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

Size 8.5 Medium Size Square Toe On Sale Products

47 items found

Sort By

Your Selections

Search Results

Nunn Bush - Jarvis Moccasin Toe Slip-On Dress Casual Business Loafers. Color Cognac. On sale for $59.95. MSRP $90.00. 33% off. 3.7 out of 5 stars

Tan Nunn Bush Jarvis Moccasin Toe Slip-On Dress Casual Business Loafers

Tan Nunn Bush Jarvis Moccasin Toe Slip-On Dress Casual Business Loafers

+2

Brand Name: Nunn Bush
Product Name: Jarvis Moccasin Toe Slip-On Dress Casual Business Loafers
Gender: Men's
Color: Cognac
Price: $59.95MSRP: $90.0033% OFF
Rating: 4Rated 4 stars out of 5(3)

Rockport - Style Leader 2 Bike Toe Oxford. Color Black Waxed Calf. On sale for $99.95. MSRP $129.95. 23% off. 4.5 out of 5 stars

Black Rockport Style Leader 2 Bike Toe Oxford

Black Rockport Style Leader 2 Bike Toe Oxford

+1

Brand Name: Rockport
Product Name: Style Leader 2 Bike Toe Oxford
Gender: Men's
Color: Black Waxed Calf
Price: $99.95MSRP: $129.9523% OFF
Rating: 4Rated 4 stars out of 5(333)

Born - Marcel. Color Taupe. Low Stock. On sale for $99.00. MSRP $110.00. 10% off. 3.5 out of 5 stars

Low Stock

Taupe Born Marcel

Taupe Born Marcel

+7

Brand Name: Born
Product Name: Marcel
Gender: Men's
Color: Taupe
Price: $99.00MSRP: $110.0010% OFF
Rating: 4Rated 4 stars out of 5(4)

Florsheim - Jackson Cap Toe Oxford. Color Cognac. On sale for $89.95. MSRP $120.00. 25% off. 4.5 out of 5 stars

Tan Florsheim Jackson Cap Toe Oxford

Tan Florsheim Jackson Cap Toe Oxford

+2

Brand Name: Florsheim
Product Name: Jackson Cap Toe Oxford
Gender: Men's
Color: Cognac
Price: $89.95MSRP: $120.0025% OFF
Rating: 5Rated 5 stars out of 5(51)

TOMS - Classic Alpargata. Color Navy. On sale for $46.88. MSRP $50.00. 6% off. 4.3 out of 5 stars

Navy TOMS Classic Alpargata

Navy TOMS Classic Alpargata

+4

Brand Name: TOMS
Product Name: Classic Alpargata
Gender: Men's
Color: Navy
Price: $46.88MSRP: $50.006% OFF
Rating: 4Rated 4 stars out of 5(155)

Clarks - DressLite Ace. Color Black. On sale for $73.50. MSRP $105.00. 30% off.

Black Clarks DressLite Ace

Black Clarks DressLite Ace

+2

Brand Name: Clarks
Product Name: DressLite Ace
Gender: Men's
Color: Black
Price: $73.50MSRP: $105.0030% OFF
Rating

Nunn Bush - Stark Plain Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up. Color Black. On sale for $69.95. MSRP $100.00. 30% off.

Black Nunn Bush Stark Plain Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up

Black Nunn Bush Stark Plain Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up

+2

Brand Name: Nunn Bush
Product Name: Stark Plain Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up
Gender: Men's
Color: Black
Price: $69.95MSRP: $100.0030% OFF
Rating

Deer Stags - Drive Slip-On Loafer. Color Black. On sale for $49.97. MSRP $85.00. 41% off. 3.7 out of 5 stars

Black Deer Stags Drive Slip-On Loafer

Black Deer Stags Drive Slip-On Loafer

Brand Name: Deer Stags
Product Name: Drive Slip-On Loafer
Gender: Men's
Color: Black
Price: $49.97MSRP: $85.0041% OFF
Rating: 4Rated 4 stars out of 5(66)

Marc Joseph New York - Somerville. Color Brown Napa. On sale for $79.95. MSRP $185.00. 57% off. 4.0 out of 5 stars

