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Size 8.5 Ankle Chelsea Boots

Name: Wexford Waterproof
Brand: Ariat
Price: $199.95 USD

74 items found

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Ariat - Wexford Waterproof. Color Dark Brown. $199.95. 4.7 out of 5 stars

Brand Name: Ariat
Product Name: Wexford Waterproof
Gender: Men's
Color: Dark Brown
Price: $199.95
Rating: 5Rated 5 stars out of 5(183)

Wolverine - Floorhand Waterproof Romeo. Color Dark Brown. Low Stock. On sale for $99.95. MSRP $110.00.. 3.5 out of 5 stars

6 left in stock

Brown Wolverine Floorhand Waterproof Romeo

Brand Name: Wolverine
Product Name: Floorhand Waterproof Romeo
Gender: Men's
Color: Dark Brown
Price: $99.95MSRP: $110.00
Rating: 4Rated 4 stars out of 5(4)

. Merrell - Moab Adventure 3 Chelsea Wp. Color Black. On sale for $150.00. MSRP $160.00..

Black Merrell Moab Adventure 3 Chelsea Wp

Brand Name: Merrell
Product Name: Moab Adventure 3 Chelsea Wp
Gender: Men's
Color: Black
Price: $150.00MSRP: $160.00
Rating

Clarks - Morris Easy. Color Black Leather. On sale for $116.95. MSRP $130.00.. 3.0 out of 5 stars

Brand Name: Clarks
Product Name: Morris Easy
Gender: Men's
Color: Black Leather
Price: $116.95MSRP: $130.00
Rating: 3Rated 3 stars out of 5(4)

Martin Dingman - Windsor Waterproof. Color Caramel. Low Stock. On sale for $172.50. MSRP $250.00.. 2.0 out of 5 stars

8 left in stock

Brand Name: Martin Dingman
Product Name: Windsor Waterproof
Gender: Men's
Color: Caramel
Price: $172.50MSRP: $250.00
Rating: 2Rated 2 stars out of 5(1)

Teva - Tusayan Chelsea. Color Chocolate Brown. Low Stock. $149.95. 4.3 out of 5 stars

8 left in stock

Brand Name: Teva
Product Name: Tusayan Chelsea
Gender: Men's
Color: Chocolate Brown
Price: $149.95
Rating: 4Rated 4 stars out of 5(7)

UGG - Biltmore Chelsea. Color Chestnut Suede. $149.95. 4.4 out of 5 stars

Brand Name: UGG
Product Name: Biltmore Chelsea
Gender: Men's
Color: Chestnut Suede
Price: $149.95
Rating: 4Rated 4 stars out of 5(205)

Red Wing Heritage - Weekend Chelsea. Color Copper Rough & Tough Leather. $259.99. 4.1 out of 5 stars

Brand Name: Red Wing Heritage
Product Name: Weekend Chelsea
Gender: Men's
Color: Copper Rough & Tough Leather
Price: $259.99
Rating: 4Rated 4 stars out of 5(21)

Red Wing Heritage - Classic Chelsea. Color Amber Harness. $299.99. 4.8 out of 5 stars

Brand Name: Red Wing Heritage
Product Name: Classic Chelsea
Gender: Men's
Color: Amber Harness
Price: $299.99
Rating: 5Rated 5 stars out of 5(10)

Johnston & Murphy - Upton Chelsea. Color Brown Oiled Full Grain. $169.00. 4.8 out of 5 stars

Brand Name: Johnston & Murphy
Product Name: Upton Chelsea
Gender: Men's
Color: Brown Oiled Full Grain
Price: $169.00
Rating: 5Rated 5 stars out of 5(82)

Dockers - Novato. Color Dark Brown. On sale for $69.99. MSRP $95.00..

