Skip to search results Skip to filters Skip to sort Skip to selected filters

Men's Ankle Dress Products

50 items found

Sort By

Your Selections

Search Results

. Florsheim - Midtown Plain Toe Zipper Boot. Color Brown Smooth. On sale for $128.34. MSRP $135.00. 5% off. 4.6 out of 5 stars

Brown Florsheim Midtown Plain Toe Zipper Boot

Brown Florsheim Midtown Plain Toe Zipper Boot

+1

Brand Name: Florsheim
Product Name: Midtown Plain Toe Zipper Boot
Gender: Men's
Color: Brown Smooth
Price: $128.34MSRP: $135.005% OFF
Rating: 5Rated 5 stars out of 5(507)

Clarks - Shepton. Color Beeswax Leather. On sale for $65.45. MSRP $100.00. 35% off. 2.0 out of 5 stars

Brown Clarks Shepton

Brown Clarks Shepton

+5

Brand Name: Clarks
Product Name: Shepton
Gender: Men's
Color: Beeswax Leather
Price: $65.45MSRP: $100.0035% OFF
Rating: 2Rated 2 stars out of 5(4)

Stacy Adams - Madison Boot. Color Black. On sale for $139.95. MSRP $149.95. 7% off. 4.6 out of 5 stars

Black Stacy Adams Madison Boot

Brand Name: Stacy Adams
Product Name: Madison Boot
Gender: Men's
Color: Black
Price: $139.95MSRP: $149.957% OFF
Rating: 5Rated 5 stars out of 5(871)

Florsheim - Lodge Cap Toe Lace-Up Boot. Color Brown Crazy Horse. On sale for $99.95. MSRP $140.00. 29% off. 4.6 out of 5 stars

Brown Florsheim Lodge Cap Toe Lace-Up Boot

Brown Florsheim Lodge Cap Toe Lace-Up Boot

+3

Brand Name: Florsheim
Product Name: Lodge Cap Toe Lace-Up Boot
Gender: Men's
Color: Brown Crazy Horse
Price: $99.95MSRP: $140.0029% OFF
Rating: 5Rated 5 stars out of 5(168)

Dr. Martens - 8053 Platform. Color Black. On sale for $144.95. MSRP $180.00. 19% off. 3.3 out of 5 stars

Black Dr. Martens 8053 Platform

Black Dr. Martens 8053 Platform

Brand Name: Dr. Martens
Product Name: 8053 Platform
Gender: Unisex
Color: Black
Price: $144.95MSRP: $180.0019% OFF
Rating: 3Rated 3 stars out of 5(11)

Nunn Bush - Odell 2.0 Wingtip Dress Casual Chukka Leather Boot. Color Black. On sale for $68.85. MSRP $109.95. 37% off. 4.4 out of 5 stars

Black Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boot

Black Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boot

+1

Brand Name: Nunn Bush
Product Name: Odell 2.0 Wingtip Dress Casual Chukka Leather Boot
Gender: Men's
Color: Black
Price: $68.85MSRP: $109.9537% OFF
Rating: 4Rated 4 stars out of 5(7)

Vance Co. - Garrett Cap Toe Chelsea Boot. Color Tan Man-made. Low Stock. On sale for $63.00. MSRP $69.99. 10% off. 3.1 out of 5 stars

Low Stock

Brown Vance Co. Garrett Cap Toe Chelsea Boot

Brown Vance Co. Garrett Cap Toe Chelsea Boot

+2

Brand Name: Vance Co.
Product Name: Garrett Cap Toe Chelsea Boot
Gender: Men's
Color: Tan Man-made
Price: $63.00MSRP: $69.9910% OFF
Rating: 3Rated 3 stars out of 5(11)

Tommy Hilfiger - Rosell. Color Medium Brown. On sale for $43.53. MSRP $79.95. 46% off.