Brown Marc Joseph New York Somerville

Brown Marc Joseph New York Somerville

+3

Brand Name: Marc Joseph New York
Product Name: Somerville
Gender: Men's
Color: Brown Napa
Price: $79.95MSRP: $185.0057% OFF
Rating: 4Rated 4 stars out of 5(5)

Dockers - Lawton. Color Black Polished. On sale for $59.95. MSRP $90.00. 33% off. 3.6 out of 5 stars

Black Dockers Lawton

Black Dockers Lawton

Brand Name: Dockers
Product Name: Lawton
Gender: Men's
Color: Black Polished
Price: $59.95MSRP: $90.0033% OFF
Rating: 4Rated 4 stars out of 5(25)

Calvin Klein - Olaf. Color Black 1. Low Stock. On sale for $89.10. MSRP $99.00. 10% off. 3.5 out of 5 stars

Low Stock

Black Calvin Klein Olaf

Black Calvin Klein Olaf

Brand Name: Calvin Klein
Product Name: Olaf
Gender: Men's
Color: Black 1
Price: $89.10MSRP: $99.0010% OFF
Rating: 4Rated 4 stars out of 5(6)

Clarks - DressLite Step. Color Black. On sale for $84.00. MSRP $105.00. 20% off.

Black Clarks DressLite Step

Black Clarks DressLite Step

+2

Brand Name: Clarks
Product Name: DressLite Step
Gender: Men's
Color: Black
Price: $84.00MSRP: $105.0020% OFF
Rating

Deer Stags - Elate. Color Black. On sale for $70.00. MSRP $80.00. 13% off.

Black Deer Stags Elate

Black Deer Stags Elate

+2

Brand Name: Deer Stags
Product Name: Elate
Gender: Men's
Color: Black
Price: $70.00MSRP: $80.0013% OFF
Rating

Calvin Klein - Bernard. Color Black/Black/Patent PU. On sale for $99.99. MSRP $119.00. 16% off. 3.0 out of 5 stars

Black Calvin Klein Bernard

Black Calvin Klein Bernard

Brand Name: Calvin Klein
Product Name: Bernard
Gender: Men's
Color: Black/Black/Patent PU
Price: $99.99MSRP: $119.0016% OFF
Rating: 3Rated 3 stars out of 5(4)

Florsheim - Postino Plain Toe Oxford. Color Cognac Smooth/Perf. On sale for $99.95. MSRP $145.00. 31% off. 4.4 out of 5 stars

Brown Florsheim Postino Plain Toe Oxford

Brown Florsheim Postino Plain Toe Oxford

Brand Name: Florsheim
Product Name: Postino Plain Toe Oxford
Gender: Men's
Color: Cognac Smooth/Perf
Price: $99.95MSRP: $145.0031% OFF
Rating: 4Rated 4 stars out of 5(182)

Stacy Adams - Calandro City Sandal. Color White. On sale for $83.73. MSRP $100.00. 16% off. 4.5 out of 5 stars

White Stacy Adams Calandro City Sandal

White Stacy Adams Calandro City Sandal

+3

Brand Name: Stacy Adams
Product Name: Calandro City Sandal
Gender: Men's
Color: White
Price: $83.73MSRP: $100.0016% OFF
Rating: 5Rated 5 stars out of 5(2)

Calvin Klein - Brodie. Color Black/Patent Pu. On sale for $69.97. MSRP $119.00. 41% off. 5.0 out of 5 stars

Black Calvin Klein Brodie

Black Calvin Klein Brodie

Brand Name: Calvin Klein
Product Name: Brodie
Gender: Men's
Color: Black/Patent Pu
Price: $69.97MSRP: $119.0041% OFF
Rating: 5Rated 5 stars out of 5(4)

TOMS - Alpargata Forward Espadrille. Color Black/Black Recycled Cotton Canvas. On sale for $55.00. MSRP $60.00. 8% off. 4.2 out of 5 stars

Black TOMS Alpargata Forward Espadrille

Black TOMS Alpargata Forward Espadrille

Brand Name: TOMS
Product Name: Alpargata Forward Espadrille
Gender: Men's
Color: Black/Black Recycled Cotton Canvas
Price: $55.00MSRP: $60.008% OFF
Rating: 4Rated 4 stars out of 5(11)

Stacy Adams - Pelton Moc Toe Slip-On. Color Tan. On sale for $77.52. MSRP $105.00. 26% off. 4.8 out of 5 stars

Tan Stacy Adams Pelton Moc Toe Slip-On

Tan Stacy Adams Pelton Moc Toe Slip-On

+2

Brand Name: Stacy Adams
Product Name: Pelton Moc Toe Slip-On
Gender: Men's
Color: Tan
Price: $77.52MSRP: $105.0026% OFF
Rating: 5Rated 5 stars out of 5(17)

Stacy Adams - Tristano Bike Toe Lace-Up. Color White. Low Stock. On sale for $95.96. MSRP $115.00. 17% off.