Brand Name: Dockers
Product Name: Novato
Gender: Men's
Color: Dark Brown
Price: $69.99MSRP: $95.00
Rating

Ariat - Midtown Rambler. Color Stone. $159.95. 4.5 out of 5 stars

+2 colors/patterns

Brand Name: Ariat
Product Name: Midtown Rambler
Gender: Men's
Color: Stone
Price: $159.95
Rating: 4Rated 4 stars out of 5(257)

Ariat - Sport Booker Ultra. Color Distressed Tan. $149.95. 4.8 out of 5 stars

Brand Name: Ariat
Product Name: Sport Booker Ultra
Gender: Men's
Color: Distressed Tan
Price: $149.95
Rating: 5Rated 5 stars out of 5(480)

Born - Hemlock. Color Black Full Grain. $135.00. 4.3 out of 5 stars

Brand Name: Born
Product Name: Hemlock
Gender: Men's
Color: Black Full Grain
Price: $135.00
Rating: 4Rated 4 stars out of 5(189)

Ariat - Midtown Rambler Boots. Color Matte Black. $159.95. 5.0 out of 5 stars

Brand Name: Ariat
Product Name: Midtown Rambler Boots
Gender: Men's
Color: Matte Black
Price: $159.95
Rating: 5Rated 5 stars out of 5(9)

Deer Stags - Brayden. Color Black. On sale for $59.97. MSRP $100.00.. 3.0 out of 5 stars

Brand Name: Deer Stags
Product Name: Brayden
Gender: Men's
Color: Black
Price: $59.97MSRP: $100.00
Rating: 3Rated 3 stars out of 5(1)

Dansko - Frankie. Color Brown Oiled. $159.95. 4.2 out of 5 stars

Brand Name: Dansko
Product Name: Frankie
Gender: Women's
Color: Brown Oiled
Price: $159.95
Rating: 4Rated 4 stars out of 5(278)

Twisted X - MCA0013. Color Oiled Saddle. $159.95.

Brand Name: Twisted X
Product Name: MCA0013
Gender: Men's
Color: Oiled Saddle
Price: $159.95
Rating

Florsheim - Duke. Color Black Cavello. $149.95. 4.5 out of 5 stars

Brand Name: Florsheim
Product Name: Duke
Gender: Men's
Color: Black Cavello
Price: $149.95
Rating: 5Rated 5 stars out of 5(899)

Ariat - Booker Ultra Square Toe Western Boots. Color Rough Tan. $149.95. 4.7 out of 5 stars

Brown Ariat Booker Ultra Square Toe Western Boots

Brand Name: Ariat
Product Name: Booker Ultra Square Toe Western Boots
Gender: Men's
Color: Rough Tan
Price: $149.95
Rating: 5Rated 5 stars out of 5(44)

Florsheim - Lodge Plain Toe Gore Boot. Color Brown Crazy Horse. $129.95. 4.6 out of 5 stars

Brown Florsheim Lodge Plain Toe Gore Boot

Brand Name: Florsheim
Product Name: Lodge Plain Toe Gore Boot
Gender: Men's
Color: Brown Crazy Horse
Price: $129.95
Rating: 5Rated 5 stars out of 5(96)

Deer Stags - Argos. Color Tan/Blue. On sale for $59.99. MSRP $100.00.. 3.7 out of 5 stars

Brand Name: Deer Stags
Product Name: Argos
Gender: Men's
Color: Tan/Blue
Price: $59.99MSRP: $100.00
Rating: 4Rated 4 stars out of 5(24)

Stacy Adams - Kalen Chelsea Boot. Color Black. $130.00. 4.8 out of 5 stars

Brand Name: Stacy Adams
Product Name: Kalen Chelsea Boot
Gender: Men's
Color: Black
Price: $130.00
Rating: 5Rated 5 stars out of 5(12)

Nunn Bush - 1912 Plain Toe Chelsea Boot. Color Black. On sale for $84.95. MSRP $115.00.. 3.6 out of 5 stars

Black Nunn Bush 1912 Plain Toe Chelsea Boot

Brand Name: Nunn Bush
Product Name: 1912 Plain Toe Chelsea Boot
Gender: Men's
Color: Black
Price: $84.95MSRP: $115.00
Rating: 4Rated 4 stars out of 5(8)

Born - Brody. Color Taupe Dist. $140.00. 4.7 out of 5 stars

Brand Name: Born
Product Name: Brody
Gender: Men's
Color: Taupe Dist
Price: $140.00
Rating: 5Rated 5 stars out of 5(23)

Florsheim - Renegade Plain Toe Gore Boot. Color Cognac. On sale for $127.50. MSRP $150.00.. 4.4 out of 5 stars