Brown Tommy Hilfiger Rosell

Brown Tommy Hilfiger Rosell

+1

Brand Name: Tommy Hilfiger
Product Name: Rosell
Gender: Men's
Color: Medium Brown
Price: $43.53MSRP: $79.9546% OFF
Rating

Johnston & Murphy Collection - Dudley Lug Zip Boot. Color Brown Waxed English Suede. On sale for $199.00. MSRP $285.00. 30% off.

Brown Johnston & Murphy Collection Dudley Lug Zip Boot

Brown Johnston & Murphy Collection Dudley Lug Zip Boot

Brand Name: Johnston & Murphy Collection
Product Name: Dudley Lug Zip Boot
Gender: Men's
Color: Brown Waxed English Suede
Price: $199.00MSRP: $285.0030% OFF
Rating

Deer Stags - Bangor. Color Black/Black. On sale for $48.00. MSRP $100.00. 52% off. 3.9 out of 5 stars

Black Deer Stags Bangor

Black Deer Stags Bangor

+2

Brand Name: Deer Stags
Product Name: Bangor
Gender: Men's
Color: Black/Black
Price: $48.00MSRP: $100.0052% OFF
Rating: 4Rated 4 stars out of 5(14)

Dr. Martens - Jadon Leather Lace-Up Boots. Color Charcoal Grey. On sale for $127.96. MSRP $200.00. 36% off. 5.0 out of 5 stars

Gray Dr. Martens Jadon Leather Lace-Up Boots

Gray Dr. Martens Jadon Leather Lace-Up Boots

Brand Name: Dr. Martens
Product Name: Jadon Leather Lace-Up Boots
Gender: Unisex
Color: Charcoal Grey
Price: $127.96MSRP: $200.0036% OFF
Rating: 5Rated 5 stars out of 5(1)

Stacy Adams - Martindale Chukka Boot. Color Bordeaux. On sale for $97.50. MSRP $130.00. 25% off. 4.0 out of 5 stars

Burgundy Stacy Adams Martindale Chukka Boot

Burgundy Stacy Adams Martindale Chukka Boot

Brand Name: Stacy Adams
Product Name: Martindale Chukka Boot
Gender: Men's
Color: Bordeaux
Price: $97.50MSRP: $130.0025% OFF
Rating: 4Rated 4 stars out of 5(1)

Stacy Adams - Maxwell Plain Toe Demi Boot. Color Black. On sale for $112.50. MSRP $125.00. 10% off. 4.7 out of 5 stars

Black Stacy Adams Maxwell Plain Toe Demi Boot

Black Stacy Adams Maxwell Plain Toe Demi Boot

+2

Brand Name: Stacy Adams
Product Name: Maxwell Plain Toe Demi Boot
Gender: Men's
Color: Black
Price: $112.50MSRP: $125.0010% OFF
Rating: 5Rated 5 stars out of 5(43)

Florsheim - Rucci Wingtip Lace Boot. Color Cognac. $138.95. 5.0 out of 5 stars

Tan Florsheim Rucci Wingtip Lace Boot

Tan Florsheim Rucci Wingtip Lace Boot

+2

Brand Name: Florsheim
Product Name: Rucci Wingtip Lace Boot
Gender: Men's
Color: Cognac
Price: $138.95
Rating: 5Rated 5 stars out of 5(7)

Florsheim - Duke. Color Black Cavello. On sale for $143.31. MSRP $150.00. 4% off. 4.5 out of 5 stars

Black Florsheim Duke

Black Florsheim Duke

+2

Brand Name: Florsheim
Product Name: Duke
Gender: Men's
Color: Black Cavello
Price: $143.31MSRP: $150.004% OFF
Rating: 5Rated 5 stars out of 5(936)

. Florsheim - Norwalk Side Zip Boot. Color Brown Crazy Horse. On sale for $146.34. MSRP $150.00. 2% off. 4.5 out of 5 stars

Brown Florsheim Norwalk Side Zip Boot

Brown Florsheim Norwalk Side Zip Boot

+2

Brand Name: Florsheim
Product Name: Norwalk Side Zip Boot
Gender: Men's
Color: Brown Crazy Horse
Price: $146.34MSRP: $150.002% OFF
Rating: 4Rated 4 stars out of 5(112)

Eastland 1955 Edition - Norway. Color Oak. On sale for $52.50. MSRP $125.00. 58% off.

