EXTRA 20% OFF*
*Offer ends 12/29/25 at 11:59pm PST. Exclusions apply.
Hurry, hurry: use code SAVE20
Select styles only.
Shop Now

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

Size 9.5 Square Toe Comfort On Sale Products

39 items found

Sort By

Your Selections

Search Results

Florsheim - Sorrento Cap Toe Oxford. Color Black Smooth. On sale for $109.95. MSRP $145.00. 24% off. 4.6 out of 5 stars

Black Florsheim Sorrento Cap Toe Oxford

Black Florsheim Sorrento Cap Toe Oxford

+2

Brand Name: Florsheim
Product Name: Sorrento Cap Toe Oxford
Gender: Men's
Color: Black Smooth
Price: $109.95MSRP: $14524% OFF
Rating: 5Rated 5 stars out of 5(115)

Kenneth Cole - Theme Bit Detail Driver. Color Black. On sale for $108.75. MSRP $144.95. 25% off.

Black Kenneth Cole Theme Bit Detail Driver

Black Kenneth Cole Theme Bit Detail Driver

+2

Brand Name: Kenneth Cole
Product Name: Theme Bit Detail Driver
Gender: Men's
Color: Black
Price: $108.75MSRP: $144.9525% OFF
Rating

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

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(335)

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: $9033% OFF
Rating: 4Rated 4 stars out of 5(3)

Florsheim - Sorrento Moc Toe Penny Loafers. Color Cognac Smooth. On sale for $109.95. MSRP $145.00. 24% off. 4.3 out of 5 stars

Neutral Florsheim Sorrento Moc Toe Penny Loafers

Neutral Florsheim Sorrento Moc Toe Penny Loafers

+2

Brand Name: Florsheim
Product Name: Sorrento Moc Toe Penny Loafers
Gender: Men's
Color: Cognac Smooth
Price: $109.95MSRP: $14524% OFF
Rating: 4Rated 4 stars out of 5(54)

Dockers - Lawton. Color Black Polished. On sale for $49.99. MSRP $90.00. 44% off. 3.7 out of 5 stars

Black Dockers Lawton

Black Dockers Lawton

Brand Name: Dockers
Product Name: Lawton
Gender: Men's
Color: Black Polished
Price: $49.99MSRP: $9044% OFF
Rating: 4Rated 4 stars out of 5(27)

Rockport - Seaver. Color Brown Leather. On sale for $109.95. MSRP $129.95. 15% off. 2.0 out of 5 stars

Brown Rockport Seaver

Brown Rockport Seaver

+2

Brand Name: Rockport
Product Name: Seaver
Gender: Men's
Color: Brown Leather
Price: $109.95MSRP: $129.9515% OFF
Rating: 2Rated 2 stars out of 5(1)

Florsheim - Jackson Cap Toe Oxford. Color Cognac. On sale for $89.95. MSRP $120.00. 25% off. 4.4 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: $12025% OFF
Rating: 4Rated 4 stars out of 5(60)

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

Black Stacy Adams Kallum Cap Toe Oxford

Black Stacy Adams Kallum Cap Toe Oxford

+3

Brand Name: Stacy Adams
Product Name: Kallum Cap Toe Oxford
Gender: Men's
Color: Black
Price: $94.99MSRP: $13027% OFF
Rating: 5Rated 5 stars out of 5(39)

Clarks - DressLite Step. Color Black. Low Stock. On sale for $80.50. MSRP $105.00. 23% off.

Low Stock

Black Clarks DressLite Step

Black Clarks DressLite Step

+2

Brand Name: Clarks
Product Name: DressLite Step
Gender: Men's
Color: Black
Price: $80.50MSRP: $10523% OFF
Rating

Clarks - Shacre Boots. Color Black Leather. On sale for $82.50. MSRP $120.00. 31% off. 4.2 out of 5 stars

Black Clarks Shacre Boots

Black Clarks Shacre Boots

+4

Brand Name: Clarks
Product Name: Shacre Boots
Gender: Men's
Color: Black Leather
Price: $82.50MSRP: $12031% OFF
Rating: 4Rated 4 stars out of 5(69)

Florsheim - Corbetta Cap Toe Oxford. Color Black Smooth. On sale for $124.95. MSRP $140.00. 11% off. 4.4 out of 5 stars

Black Florsheim Corbetta Cap Toe Oxford

Black Florsheim Corbetta Cap Toe Oxford

+2

Brand Name: Florsheim
Product Name: Corbetta Cap Toe Oxford
Gender: Men's
Color: Black Smooth
Price: $124.95MSRP: $14011% OFF
Rating: 4Rated 4 stars out of 5(196)

Florsheim - Postino Cap Toe Oxford. Color Cognac Smooth/Perf. On sale for $109.99. MSRP $145.00. 24% off. 4.4 out of 5 stars

Brown Florsheim Postino Cap Toe Oxford

Brown Florsheim Postino Cap Toe Oxford

+2

Brand Name: Florsheim
Product Name: Postino Cap Toe Oxford
Gender: Men's
Color: Cognac Smooth/Perf
Price: $109.99MSRP: $14524% OFF
Rating: 4Rated 4 stars out of 5(211)