Tan Florsheim Renegade Plain Toe Gore Boot

Brand Name: Florsheim
Product Name: Renegade Plain Toe Gore Boot
Gender: Men's
Color: Cognac
Price: $127.50MSRP: $150.00
Rating: 4Rated 4 stars out of 5(19)

Polo Ralph Lauren - Oslo Chelsea. Color Light Beige. On sale for $145.96. MSRP $178.00.. 3.0 out of 5 stars

+2 colors/patterns

Brand Name: Polo Ralph Lauren
Product Name: Oslo Chelsea
Gender: Men's
Color: Light Beige
Price: $145.96MSRP: $178.00
Rating: 3Rated 3 stars out of 5(1)

ECCO - Grainer Chelsea Boot. Color Black. $190.00. 4.8 out of 5 stars

Brand Name: ECCO
Product Name: Grainer Chelsea Boot
Gender: Men's
Color: Black
Price: $190.00
Rating: 5Rated 5 stars out of 5(5)

Nunn Bush - Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology. Color Black Tumbled. On sale for $68.97. MSRP $115.00.. 4.2 out of 5 stars

Black Nunn Bush Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology

Brand Name: Nunn Bush
Product Name: Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Black Tumbled
Price: $68.97MSRP: $115.00
Rating: 4Rated 4 stars out of 5(95)

Johnston & Murphy - Barrett Chelsea. Color Mahogany Full Grain. Low Stock. $185.00. 4.3 out of 5 stars

9 left in stock

Brand Name: Johnston & Murphy
Product Name: Barrett Chelsea
Gender: Men's
Color: Mahogany Full Grain
Price: $185.00
Rating: 4Rated 4 stars out of 5(131)

Florsheim - Rucci Plain Toe Gore Boot. Color Cognac. $139.95. 4.8 out of 5 stars

Brand Name: Florsheim
Product Name: Rucci Plain Toe Gore Boot
Gender: Men's
Color: Cognac
Price: $139.95
Rating: 5Rated 5 stars out of 5(25)

Forsake - Phil Chelsea. Color Black. Low Stock. $145.00.

8 left in stock

Brand Name: Forsake
Product Name: Phil Chelsea
Gender: Men's
Color: Black
Price: $145.00
Rating

Allen Edmonds - Liverpool. Color Black Custom Calf. Low Stock. $495.00. 4.3 out of 5 stars

8 left in stock

Brand Name: Allen Edmonds
Product Name: Liverpool
Gender: Men's
Color: Black Custom Calf
Price: $495.00
Rating: 4Rated 4 stars out of 5(154)

Johnston & Murphy - Kelton Chelsea. Color Black Full Grain. Low Stock. On sale for $139.50. MSRP $155.00.. 3.0 out of 5 stars

5 left in stock

Brand Name: Johnston & Murphy
Product Name: Kelton Chelsea
Gender: Men's
Color: Black Full Grain
Price: $139.50MSRP: $155.00
Rating: 3Rated 3 stars out of 5(1)

Massimo Matteo - Chelsea Classic Boots. Color Black Leather. On sale for $79.75. MSRP $94.95..

Black Massimo Matteo Chelsea Classic Boots

Brand Name: Massimo Matteo
Product Name: Chelsea Classic Boots
Gender: Men's
Color: Black Leather
Price: $79.75MSRP: $94.95
Rating

Johnston & Murphy - XC Flex Raleigh Chelsea. Color Tan Full Grain. $184.95. 4.5 out of 5 stars

Tan Johnston & Murphy XC Flex Raleigh Chelsea

Brand Name: Johnston & Murphy
Product Name: XC Flex Raleigh Chelsea
Gender: Men's
Color: Tan Full Grain
Price: $184.95
Rating: 5Rated 5 stars out of 5(50)

Birkenstock - Highwood Deep Blue. Color Chocolate. $210.00. 4.0 out of 5 stars

Brand Name: Birkenstock
Product Name: Highwood Deep Blue
Gender: Men's
Color: Chocolate
Price: $210.00
Rating: 4Rated 4 stars out of 5(1)