Brown Eastland 1955 Edition Norway

Brown Eastland 1955 Edition Norway

+2

Brand Name: Eastland 1955 Edition
Product Name: Norway
Gender: Men's
Color: Oak
Price: $52.50MSRP: $125.0058% OFF
Rating

Dockers - Esmond. Color Cognac. Low Stock. On sale for $59.99. MSRP $85.00. 29% off.

Low Stock

Tan Dockers Esmond

Tan Dockers Esmond

+4

Brand Name: Dockers
Product Name: Esmond
Gender: Men's
Color: Cognac
Price: $59.99MSRP: $85.0029% OFF
Rating

Mephisto - Ladislas. Color Walnut Distressed. Low Stock. On sale for $347.13. MSRP $399.00. 13% off.

Low Stock

Olive Mephisto Ladislas

Olive Mephisto Ladislas

Brand Name: Mephisto
Product Name: Ladislas
Gender: Men's
Color: Walnut Distressed
Price: $347.13MSRP: $399.0013% OFF
Rating

Calvin Klein - Donto. Color Black Leather. Low Stock. On sale for $87.35. MSRP $150.00. 42% off.

Low Stock

Black Calvin Klein Donto

Black Calvin Klein Donto

+2

Brand Name: Calvin Klein
Product Name: Donto
Gender: Men's
Color: Black Leather
Price: $87.35MSRP: $150.0042% OFF
Rating

Josef Seibel - Erroll 52 Boots. Color Black. On sale for $148.75. MSRP $175.00. 15% off. 5.0 out of 5 stars

Black Josef Seibel Erroll 52 Boots

Black Josef Seibel Erroll 52 Boots

+2

Brand Name: Josef Seibel
Product Name: Erroll 52 Boots
Gender: Men's
Color: Black
Price: $148.75MSRP: $175.0015% OFF
Rating: 5Rated 5 stars out of 5(1)

Naot - Commander. Color Seal Brown Suede. On sale for $199.15. MSRP $239.95. 17% off.

Brown Naot Commander

Brown Naot Commander

+2

Brand Name: Naot
Product Name: Commander
Gender: Men's
Color: Seal Brown Suede
Price: $199.15MSRP: $239.9517% OFF
Rating

Vance Co. - Alex Chelsea Boot. Color Grey Faux Leather. Low Stock. On sale for $60.59. MSRP $64.99. 7% off. 3.7 out of 5 stars

Low Stock

Gray Vance Co. Alex Chelsea Boot

Gray Vance Co. Alex Chelsea Boot

+3

Brand Name: Vance Co.
Product Name: Alex Chelsea Boot
Gender: Men's
Color: Grey Faux Leather
Price: $60.59MSRP: $64.997% OFF
Rating: 4Rated 4 stars out of 5(34)

Johnston & Murphy - Connelly Wing Tip Boot. Color Black Full Grain. Low Stock. On sale for $179.10. MSRP $199.00. 10% off. 3.2 out of 5 stars

Low Stock

Black Johnston & Murphy Connelly Wing Tip Boot

Black Johnston & Murphy Connelly Wing Tip Boot

Brand Name: Johnston & Murphy
Product Name: Connelly Wing Tip Boot
Gender: Men's
Color: Black Full Grain
Price: $179.10MSRP: $199.0010% OFF
Rating: 3Rated 3 stars out of 5(58)

Born - Ryker. Color Dark Grey. On sale for $99.40. MSRP $140.00. 29% off.

