDERMen's Hemlock Leather Chelsea Boots

Extended Sizes
Rated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 starsRated 4.6977 out of 5 stars(43)

AriatMen's Booker Ultra Western Boots

Extended Sizes
Rated 4.7998 out of 5 starsRated 4.7998 out of 5 starsRated 4.7998 out of 5 starsRated 4.7998 out of 5 starsRated 4.7998 out of 5 stars(859)

Johnston & MurphyMen's Reeve Leather Chelsea Zip Boots

Extended Sizes
Rated 4.3333 out of 5 starsRated 4.3333 out of 5 starsRated 4.3333 out of 5 starsRated 4.3333 out of 5 starsRated 4.3333 out of 5 stars(6)

Johnston & MurphyMen's XC+ Durham Cap Toe Waterproof Boots

SperryMen's Authentic Original 1-Eye Leather Boat Shoes

Johnston & MurphyMen's Conlin Leather Side Zip Boots

Internet Exclusive

FryeTyler Flex Leather Chelsea Boots

Internet Exclusive
Rated 3.2857 out of 5 starsRated 3.2857 out of 5 starsRated 3.2857 out of 5 starsRated 3.2857 out of 5 starsRated 3.2857 out of 5 stars(7)

ECCOMen's Milan Leather Chelsea Boots

Steve MaddenMen's Brompton Leather Chelsea Boots

SperryMen's Gold Water Resistant Leather Boat Shoes

Extended Sizes
Rated 4.5455 out of 5 starsRated 4.5455 out of 5 starsRated 4.5455 out of 5 starsRated 4.5455 out of 5 starsRated 4.5455 out of 5 stars(22)

Marc NolanMen's Dax Patent Leather Chelsea Boots

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(5)

Marc NolanMen's Dax Leather Western Chelsea Boots

Extended Sizes
Rated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 stars(3)

Polo Ralph LaurenMen's Bienne Leather Boat Shoes

Extended Sizes
Rated 4.8571 out of 5 starsRated 4.8571 out of 5 starsRated 4.8571 out of 5 starsRated 4.8571 out of 5 starsRated 4.8571 out of 5 stars(14)

Dr. MartensMen's 2976 Chelsea Boots

Extended Sizes
Rated 4.5208 out of 5 starsRated 4.5208 out of 5 starsRated 4.5208 out of 5 starsRated 4.5208 out of 5 starsRated 4.5208 out of 5 stars(48)

Cole HaanMen's Chamberlin Water Resistant Nubuck EVA Chelsea Boots

Johnston & MurphyMen's Ventura Leather 2-Eye Boat Shoes

Rated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 stars(9)

Section XMen's Steven Zip Oiled Leather Chelsea Boots

Dillard's Exclusive
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(3)

TimberlandMen's Portofino Pier Boat Shoes

Internet Exclusive
Extended Sizes
Rated 4.45 out of 5 starsRated 4.45 out of 5 starsRated 4.45 out of 5 starsRated 4.45 out of 5 starsRated 4.45 out of 5 stars(20)

SperryMen's Mako Nubuck 2-Eye Boat Shoes

Rated 4.9 out of 5 starsRated 4.9 out of 5 starsRated 4.9 out of 5 starsRated 4.9 out of 5 starsRated 4.9 out of 5 stars(20)

Steve MaddenMen's Highline Suede Chelsea Boots

Internet Exclusive
Extended Sizes
Rated 4.2 out of 5 starsRated 4.2 out of 5 starsRated 4.2 out of 5 starsRated 4.2 out of 5 starsRated 4.2 out of 5 stars(5)

AriatMen's Rambler Chelsea Boots

Rated 4.6186 out of 5 starsRated 4.6186 out of 5 starsRated 4.6186 out of 5 starsRated 4.6186 out of 5 starsRated 4.6186 out of 5 stars(312)

Section XMen's Steven Zip Nubuck Chelsea Boots

Dillard's Exclusive
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Steve MaddenMen's Brompton Suede Chelsea Boots