Bogs - Classic Casual Chelsea II. Color Black. On sale for $104.22. MSRP $150.00.. 4.6 out of 5 stars

Brand Name: Bogs
Product Name: Classic Casual Chelsea II
Gender: Men's
Color: Black
Price: $104.22MSRP: $150.00
Rating: 5Rated 5 stars out of 5(8)

Stacy Adams - Martindale Chukka Boot. Color Bordeaux. On sale for $97.50. MSRP $130.00.. 4.0 out of 5 stars

Burgundy Stacy Adams Martindale Chukka Boot

Brand Name: Stacy Adams
Product Name: Martindale Chukka Boot
Gender: Men's
Color: Bordeaux
Price: $97.50MSRP: $130.00
Rating: 4Rated 4 stars out of 5(1)

Thomas & Vine - Jaylon. Color Black. Low Stock. On sale for $95.18. MSRP $169.99.. 3.0 out of 5 stars

9 left in stock

Brand Name: Thomas & Vine
Product Name: Jaylon
Gender: Men's
Color: Black
Price: $95.18MSRP: $169.99
Rating: 3Rated 3 stars out of 5(1)

Ariat - Hybrid Low Western Boot. Color Stone. $159.95. 4.6 out of 5 stars

Brand Name: Ariat
Product Name: Hybrid Low Western Boot
Gender: Men's
Color: Stone
Price: $159.95
Rating: 5Rated 5 stars out of 5(66)

Thomas & Vine - Oswald. Color Black. Low Stock. On sale for $101.22. MSRP $169.99.. 3.0 out of 5 stars

6 left in stock

Brand Name: Thomas & Vine
Product Name: Oswald
Gender: Men's
Color: Black
Price: $101.22MSRP: $169.99
Rating: 3Rated 3 stars out of 5(1)

COACH - Dalton Chelsea Boot. Color Dark Saddle. $295.00. 1.0 out of 5 stars

Brand Name: COACH
Product Name: Dalton Chelsea Boot
Gender: Men's
Color: Dark Saddle
Price: $295.00
Rating: 1Rated 1 star out of 5(1)

XTRATUF - Leather Ankle Deck Boot. Color Black. Low Stock. On sale for $78.93. MSRP $155.00.. 4.1 out of 5 stars

3 left in stock

Brand Name: XTRATUF
Product Name: Leather Ankle Deck Boot
Gender: Men's
Color: Black
Price: $78.93MSRP: $155.00
Rating: 4Rated 4 stars out of 5(17)

Vince - Erik. Color Black. Low Stock. On sale for $395.00. MSRP $450.00..

9 left in stock

Brand Name: Vince
Product Name: Erik
Gender: Men's
Color: Black
Price: $395.00MSRP: $450.00
Rating

Columbia - Landroamer™ Scout. Color Espresso II/Warp Red. $119.95. 4.3 out of 5 stars

Brand Name: Columbia
Product Name: Landroamer™ Scout
Gender: Men's
Color: Espresso II/Warp Red
Price: $119.95
Rating: 4Rated 4 stars out of 5(20)

Twisted X - MHKB003. Color Distressed Saddle/Saddle. $159.95.

Brand Name: Twisted X
Product Name: MHKB003
Gender: Men's
Color: Distressed Saddle/Saddle
Price: $159.95
Rating

Marc Joseph New York - Austin. Color Cognac Grainy. On sale for $89.95. MSRP $195.00.. 5.0 out of 5 stars

Brand Name: Marc Joseph New York
Product Name: Austin
Gender: Men's
Color: Cognac Grainy
Price: $89.95MSRP: $195.00
Rating: 5Rated 5 stars out of 5(5)

Steve Madden - Sverne. Color Tan Leather. On sale for $126.99. MSRP $150.00.. 3.0 out of 5 stars

Brand Name: Steve Madden
Product Name: Sverne
Gender: Men's
Color: Tan Leather
Price: $126.99MSRP: $150.00
Rating: 3Rated 3 stars out of 5(1)

UGG - Burleigh Chelsea. Color Chestnut. $169.95. 4.5 out of 5 stars

Brand Name: UGG
Product Name: Burleigh Chelsea
Gender: Men's
Color: Chestnut
Price: $169.95
Rating: 5Rated 5 stars out of 5(16)