Gray Born Ryker

Gray Born Ryker

+3

Brand Name: Born
Product Name: Ryker
Gender: Men's
Color: Dark Grey
Price: $99.40MSRP: $140.0029% OFF
Rating

Dr. Martens - 101 Unbound Leather Ankle Boot. Color Black. On sale for $139.95. MSRP $160.00. 13% off. 4.7 out of 5 stars

Black Dr. Martens 101 Unbound Leather Ankle Boot

Black Dr. Martens 101 Unbound Leather Ankle Boot

+2

Brand Name: Dr. Martens
Product Name: 101 Unbound Leather Ankle Boot
Gender: Unisex
Color: Black
Price: $139.95MSRP: $160.0013% OFF
Rating: 5Rated 5 stars out of 5(3)

COACH - Caiden Boot. Color Black. Low Stock. On sale for $165.83. MSRP $295.00. 44% off.

Low Stock

Black COACH Caiden Boot

Black COACH Caiden Boot

+2

Brand Name: COACH
Product Name: Caiden Boot
Gender: Men's
Color: Black
Price: $165.83MSRP: $295.0044% OFF
Rating

Johnston & Murphy - Braydon Chelsea Boots. Color Brown Oiled Full Grain. Low Stock. On sale for $126.75. MSRP $149.00. 15% off.

Low Stock

Brown Johnston & Murphy Braydon Chelsea Boots

Brown Johnston & Murphy Braydon Chelsea Boots

Brand Name: Johnston & Murphy
Product Name: Braydon Chelsea Boots
Gender: Men's
Color: Brown Oiled Full Grain
Price: $126.75MSRP: $149.0015% OFF
Rating

Johnston & Murphy - Lewis Zip Boot. Color Black Full Grain. Low Stock. On sale for $99.99. MSRP $129.90. 23% off. 4.4 out of 5 stars

Low Stock

Black Johnston & Murphy Lewis Zip Boot

Black Johnston & Murphy Lewis Zip Boot

Brand Name: Johnston & Murphy
Product Name: Lewis Zip Boot
Gender: Men's
Color: Black Full Grain
Price: $99.99MSRP: $129.9023% OFF
Rating: 4Rated 4 stars out of 5(35)

Magnanni - Loda. Color Navy Suede. Low Stock. On sale for $319.50. MSRP $450.00. 29% off.

Low Stock

Blue Magnanni Loda

Blue Magnanni Loda

Brand Name: Magnanni
Product Name: Loda
Gender: Men's
Color: Navy Suede
Price: $319.50MSRP: $450.0029% OFF
Rating

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Tan CH. Low Stock. On sale for $85.10. MSRP $115.00. 26% off. 4.3 out of 5 stars

Low Stock

Brown Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Brown Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

+3

Brand Name: Nunn Bush
Product Name: Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Tan CH
Price: $85.10MSRP: $115.0026% OFF
Rating: 4Rated 4 stars out of 5(133)

Dr. Scholl's - Russell. Color Black Faux Leather. On sale for $76.50. MSRP $85.00. 10% off.

Black Dr. Scholl's Russell

Black Dr. Scholl's Russell

Brand Name: Dr. Scholl's
Product Name: Russell
Gender: Men's
Color: Black Faux Leather
Price: $76.50MSRP: $85.0010% OFF
Rating

Nunn Bush - Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology. Color Brown CH. On sale for $98.90. MSRP $115.00. 14% off. 4.2 out of 5 stars

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

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

+3

Brand Name: Nunn Bush
Product Name: Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Brown CH
Price: $98.90MSRP: $115.0014% OFF
Rating: 4Rated 4 stars out of 5(102)

SOREL - Scout 87'™ Lux Waterproof. Color Black/Black. Low Stock. On sale for $179.95. MSRP $200.00. 10% off.