AriatMen's Cooper Water Resistant Leather Chelsea Boots

Rated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 stars(2)

TimberlandMen's 3-Eye Lug Handsewn Leather Boat Shoes

Extended Sizes
Rated 4.9268 out of 5 starsRated 4.9268 out of 5 starsRated 4.9268 out of 5 starsRated 4.9268 out of 5 starsRated 4.9268 out of 5 stars(41)

Section XMen's Steven Leather Zip Chelsea Boots

Dillard's Exclusive
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(3)

SperryMen's Helm 2-Eye Boat Sneakers

SperryMen's Billfish Slip On Boat Shoes

Rated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 stars(4)

TimberlandMen's Authentic 3-Eye Lug Handsewn Boat Shoes

Extended Sizes
Rated 4.5221 out of 5 starsRated 4.5221 out of 5 starsRated 4.5221 out of 5 starsRated 4.5221 out of 5 starsRated 4.5221 out of 5 stars(429)

SperryMen's Strake 2-Eye Boat Shoe Sneakers

UGGMen's Neumel Suede Chelsea Boots

Extended Sizes
Rated 4.8947 out of 5 starsRated 4.8947 out of 5 starsRated 4.8947 out of 5 starsRated 4.8947 out of 5 starsRated 4.8947 out of 5 stars(19)

AriatMen's Hilo Shore Distressed Leather Slip-Ons

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(4)

AriatMen's Rambler Recon Leather Square Toe Chelsea Boot

Rated 4.7692 out of 5 starsRated 4.7692 out of 5 starsRated 4.7692 out of 5 starsRated 4.7692 out of 5 starsRated 4.7692 out of 5 stars(13)

Marc NolanMen's Dax Croco Embossed Leather Chelsea Boots

Internet Exclusive
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(5)

BlundstoneMen's Water-Resistant Leather Chelsea Boots

BlundstoneMen's 550 Water Resistant Chelsea Boots

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

AriatMen's Hybrid Low Boy Boots

Rated 4.7156 out of 5 starsRated 4.7156 out of 5 starsRated 4.7156 out of 5 starsRated 4.7156 out of 5 starsRated 4.7156 out of 5 stars(225)

SperryMen's Authentic Original Boat Shoes

Extended Sizes

Marc NolanMen's Dante Leather Chelsea Boots

Extended Sizes

FryeMen's Paul Chukka Lite Boots

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

BlundstoneMen's Ant Brn 550 Water Resistant Leather Chelsea Boots

To Boot New YorkMen's Largo Chelsea Boots

Dune LondonMen's Matchin Leather Chelsea Boots

BirkenstockMen's Highwood Chelsea Boots

Internet Exclusive

Steve MaddenMen's Devera Leather Chelsea Boots

Internet Exclusive

Johnston & MurphyMen's Calder Suede Chelsea Boots

Extended Sizes
Rated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 stars(4)

Dr. MartensMen's 2976 Chelsea Boots

Internet Exclusive
Extended Sizes
Rated 4.6364 out of 5 starsRated 4.6364 out of 5 starsRated 4.6364 out of 5 starsRated 4.6364 out of 5 starsRated 4.6364 out of 5 stars(11)

Johnston & MurphyMen's Reeve Leather Chelsea Dress Boots

Extended Sizes

Johnston & MurphyCollection Men's Hartford Leather Chelsea Dress Boots

Internet Exclusive
Rated 3.6667 out of 5 starsRated 3.6667 out of 5 starsRated 3.6667 out of 5 starsRated 3.6667 out of 5 starsRated 3.6667 out of 5 stars(3)

Johnston & MurphyMen's Ripley Leather Zip Boots

Cole HaanMen's Chamberlin Water Resistant Nubuck Chelsea Boots

Internet Exclusive

Johnston & MurphyMen's Conlin Inside Zip Boots

Johnston & MurphyMens Barrett Suede Zip Boots

Internet Exclusive
Extended Sizes
Rated 1.5 out of 5 starsRated 1.5 out of 5 starsRated 1.5 out of 5 starsRated 1.5 out of 5 starsRated 1.5 out of 5 stars(2)