Ariat - Booker Ultra Western Boots. Color Charro Tan. $149.95. 4.8 out of 5 stars

Brand Name: Ariat
Product Name: Booker Ultra Western Boots
Gender: Men's
Color: Charro Tan
Price: $149.95
Rating: 5Rated 5 stars out of 5(205)

Eastland 1955 Edition - Daily Double. Color Tan. Low Stock. On sale for $97.50. MSRP $125.00.. 3.5 out of 5 stars

9 left in stock

Brand Name: Eastland 1955 Edition
Product Name: Daily Double
Gender: Men's
Color: Tan
Price: $97.50MSRP: $125.00
Rating: 4Rated 4 stars out of 5(12)

Vince Camuto - Firat Chelsea Boot. Color Black. Low Stock. $169.00.

4 left in stock

Brand Name: Vince Camuto
Product Name: Firat Chelsea Boot
Gender: Men's
Color: Black
Price: $169.00
Rating

Stacy Adams - Finney Cap Toe Chelsea Boot. Color Brown Multi. Low Stock. On sale for $127.60. MSRP $145.00.. 4.3 out of 5 stars

5 left in stock

Brown Stacy Adams Finney Cap Toe Chelsea Boot

Brand Name: Stacy Adams
Product Name: Finney Cap Toe Chelsea Boot
Gender: Men's
Color: Brown Multi
Price: $127.60MSRP: $145.00
Rating: 4Rated 4 stars out of 5(3)

Steve Madden - Hawke. Color Black/Grey. Low Stock. On sale for $128.05. MSRP $170.00.. 5.0 out of 5 stars

9 left in stock

Brand Name: Steve Madden
Product Name: Hawke
Gender: Men's
Color: Black/Grey
Price: $128.05MSRP: $170.00
Rating: 5Rated 5 stars out of 5(1)

Roper - Clearcut Romeo. Color Tan. Low Stock. On sale for $54.97. MSRP $100.00.. 4.0 out of 5 stars

1 left in stock

+2 colors/patterns

Brand Name: Roper
Product Name: Clearcut Romeo
Gender: Men's
Color: Tan
Price: $54.97MSRP: $100.00
Rating: 4Rated 4 stars out of 5(1)

Vince - Tamas. Color Coastal. Low Stock. On sale for $192.50. MSRP $275.00..

4 left in stock

Brand Name: Vince
Product Name: Tamas
Gender: Men's
Color: Coastal
Price: $192.50MSRP: $275.00
Rating

SeaVees - Ballard Boot. Color Stone. On sale for $106.32. MSRP $110.00..

Brand Name: SeaVees
Product Name: Ballard Boot
Gender: Men's
Color: Stone
Price: $106.32MSRP: $110.00
Rating

SOREL - Hi-Line™ Chelsea. Color Black/Jet. Low Stock. On sale for $89.97. MSRP $175.00.. 4.6 out of 5 stars

1 left in stock

Brand Name: SOREL
Product Name: Hi-Line™ Chelsea
Gender: Men's
Color: Black/Jet
Price: $89.97MSRP: $175.00
Rating: 5Rated 5 stars out of 5(49)

Stacy Adams - Gabriel Chelsea Boot. Color Black Suede. $119.99. 4.6 out of 5 stars

Brand Name: Stacy Adams
Product Name: Gabriel Chelsea Boot
Gender: Men's
Color: Black Suede
Price: $119.99
Rating: 5Rated 5 stars out of 5(8)

Johnston & Murphy Collection - Hartley Chelsea. Color Black Italian Calfskin. On sale for $221.00. MSRP $325.00..