Dockers - Irving. Color Black Polished. On sale for $49.99. MSRP $90.00. 44% 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: $49.99MSRP: $9044% OFF
Rating: 3Rated 3 stars out of 5(24)

Nunn Bush - Stark Plain Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up. Color Cognac. On sale for $69.95. MSRP $100.00. 30% off. 2.0 out of 5 stars

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

Tan 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: Cognac
Price: $69.95MSRP: $10030% OFF
Rating: 2Rated 2 stars out of 5(1)

Deer Stags - Coney. Color Black. On sale for $49.97. MSRP $80.00. 38% off. 4.0 out of 5 stars

Black Deer Stags Coney

Black Deer Stags Coney

Brand Name: Deer Stags
Product Name: Coney
Gender: Men's
Color: Black
Price: $49.97MSRP: $8038% OFF
Rating: 4Rated 4 stars out of 5(4)

Florsheim - Sorrento Wing Tip Oxford. Color Black Smooth. On sale for $109.95. MSRP $145.00. 24% off. 4.3 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: $109.95MSRP: $14524% OFF
Rating: 4Rated 4 stars out of 5(45)

ALDO - Luigi. Color Black. Low Stock. On sale for $64.00. MSRP $128.00. 50% off.

Low Stock

Black ALDO Luigi

Black ALDO Luigi

+2

Brand Name: ALDO
Product Name: Luigi
Gender: Men's
Color: Black
Price: $64MSRP: $12850% OFF
Rating

Deer Stags - Elate. Color Black. On sale for $56.00. MSRP $80.00. 30% off.

Black Deer Stags Elate

Black Deer Stags Elate

+2

Brand Name: Deer Stags
Product Name: Elate
Gender: Men's
Color: Black
Price: $56MSRP: $8030% OFF
Rating

Deer Stags - Easton. Color Dark Luggage. On sale for $49.99. MSRP $80.00. 38% off. 2.5 out of 5 stars

Brown Deer Stags Easton

Brown Deer Stags Easton

+2

Brand Name: Deer Stags
Product Name: Easton
Gender: Men's
Color: Dark Luggage
Price: $49.99MSRP: $8038% OFF
Rating: 3Rated 3 stars out of 5(2)

Calvin Klein - Brinta. Color Black. On sale for $71.40. MSRP $119.00. 40% off. 4.0 out of 5 stars

Black Calvin Klein Brinta

Black Calvin Klein Brinta

Brand Name: Calvin Klein
Product Name: Brinta
Gender: Men's
Color: Black
Price: $71.40MSRP: $11940% OFF
Rating: 4Rated 4 stars out of 5(1)

To Boot New York - Christophe. Color Grey. Low Stock. On sale for $396.00. MSRP $495.00. 20% off.

Low Stock

Gray To Boot New York Christophe

Gray To Boot New York Christophe

+3

Brand Name: To Boot New York
Product Name: Christophe
Gender: Men's
Color: Grey
Price: $396MSRP: $49520% OFF
Rating

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: $18562% OFF
Rating: 5Rated 5 stars out of 5(1)

Steve Madden - Haynes. Color Black Leat. Low Stock. On sale for $144.50. MSRP $170.00. 15% off. 3.0 out of 5 stars

Low Stock

Black Steve Madden Haynes

Black Steve Madden Haynes

Brand Name: Steve Madden
Product Name: Haynes
Gender: Men's
Color: Black Leat
Price: $144.50MSRP: $17015% OFF
Rating: 3Rated 3 stars out of 5(1)

Steve Madden - Jasper. Color Taupe. Low Stock. On sale for $142.73. MSRP $175.00. 18% off.

Low Stock

Taupe Steve Madden Jasper

Taupe Steve Madden Jasper

Brand Name: Steve Madden
Product Name: Jasper
Gender: Men's
Color: Taupe
Price: $142.73MSRP: $17518% OFF
Rating

Tommy Hilfiger - Speer. Color Black. Low Stock. On sale for $65.40. MSRP $109.00. 40% off.

Low Stock

Black Tommy Hilfiger Speer

Black Tommy Hilfiger Speer

+2

Brand Name: Tommy Hilfiger
Product Name: Speer
Gender: Men's
Color: Black
Price: $65.40MSRP: $10940% OFF
Rating

Stacy Adams - Calandro City Sandal. Color Black. Low Stock. On sale for $82.83. MSRP $100.00. 17% off. 3.8 out of 5 stars

Low Stock

Black Stacy Adams Calandro City Sandal

Black Stacy Adams Calandro City Sandal

+3

Brand Name: Stacy Adams
Product Name: Calandro City Sandal
Gender: Men's
Color: Black
Price: $82.83MSRP: $10017% OFF
Rating: 4Rated 4 stars out of 5(4)

Steve Madden - Paulson. Color Black. On sale for $109.20. MSRP $130.00. 16% off.