SperryMen's Authentic Original 1-Eye Suede Boat Shoes

Steve MaddenMen's Highline Leather Chelsea Boots

Internet Exclusive
Extended Sizes

SorelMen's Cyprus Waterproof Suede Chelsea Boots

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

FryeMen's Connor Leather Chelsea Boots

Rated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 stars(5)

Johnston & MurphyMen's Monaco Leather 2-Eye Boat Shoes

Internet Exclusive
Rated 4.8947 out of 5 starsRated 4.8947 out of 5 starsRated 4.8947 out of 5 starsRated 4.8947 out of 5 starsRated 4.8947 out of 5 stars(19)

AriatMen's Booker Leather Chelsea Boots

Internet Exclusive
Only size 9.5, 13 available
Rated 4.7991 out of 5 starsRated 4.7991 out of 5 starsRated 4.7991 out of 5 starsRated 4.7991 out of 5 starsRated 4.7991 out of 5 stars(856)

Bed StuMen's Michelangelo Rustic Leather Chelsea Boots

Internet Exclusive

L.L.BeanMen's Allagash Leather Handsewn 3-Eye Boat Shoes

Rated 3.8941 out of 5 starsRated 3.8941 out of 5 starsRated 3.8941 out of 5 starsRated 3.8941 out of 5 starsRated 3.8941 out of 5 stars(85)

ALIGNMen's Rangley Leather Chelsea Boots

Internet Exclusive

AriatMen's Wexford Waterproof Chelsea Boots

Rated 4.5424 out of 5 starsRated 4.5424 out of 5 starsRated 4.5424 out of 5 starsRated 4.5424 out of 5 starsRated 4.5424 out of 5 stars(295)

SperryMen's Authentic Original 2-Eye Boat Shoes

Extended Sizes

Johnston & MurphyMen's Clint Suede Slip On Chelsea Boot

Internet Exclusive

Steve MaddenMen's Avenue Suede Chelsea Boots

Internet Exclusive

Twisted XMen's Slip-On Chukka Leather Driving Moccasin Boots

Internet Exclusive
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(2)

Steve MaddenMen's Montreux Leather Chelsea Boots

Internet Exclusive
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Johnston & MurphyMen's Clint Leather Chelsea Boot

Internet Exclusive

Johnston & MurphyMen's XC+Durham Waterproof Suede Chelsea Boots

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(3)

UGGMen's Deckmel Boat Shoes

Internet Exclusive
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Johnston & MurphyCollection Men's Arrister Leather Chelsea Boots

Internet Exclusive

Steve MaddenMen's Hatton Suede Chelsea Boots

Internet Exclusive

Johnston & MurphyCollection Mens Hartford Chelsea Boots

Internet Exclusive

DannerMen's Bull Run Leather 6" Chelsea Boots

Extended Sizes

VionicMen's Uptown Boat Nubuck Suede Slip On Boat Shoes

Extended Sizes
Rated 4.5714 out of 5 starsRated 4.5714 out of 5 starsRated 4.5714 out of 5 starsRated 4.5714 out of 5 starsRated 4.5714 out of 5 stars(14)

FryeMen's Connor Suede Chelsea Boots

Internet Exclusive

Johnston & MurphyCollection Men's Hartford Pull Up Boots

Internet Exclusive

FryeMen's Mason Leather One Eye Tie Boat Shoes

Rated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 stars(2)

Johnston & MurphyCollection Men's Arrister Brush Finish Leather Chelsea Boots

Marc NolanMen's Capri Croco Embossed Leather Boat Shoes

Extended Sizes

Kurt Geiger LondonMen's Kurt's Cabana Multi Colored Deck Shoes

Extended Sizes
Frye Men's Connor Leather Boat ShoesMen's Connor Leather Boat Shoes

FryeMen's Connor Leather Boat Shoes

Internet Exclusive
Rated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 stars(4)
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