Low Stock

White Stacy Adams Tristano Bike Toe Lace-Up

White Stacy Adams Tristano Bike Toe Lace-Up

+7

Brand Name: Stacy Adams
Product Name: Tristano Bike Toe Lace-Up
Gender: Men's
Color: White
Price: $95.96MSRP: $115.0017% OFF
Rating

Tommy Hilfiger - Senner. Color Black. On sale for $79.99. MSRP $109.00. 27% off. 3.2 out of 5 stars

Black Tommy Hilfiger Senner

Black Tommy Hilfiger Senner

Brand Name: Tommy Hilfiger
Product Name: Senner
Gender: Men's
Color: Black
Price: $79.99MSRP: $109.0027% OFF
Rating: 3Rated 3 stars out of 5(4)

Tommy Hilfiger - Simol. Color Black. On sale for $54.97. MSRP $109.00. 50% off. 3.0 out of 5 stars

Black Tommy Hilfiger Simol

Black Tommy Hilfiger Simol

+2

Brand Name: Tommy Hilfiger
Product Name: Simol
Gender: Men's
Color: Black
Price: $54.97MSRP: $109.0050% OFF
Rating: 3Rated 3 stars out of 5(2)

Tommy Hilfiger - Sesame. Color Black. On sale for $89.99. MSRP $119.00. 24% off. 5.0 out of 5 stars

Black Tommy Hilfiger Sesame

Black Tommy Hilfiger Sesame

+2

Brand Name: Tommy Hilfiger
Product Name: Sesame
Gender: Men's
Color: Black
Price: $89.99MSRP: $119.0024% OFF
Rating: 5Rated 5 stars out of 5(2)

Dockers - Stafford. Color Mahogany. On sale for $49.98. MSRP $90.00. 44% off. 4.2 out of 5 stars

Mahogany Dockers Stafford

Mahogany Dockers Stafford

+2

Brand Name: Dockers
Product Name: Stafford
Gender: Men's
Color: Mahogany
Price: $49.98MSRP: $90.0044% OFF
Rating: 4Rated 4 stars out of 5(8)

Dockers - Irving. Color Black Polished. On sale for $59.99. MSRP $80.00. 25% off. 3.2 out of 5 stars

Black Dockers Irving

Black Dockers Irving

Brand Name: Dockers
Product Name: Irving
Gender: Men's
Color: Black Polished
Price: $59.99MSRP: $80.0025% OFF
Rating: 3Rated 3 stars out of 5(24)

Calvin Klein - Jameson. Color Black. On sale for $79.99. MSRP $130.00. 38% off. 5.0 out of 5 stars

Black Calvin Klein Jameson

Black Calvin Klein Jameson

Brand Name: Calvin Klein
Product Name: Jameson
Gender: Men's
Color: Black
Price: $79.99MSRP: $130.0038% OFF
Rating: 5Rated 5 stars out of 5(1)

Dockers - Stiles. Color Mahogany. On sale for $59.99. MSRP $90.00. 33% off. 2.5 out of 5 stars

Mahogany Dockers Stiles

Mahogany Dockers Stiles

+2

Brand Name: Dockers
Product Name: Stiles
Gender: Men's
Color: Mahogany
Price: $59.99MSRP: $90.0033% OFF
Rating: 3Rated 3 stars out of 5(4)

Tommy Hilfiger - Sawlin. Color Black. On sale for $69.95. MSRP $109.00. 36% off.

Black Tommy Hilfiger Sawlin

Black Tommy Hilfiger Sawlin

Brand Name: Tommy Hilfiger
Product Name: Sawlin
Gender: Men's
Color: Black
Price: $69.95MSRP: $109.0036% OFF
Rating

Tommy Hilfiger - Speer. Color Black. On sale for $79.99. MSRP $109.00. 27% off.