Low Stock

Black SOREL Scout 87'™ Lux Waterproof

Black SOREL Scout 87'™ Lux Waterproof

+2

Brand Name: SOREL
Product Name: Scout 87'™ Lux Waterproof
Gender: Men's
Color: Black/Black
Price: $179.95MSRP: $200.0010% OFF
Rating

Dr. Martens - 2976 Warmwair Grizzly Leather Chelsea Boots. Color Black. On sale for $144.00. MSRP $180.00. 20% off. 3.5 out of 5 stars

Black Dr. Martens 2976 Warmwair Grizzly Leather Chelsea Boots

Black Dr. Martens 2976 Warmwair Grizzly Leather Chelsea Boots

+2

Brand Name: Dr. Martens
Product Name: 2976 Warmwair Grizzly Leather Chelsea Boots
Gender: Unisex
Color: Black
Price: $144.00MSRP: $180.0020% OFF
Rating: 4Rated 4 stars out of 5(2)

Hunter - Orford. Color Dark Brown. On sale for $161.95. MSRP $180.00. 10% off. 5.0 out of 5 stars

Brown Hunter Orford

Brown Hunter Orford

+5

Brand Name: Hunter
Product Name: Orford
Gender: Men's
Color: Dark Brown
Price: $161.95MSRP: $180.0010% OFF
Rating: 5Rated 5 stars out of 5(2)

Tommy Hilfiger - Risten. Color Brown. Low Stock. On sale for $53.56. MSRP $79.95. 33% off.

Low Stock

Brown Tommy Hilfiger Risten

Brown Tommy Hilfiger Risten

Brand Name: Tommy Hilfiger
Product Name: Risten
Gender: Men's
Color: Brown
Price: $53.56MSRP: $79.9533% OFF
Rating

Dockers - Ettrick. Color Black. Low Stock. On sale for $53.28. MSRP $85.00. 37% off.

Low Stock

Black Dockers Ettrick

Black Dockers Ettrick

+2

Brand Name: Dockers
Product Name: Ettrick
Gender: Men's
Color: Black
Price: $53.28MSRP: $85.0037% OFF
Rating

Clarks - Whiddon Zip. Color Waterproof Black Leather. Low Stock. On sale for $54.99. MSRP $120.00. 54% off. 3.3 out of 5 stars

Low Stock

Black Clarks Whiddon Zip

Black Clarks Whiddon Zip

Brand Name: Clarks
Product Name: Whiddon Zip
Gender: Men's
Color: Waterproof Black Leather
Price: $54.99MSRP: $120.0054% OFF
Rating: 3Rated 3 stars out of 5(15)

Dr. Martens - Bonny Tech Winter Extreme Lace-Up Boots. Color Black. On sale for $113.35. MSRP $140.00. 19% off. 3.0 out of 5 stars

Black Dr. Martens Bonny Tech Winter Extreme Lace-Up Boots

Black Dr. Martens Bonny Tech Winter Extreme Lace-Up Boots

Brand Name: Dr. Martens
Product Name: Bonny Tech Winter Extreme Lace-Up Boots
Gender: Unisex
Color: Black
Price: $113.35MSRP: $140.0019% OFF
Rating: 3Rated 3 stars out of 5(2)

Tommy Hilfiger - Tarlin. Color Brown. Low Stock. On sale for $66.43. MSRP $119.00. 44% off.

Low Stock

Brown Tommy Hilfiger Tarlin

Brown Tommy Hilfiger Tarlin

+3

Brand Name: Tommy Hilfiger
Product Name: Tarlin
Gender: Men's
Color: Brown
Price: $66.43MSRP: $119.0044% OFF
Rating

Clarks - Gravelle Top. Color Brown Leather. Low Stock. On sale for $86.97. MSRP $160.00. 46% off. 2.0 out of 5 stars

Low Stock

Brown Clarks Gravelle Top

Brown Clarks Gravelle Top

Brand Name: Clarks
Product Name: Gravelle Top
Gender: Men's
Color: Brown Leather
Price: $86.97MSRP: $160.0046% OFF
Rating: 2Rated 2 stars out of 5(4)

Roper - Gumsticker Romeo. Color Brown. On sale for $83.78. MSRP $126.99. 34% off.