Black Johnston & Murphy Collection Hartley Chelsea

Brand Name: Johnston & Murphy Collection
Product Name: Hartley Chelsea
Gender: Men's
Color: Black Italian Calfskin
Price: $221.00MSRP: $325.00
Rating

Steve Madden - Highline. Color Chocolate Brown Suede. $100.00. 4.1 out of 5 stars

Brand Name: Steve Madden
Product Name: Highline
Gender: Men's
Color: Chocolate Brown Suede
Price: $100.00
Rating: 4Rated 4 stars out of 5(21)

ECCO - Track 25 Hydromax Water Resistant Chelsea Boot. Color Cocoa Brown Nubuck. On sale for $119.99. MSRP $200.00.. 5.0 out of 5 stars

Brown ECCO Track 25 Hydromax Water Resistant Chelsea Boot

Brand Name: ECCO
Product Name: Track 25 Hydromax Water Resistant Chelsea Boot
Gender: Men's
Color: Cocoa Brown Nubuck
Price: $119.99MSRP: $200.00
Rating: 5Rated 5 stars out of 5(2)

Roper - Gum Sticker Romeo. Color Tan. $116.99.

Brand Name: Roper
Product Name: Gum Sticker Romeo
Gender: Men's
Color: Tan
Price: $116.99
Rating

Steve Madden - Huston. Color Brown Suede. On sale for $115.73. MSRP $150.00..

Brand Name: Steve Madden
Product Name: Huston
Gender: Men's
Color: Brown Suede
Price: $115.73MSRP: $150.00
Rating

Dockers - Novi. Color Dark Brown. On sale for $50.34. MSRP $85.00..

Brand Name: Dockers
Product Name: Novi
Gender: Men's
Color: Dark Brown
Price: $50.34MSRP: $85.00
Rating

Deer Stags - Rockland. Color Black/Black. On sale for $60.00. MSRP $100.00.. 3.6 out of 5 stars

Brand Name: Deer Stags
Product Name: Rockland
Gender: Men's
Color: Black/Black
Price: $60.00MSRP: $100.00
Rating: 4Rated 4 stars out of 5(29)

Dockers - Townsend. Color Black. On sale for $59.99. MSRP $85.00..

Brand Name: Dockers
Product Name: Townsend
Gender: Men's
Color: Black
Price: $59.99MSRP: $85.00
Rating

Dockers - Durham. Color Black. On sale for $51.42. MSRP $85.00..

Brand Name: Dockers
Product Name: Durham
Gender: Men's
Color: Black
Price: $51.42MSRP: $85.00
Rating

L.L.Bean - Wellie Sport Rubber Chelsea. Color Dark Cocoa. Low Stock. On sale for $79.99. MSRP $109.00.. 3.7 out of 5 stars

5 left in stock

Brown L.L.Bean Wellie Sport Rubber Chelsea

Brand Name: L.L.Bean
Product Name: Wellie Sport Rubber Chelsea
Gender: Men's
Color: Dark Cocoa
Price: $79.99MSRP: $109.00
Rating: 4Rated 4 stars out of 5(22)

Vance Co. - Landon Chelsea Dress Boot. Color Chestnut Faux Leather. Low Stock. On sale for $60.99. MSRP $69.99.. 4.2 out of 5 stars

5 left in stock

Unknown Color Vance Co. Landon Chelsea Dress Boot

Brand Name: Vance Co.
Product Name: Landon Chelsea Dress Boot
Gender: Men's
Color: Chestnut Faux Leather
Price: $60.99MSRP: $69.99
Rating: 4Rated 4 stars out of 5(29)

Dockers - Ransom. Color Dark Brown. On sale for $59.99. MSRP $80.00.. 2.0 out of 5 stars

Brand Name: Dockers
Product Name: Ransom
Gender: Men's
Color: Dark Brown
Price: $59.99MSRP: $80.00
Rating: 2Rated 2 stars out of 5(1)

Vance Co. - Garrett Cap Toe Chelsea Boot. Color Tan Man-made. Low Stock. On sale for $59.99. MSRP $69.99.. 3.2 out of 5 stars

7 left in stock

Unknown Color Vance Co. Garrett Cap Toe Chelsea Boot

Brand Name: Vance Co.
Product Name: Garrett Cap Toe Chelsea Boot
Gender: Men's
Color: Tan Man-made
Price: $59.99MSRP: $69.99
Rating: 3Rated 3 stars out of 5(10)

Dockers - Brookside. Color Cognac. On sale for $59.99. MSRP $85.00..

Brand Name: Dockers
Product Name: Brookside
Gender: Men's
Color: Cognac
Price: $59.99MSRP: $85.00
Rating

Size 8.5 Ankle Chelsea Boots

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