Black Tommy Hilfiger Speer

Black Tommy Hilfiger Speer

Brand Name: Tommy Hilfiger
Product Name: Speer
Gender: Men's
Color: Black
Price: $79.99MSRP: $109.0027% OFF
Rating

Stacy Adams - Rellaire Moc Toe Bit Slip-On. Color Black. On sale for $90.30. MSRP $120.00. 25% off.

Black Stacy Adams Rellaire Moc Toe Bit Slip-On

Black Stacy Adams Rellaire Moc Toe Bit Slip-On

Brand Name: Stacy Adams
Product Name: Rellaire Moc Toe Bit Slip-On
Gender: Men's
Color: Black
Price: $90.30MSRP: $120.0025% OFF
Rating

Roper - James. Color Tan. Low Stock. On sale for $99.44. MSRP $152.99. 35% off.

Low Stock

Tan Roper James

Tan Roper James

Brand Name: Roper
Product Name: James
Gender: Men's
Color: Tan
Price: $99.44MSRP: $152.9935% OFF
Rating

Tommy Hilfiger - Atino. Color Cognac. On sale for $59.95. MSRP $89.00. 33% off. 1.0 out of 5 stars

Tan Tommy Hilfiger Atino

Tan Tommy Hilfiger Atino

+2

Brand Name: Tommy Hilfiger
Product Name: Atino
Gender: Men's
Color: Cognac
Price: $59.95MSRP: $89.0033% OFF
Rating: 1Rated 1 star out of 5(1)

Dockers - Belson. Color Black. Low Stock. On sale for $59.99. MSRP $90.00. 33% off. 5.0 out of 5 stars

Low Stock

Black Dockers Belson

Black Dockers Belson

Brand Name: Dockers
Product Name: Belson
Gender: Men's
Color: Black
Price: $59.99MSRP: $90.0033% OFF
Rating: 5Rated 5 stars out of 5(1)

Stacy Adams - Calderon City Sandal. Color White. On sale for $76.35. MSRP $85.00. 10% off. 4.1 out of 5 stars

White Stacy Adams Calderon City Sandal

White Stacy Adams Calderon City Sandal

Brand Name: Stacy Adams
Product Name: Calderon City Sandal
Gender: Men's
Color: White
Price: $76.35MSRP: $85.0010% OFF
Rating: 4Rated 4 stars out of 5(10)

Marc Joseph New York - Willmington. Color Black Grainy. On sale for $79.95. MSRP $185.00. 57% off. 3.9 out of 5 stars

Black Marc Joseph New York Willmington

Black Marc Joseph New York Willmington

+6

Brand Name: Marc Joseph New York
Product Name: Willmington
Gender: Men's
Color: Black Grainy
Price: $79.95MSRP: $185.0057% OFF
Rating: 4Rated 4 stars out of 5(19)

Eastland 1955 Edition - WHITMAN. Color Brown. Low Stock. On sale for $99.99. MSRP $120.00. 17% off.

Low Stock

Brown Eastland 1955 Edition WHITMAN

Brown Eastland 1955 Edition WHITMAN

+2

Brand Name: Eastland 1955 Edition
Product Name: WHITMAN
Gender: Men's
Color: Brown
Price: $99.99MSRP: $120.0017% OFF
Rating

Marc Joseph New York - Park Avenue. Color Taupe Italo Grainy. On sale for $99.95. MSRP $195.00. 49% off. 2.3 out of 5 stars

Black Marc Joseph New York Park Avenue

Black Marc Joseph New York Park Avenue

+5

Brand Name: Marc Joseph New York
Product Name: Park Avenue
Gender: Men's
Color: Taupe Italo Grainy
Price: $99.95MSRP: $195.0049% OFF
Rating: 2Rated 2 stars out of 5(3)

Tommy Hilfiger - Amile. Color Black. On sale for $69.99. MSRP $89.00. 21% off. 4.6 out of 5 stars

Black Tommy Hilfiger Amile

Black Tommy Hilfiger Amile

+4

Brand Name: Tommy Hilfiger
Product Name: Amile
Gender: Men's
Color: Black
Price: $69.99MSRP: $89.0021% OFF
Rating: 5Rated 5 stars out of 5(5)

