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

Medium Size Stacked Heel Office & Career Comfort Shoes

43 items found

Sort By

Your Selections

Search Results

Florsheim - Midtown Plain Toe Oxford. Color Black Smooth. On sale for $89.95. MSRP $125.00. 28% off. 4.5 out of 5 stars

Black Florsheim Midtown Plain Toe Oxford

Black Florsheim Midtown Plain Toe Oxford

+2

Brand Name: Florsheim
Product Name: Midtown Plain Toe Oxford
Gender: Men's
Color: Black Smooth
Price: $89.95MSRP: $125.0028% OFF
Rating: 4Rated 4 stars out of 5(343)

Clarks - Whiddon Cap. Color Black Leather. On sale for $76.00. MSRP $95.00. 20% off. 3.8 out of 5 stars

Black Clarks Whiddon Cap

Black Clarks Whiddon Cap

+3

Brand Name: Clarks
Product Name: Whiddon Cap
Gender: Men's
Color: Black Leather
Price: $76.00MSRP: $95.0020% OFF
Rating: 4Rated 4 stars out of 5(85)

Rockport - Style Leader 2 Apron Toe. Color Black Waxed Calf. On sale for $74.99. MSRP $129.95. 42% off. 4.4 out of 5 stars

Black Rockport Style Leader 2 Apron Toe

Black Rockport Style Leader 2 Apron Toe

+2

Brand Name: Rockport
Product Name: Style Leader 2 Apron Toe
Gender: Men's
Color: Black Waxed Calf
Price: $74.99MSRP: $129.9542% OFF
Rating: 4Rated 4 stars out of 5(176)

Cole Haan - Lenox Hill Cap Ox. Color British Tan. $230.00. 4.0 out of 5 stars

Tan Cole Haan Lenox Hill Cap Ox

Tan Cole Haan Lenox Hill Cap Ox

+2

Brand Name: Cole Haan
Product Name: Lenox Hill Cap Ox
Gender: Men's
Color: British Tan
Price: $230.00
Rating: 4Rated 4 stars out of 5(218)

Polo Ralph Lauren - Alston Penny. Color Tan. $178.00. 3.0 out of 5 stars

Tan Polo Ralph Lauren Alston Penny

Tan Polo Ralph Lauren Alston Penny

+3

Brand Name: Polo Ralph Lauren
Product Name: Alston Penny
Gender: Men's
Color: Tan
Price: $178.00
Rating: 3Rated 3 stars out of 5(1)

Florsheim - Rucci Cap Toe Oxford. Color Cognac Smooth. $130.00. 4.6 out of 5 stars

Neutral Florsheim Rucci Cap Toe Oxford

Neutral Florsheim Rucci Cap Toe Oxford

+2

Brand Name: Florsheim
Product Name: Rucci Cap Toe Oxford
Gender: Men's
Color: Cognac Smooth
Price: $130.00
Rating: 5Rated 5 stars out of 5(76)

Stacy Adams - Kallum Cap Toe Oxford. Color Black. On sale for $79.99. MSRP $120.00. 33% off. 4.7 out of 5 stars

Black Stacy Adams Kallum Cap Toe Oxford

Black Stacy Adams Kallum Cap Toe Oxford

+2

Brand Name: Stacy Adams
Product Name: Kallum Cap Toe Oxford
Gender: Men's
Color: Black
Price: $79.99MSRP: $120.0033% OFF
Rating: 5Rated 5 stars out of 5(37)

Nunn Bush - Norcross Cap Toe Dress Casual Oxford. Color Black. On sale for $79.95. MSRP $100.00. 20% off. 4.3 out of 5 stars

Black Nunn Bush Norcross Cap Toe Dress Casual Oxford

Black Nunn Bush Norcross Cap Toe Dress Casual Oxford

+2

Brand Name: Nunn Bush
Product Name: Norcross Cap Toe Dress Casual Oxford
Gender: Men's
Color: Black
Price: $79.95MSRP: $100.0020% OFF
Rating: 4Rated 4 stars out of 5(90)

Johnston & Murphy - Waterproof XC4® Branning Cap Dress Cap Toe Oxford. Color Black Waterproof Calfskin. $174.95. 4.4 out of 5 stars

Black Johnston & Murphy Waterproof XC4® Branning Cap Dress Cap Toe Oxford

Black Johnston & Murphy Waterproof XC4® Branning Cap Dress Cap Toe Oxford

+2

Brand Name: Johnston & Murphy
Product Name: Waterproof XC4® Branning Cap Dress Cap Toe Oxford
Gender: Men's
Color: Black Waterproof Calfskin
Price: $174.95
Rating: 4Rated 4 stars out of 5(145)

Clarks - Tilden Cap. Color Black. On sale for $57.60. MSRP $95.00. 39% off. 4.2 out of 5 stars

Black Clarks Tilden Cap

Black Clarks Tilden Cap

+2

Brand Name: Clarks
Product Name: Tilden Cap
Gender: Men's
Color: Black
Price: $57.60MSRP: $95.0039% OFF
Rating: 4Rated 4 stars out of 5(111)

Nunn Bush - Stark Plain Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up. Color Black. On sale for $69.95. MSRP $94.95. 26% 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: $94.9526% OFF
Rating

Stacy Adams - Gala Cap Toe Oxford. Color Black Patent. On sale for $58.14. MSRP $74.95. 22% off. 4.7 out of 5 stars

Black Stacy Adams Gala Cap Toe Oxford

Black Stacy Adams Gala Cap Toe Oxford

+3

Brand Name: Stacy Adams
Product Name: Gala Cap Toe Oxford
Gender: Men's
Color: Black Patent
Price: $58.14MSRP: $74.9522% OFF
Rating: 5Rated 5 stars out of 5(125)