Brown Roper Gumsticker Romeo

Brown Roper Gumsticker Romeo

Brand Name: Roper
Product Name: Gumsticker Romeo
Gender: Men's
Color: Brown
Price: $83.78MSRP: $126.9934% OFF
Rating

Martin Dingman - McKinley Wingtip Boot. Color Oak. On sale for $284.40. MSRP $395.00. 28% off.

Brown Martin Dingman McKinley Wingtip Boot

Brown Martin Dingman McKinley Wingtip Boot

+2

Brand Name: Martin Dingman
Product Name: McKinley Wingtip Boot
Gender: Men's
Color: Oak
Price: $284.40MSRP: $395.0028% OFF
Rating

Martin Dingman - McKinley Boot. Color Khaki. Low Stock. On sale for $332.50. MSRP $350.00. 5% off. 2.0 out of 5 stars

Low Stock

Khaki Martin Dingman McKinley Boot

Khaki Martin Dingman McKinley Boot

+2

Brand Name: Martin Dingman
Product Name: McKinley Boot
Gender: Men's
Color: Khaki
Price: $332.50MSRP: $350.005% OFF
Rating: 2Rated 2 stars out of 5(1)

Kamik - Atwater. Color Black. Low Stock. On sale for $89.93. MSRP $119.99. 25% off. 5.0 out of 5 stars

Low Stock

Black Kamik Atwater

Black Kamik Atwater

+2

Brand Name: Kamik
Product Name: Atwater
Gender: Men's
Color: Black
Price: $89.93MSRP: $119.9925% OFF
Rating: 5Rated 5 stars out of 5(1)

Martin Dingman - Morgan. Color Chocolate. Low Stock. On sale for $315.00. MSRP $350.00. 10% off.

Low Stock

Brown Martin Dingman Morgan

Brown Martin Dingman Morgan

Brand Name: Martin Dingman
Product Name: Morgan
Gender: Men's
Color: Chocolate
Price: $315.00MSRP: $350.0010% OFF
Rating

Carlos by Carlos Santana - Mantra Chelsea Boot. Color Black Calfskin Leather. Low Stock. On sale for $104.29. MSRP $128.95. 19% off. 4.1 out of 5 stars

Low Stock

Black Carlos by Carlos Santana Mantra Chelsea Boot

Black Carlos by Carlos Santana Mantra Chelsea Boot

Brand Name: Carlos by Carlos Santana
Product Name: Mantra Chelsea Boot
Gender: Men's
Color: Black Calfskin Leather
Price: $104.29MSRP: $128.9519% OFF
Rating: 4Rated 4 stars out of 5(31)

Milwaukee Boot Company - Clybourn Chelsea Boot. Color Black. Low Stock. On sale for $214.65. MSRP $265.00. 19% off. 4.2 out of 5 stars

Low Stock

Black Milwaukee Boot Company Clybourn Chelsea Boot

Black Milwaukee Boot Company Clybourn Chelsea Boot

+2

Brand Name: Milwaukee Boot Company
Product Name: Clybourn Chelsea Boot
Gender: Men's
Color: Black
Price: $214.65MSRP: $265.0019% OFF
Rating: 4Rated 4 stars out of 5(10)

Penny Luck - Gambler Boot. Color Pecan Brown. Low Stock. On sale for $237.32. MSRP $349.00. 32% off. 4.6 out of 5 stars

Low Stock

Brown Penny Luck Gambler Boot

Brown Penny Luck Gambler Boot

+2

Brand Name: Penny Luck
Product Name: Gambler Boot
Gender: Men's
Color: Pecan Brown
Price: $237.32MSRP: $349.0032% OFF
Rating: 5Rated 5 stars out of 5(18)

Join Our List, Get 10% Off

Sign up for Zappos emails—new subscribers get 10% off a future order!* Plus, get early access to sales, coupons, and more. (One code per email address.)