Black Steve Madden Paulson

Black Steve Madden Paulson

Brand Name: Steve Madden
Product Name: Paulson
Gender: Men's
Color: Black
Price: $109.20MSRP: $13016% OFF
Rating

Rockport - Style Leader 2 Plain Toe. Color British Tan. On sale for $99.95. MSRP $129.95. 23% off. 4.2 out of 5 stars

Tan Rockport Style Leader 2 Plain Toe

Tan Rockport Style Leader 2 Plain Toe

+3

Brand Name: Rockport
Product Name: Style Leader 2 Plain Toe
Gender: Men's
Color: British Tan
Price: $99.95MSRP: $129.9523% OFF
Rating: 4Rated 4 stars out of 5(34)

Stacy Adams - Tristano Bike Toe Lace-Up. Color Gray Multi. On sale for $96.05. MSRP $115.00. 16% off. 5.0 out of 5 stars

Brown Stacy Adams Tristano Bike Toe Lace-Up

Brown Stacy Adams Tristano Bike Toe Lace-Up

+6

Brand Name: Stacy Adams
Product Name: Tristano Bike Toe Lace-Up
Gender: Men's
Color: Gray Multi
Price: $96.05MSRP: $11516% OFF
Rating: 5Rated 5 stars out of 5(2)

Tommy Hilfiger - Steran. Color Black. On sale for $54.97. MSRP $109.00. 50% off. 5.0 out of 5 stars

Black Tommy Hilfiger Steran

Black Tommy Hilfiger Steran

+2

Brand Name: Tommy Hilfiger
Product Name: Steran
Gender: Men's
Color: Black
Price: $54.97MSRP: $10950% OFF
Rating: 5Rated 5 stars out of 5(1)

Clarks - Tilden Cap. Color Dark Tan Leather. On sale for $67.50. MSRP $105.00. 36% 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: $67.50MSRP: $10536% OFF
Rating: 4Rated 4 stars out of 5(113)

Clarks - DressLite Ace. Color Black. On sale for $80.50. MSRP $105.00. 23% off. 4.0 out of 5 stars

Black Clarks DressLite Ace

Black Clarks DressLite Ace

+2

Brand Name: Clarks
Product Name: DressLite Ace
Gender: Men's
Color: Black
Price: $80.50MSRP: $10523% OFF
Rating: 4Rated 4 stars out of 5(1)

ECCO - Helsinki 2.0 Apron Toe Slip-On. Color Cognac/Cognac. On sale for $161.95. MSRP $179.95. 10% off. 3.9 out of 5 stars

Bronze ECCO Helsinki 2.0 Apron Toe Slip-On

Bronze ECCO Helsinki 2.0 Apron Toe Slip-On

+3

Brand Name: ECCO
Product Name: Helsinki 2.0 Apron Toe Slip-On
Gender: Men's
Color: Cognac/Cognac
Price: $161.95MSRP: $179.9510% OFF
Rating: 4Rated 4 stars out of 5(54)

Rockport - Tayo. Color Dark Brown Embossed Leather. On sale for $64.99. MSRP $129.95. 50% off.

Brown Rockport Tayo

Brown Rockport Tayo

Brand Name: Rockport
Product Name: Tayo
Gender: Men's
Color: Dark Brown Embossed Leather
Price: $64.99MSRP: $129.9550% OFF
Rating

To Boot New York - Alfonse. Color Dark Brown 1. Low Stock. On sale for $247.50. MSRP $450.00. 45% off.

Low Stock

Brown To Boot New York Alfonse

Brown To Boot New York Alfonse

+2

Brand Name: To Boot New York
Product Name: Alfonse
Gender: Men's
Color: Dark Brown 1
Price: $247.50MSRP: $45045% OFF
Rating

Allbirds - Wool Slipper Fluff. Color Natural White (Natural White). On sale for $67.50. MSRP $75.00. 10% off. 5.0 out of 5 stars

White Allbirds Wool Slipper Fluff

White Allbirds Wool Slipper Fluff

+2

Brand Name: Allbirds
Product Name: Wool Slipper Fluff
Gender: Unisex
Color: Natural White (Natural White)
Price: $67.50MSRP: $7510% OFF
Rating: 5Rated 5 stars out of 5(2)

Johnston & Murphy - Gibbons Bit. Color Tan Hand/Stained Full Grain. Low Stock. On sale for $64.50. MSRP $129.00. 50% off. 4.0 out of 5 stars

Low Stock

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: $64.50MSRP: $12950% OFF
Rating: 4Rated 4 stars out of 5(3)

Ariat - Sting Cowboy Boots. Color Honey Tan. Low Stock. On sale for $195.96. MSRP $279.95. 30% off. 4.6 out of 5 stars

Low Stock

Beige Ariat Sting Cowboy Boots

Beige Ariat Sting Cowboy Boots

Brand Name: Ariat
Product Name: Sting Cowboy Boots
Gender: Men's
Color: Honey Tan
Price: $195.96MSRP: $279.9530% OFF
Rating: 5Rated 5 stars out of 5(26)

Join Our Email List

Never miss out on latest drops & sales—plus, new subscribers get 10% off.*

*One code per email address.