Marc Joseph New York - River Road. Color Cognac Grainy. On sale for $69.95. MSRP $185.00. 62% off. 5.0 out of 5 stars

Brown Marc Joseph New York River Road

Brown Marc Joseph New York River Road

+3

Brand Name: Marc Joseph New York
Product Name: River Road
Gender: Men's
Color: Cognac Grainy
Price: $69.95MSRP: $185.0062% OFF
Rating: 5Rated 5 stars out of 5(1)

Stacy Adams - Kallum Cap Toe Oxford. Color Cognac. On sale for $94.99. MSRP $130.00. 27% off. 4.7 out of 5 stars

Tan Stacy Adams Kallum Cap Toe Oxford

Tan Stacy Adams Kallum Cap Toe Oxford

+2

Brand Name: Stacy Adams
Product Name: Kallum Cap Toe Oxford
Gender: Men's
Color: Cognac
Price: $94.99MSRP: $130.0027% OFF
Rating: 5Rated 5 stars out of 5(38)

Marc Joseph New York - Nebraska. Color Havana Nubuck Grainy. On sale for $79.95. MSRP $185.00. 57% off. 3.8 out of 5 stars

Brown Marc Joseph New York Nebraska

Brown Marc Joseph New York Nebraska

+7

Brand Name: Marc Joseph New York
Product Name: Nebraska
Gender: Men's
Color: Havana Nubuck Grainy
Price: $79.95MSRP: $185.0057% OFF
Rating: 4Rated 4 stars out of 5(13)

Johnston & Murphy - Gibbons Bit. Color Tan Hand/Stained Full Grain. On sale for $32.25. MSRP $129.00. 75% off.

Brown Johnston & Murphy Gibbons Bit

Brown Johnston & Murphy Gibbons Bit

+2

Brand Name: Johnston & Murphy
Product Name: Gibbons Bit
Gender: Men's
Color: Tan Hand/Stained Full Grain
Price: $32.25MSRP: $129.0075% OFF
Rating

Clarks - Tilden Cap. Color Dark Tan Leather. On sale for $72.00. MSRP $105.00. 31% off. 4.2 out of 5 stars

Brown Clarks Tilden Cap

Brown Clarks Tilden Cap

+2

Brand Name: Clarks
Product Name: Tilden Cap
Gender: Men's
Color: Dark Tan Leather
Price: $72.00MSRP: $105.0031% OFF
Rating: 4Rated 4 stars out of 5(111)

Rockport - Style Leader 2 Plain Toe. Color Black. On sale for $99.95. MSRP $129.95. 23% off. 4.4 out of 5 stars

Black Rockport Style Leader 2 Plain Toe

Black Rockport Style Leader 2 Plain Toe

+3

Brand Name: Rockport
Product Name: Style Leader 2 Plain Toe
Gender: Men's
Color: Black
Price: $99.95MSRP: $129.9523% OFF
Rating: 4Rated 4 stars out of 5(31)

Florsheim - Sorrento Wing Tip Oxford. Color Black Smooth. On sale for $84.92. MSRP $145.00. 41% off. 4.2 out of 5 stars

Black Florsheim Sorrento Wing Tip Oxford

Black Florsheim Sorrento Wing Tip Oxford

Brand Name: Florsheim
Product Name: Sorrento Wing Tip Oxford
Gender: Men's
Color: Black Smooth
Price: $84.92MSRP: $145.0041% OFF
Rating: 4Rated 4 stars out of 5(40)

Steve Madden - Pippen. Color Cognac. On sale for $68.75. MSRP $125.00. 45% off.

Tan Steve Madden Pippen

Tan Steve Madden Pippen

Brand Name: Steve Madden
Product Name: Pippen
Gender: Men's
Color: Cognac
Price: $68.75MSRP: $125.0045% OFF
Rating

Tommy Hilfiger - Sheldon. Color Black. On sale for $79.99. MSRP $109.00. 27% off. 5.0 out of 5 stars

Black Tommy Hilfiger Sheldon

Black Tommy Hilfiger Sheldon

+2

Brand Name: Tommy Hilfiger
Product Name: Sheldon
Gender: Men's
Color: Black
Price: $79.99MSRP: $109.0027% OFF
Rating: 5Rated 5 stars out of 5(2)

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.)