Dockers - Manvel Moc Toe Oxford. Color Black Polished Full Grain. On sale for $48.08. MSRP $80.00. 40% off. 4.2 out of 5 stars

Black Dockers Manvel Moc Toe Oxford

Black Dockers Manvel Moc Toe Oxford

Brand Name: Dockers
Product Name: Manvel Moc Toe Oxford
Gender: Men's
Color: Black Polished Full Grain
Price: $48.08MSRP: $80.0040% OFF
Rating: 4Rated 4 stars out of 5(67)

Florsheim - Sorrento Cap Toe Oxford. Color Black Smooth. On sale for $89.97. MSRP $130.00. 31% off. 4.7 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: $89.97MSRP: $130.0031% OFF
Rating: 5Rated 5 stars out of 5(106)

Florsheim - Rucci Wing Tip Oxford. Color Black Smooth. On sale for $108.00. MSRP $130.00. 17% off. 4.6 out of 5 stars

Black Florsheim Rucci Wing Tip Oxford

Black Florsheim Rucci Wing Tip Oxford

+3

Brand Name: Florsheim
Product Name: Rucci Wing Tip Oxford
Gender: Men's
Color: Black Smooth
Price: $108.00MSRP: $130.0017% OFF
Rating: 5Rated 5 stars out of 5(81)

Rockport - Charles Road Cap Toe Oxford. Color Black Leather. On sale for $66.17. MSRP $119.95. 45% off. 5.0 out of 5 stars

Black Rockport Charles Road Cap Toe Oxford

Black Rockport Charles Road Cap Toe Oxford

Brand Name: Rockport
Product Name: Charles Road Cap Toe Oxford
Gender: Men's
Color: Black Leather
Price: $66.17MSRP: $119.9545% OFF
Rating: 5Rated 5 stars out of 5(1)

Dockers - Edson Moc Toe Loafer. Color Black Polished Full Grain. On sale for $49.95. MSRP $80.00. 38% off. 4.0 out of 5 stars

Black Dockers Edson Moc Toe Loafer

Black Dockers Edson Moc Toe Loafer

Brand Name: Dockers
Product Name: Edson Moc Toe Loafer
Gender: Men's
Color: Black Polished Full Grain
Price: $49.95MSRP: $80.0038% OFF
Rating: 4Rated 4 stars out of 5(90)

Florsheim - Sorrento Moc Toe Penny Loafer. Color Cognac Smooth. $129.95. 4.2 out of 5 stars

Neutral Florsheim Sorrento Moc Toe Penny Loafer

Neutral Florsheim Sorrento Moc Toe Penny Loafer

+2

Brand Name: Florsheim
Product Name: Sorrento Moc Toe Penny Loafer
Gender: Men's
Color: Cognac Smooth
Price: $129.95
Rating: 4Rated 4 stars out of 5(44)

Johnston & Murphy - Bradford Dress Cap Toe Oxford. Color Black Brush-Off. $129.85. 3.9 out of 5 stars

Black Johnston & Murphy Bradford Dress Cap Toe Oxford

Black Johnston & Murphy Bradford Dress Cap Toe Oxford

Brand Name: Johnston & Murphy
Product Name: Bradford Dress Cap Toe Oxford
Gender: Men's
Color: Black Brush-Off
Price: $129.85
Rating: 4Rated 4 stars out of 5(37)

Clarks - Whiddon Pace. Color Dark Tan Leather. On sale for $59.97. MSRP $95.00. 37% off. 3.8 out of 5 stars

Brown Clarks Whiddon Pace

Brown Clarks Whiddon Pace

+2

Brand Name: Clarks
Product Name: Whiddon Pace
Gender: Men's
Color: Dark Tan Leather
Price: $59.97MSRP: $95.0037% OFF
Rating: 4Rated 4 stars out of 5(49)

Stacy Adams - Savian Velour Slip-On. Color Black. On sale for $64.00. MSRP $80.00. 20% off. 5.0 out of 5 stars

Black Stacy Adams Savian Velour Slip-On

Black Stacy Adams Savian Velour Slip-On

Brand Name: Stacy Adams
Product Name: Savian Velour Slip-On
Gender: Men's
Color: Black
Price: $64.00MSRP: $80.0020% OFF
Rating: 5Rated 5 stars out of 5(11)

Marc Joseph New York - Harman ST. Color Black Grainy. Low Stock. On sale for $155.75. MSRP $175.00. 11% off.

Low Stock

Black Marc Joseph New York Harman ST

Black Marc Joseph New York Harman ST

Brand Name: Marc Joseph New York
Product Name: Harman ST
Gender: Men's
Color: Black Grainy
Price: $155.75MSRP: $175.0011% OFF
Rating

Florsheim - Lodge Moc Toe Oxford. Color Brown Crazy Horse. On sale for $99.99. MSRP $115.00. 13% off. 4.6 out of 5 stars

Brown Florsheim Lodge Moc Toe Oxford

Brown Florsheim Lodge Moc Toe Oxford

Brand Name: Florsheim
Product Name: Lodge Moc Toe Oxford
Gender: Men's
Color: Brown Crazy Horse
Price: $99.99MSRP: $115.0013% OFF
Rating: 5Rated 5 stars out of 5(34)

Calvin Klein - Brinta. Color Black. On sale for $83.30. MSRP $119.00. 30% off.

Black Calvin Klein Brinta

Black Calvin Klein Brinta

Brand Name: Calvin Klein
Product Name: Brinta
Gender: Men's
Color: Black
Price: $83.30MSRP: $119.0030% OFF
Rating

Florsheim - Highland Plain Toe Oxford. Color Cognac Smooth/White Sole. $119.95. 4.4 out of 5 stars

Brown Florsheim Highland Plain Toe Oxford

Brown Florsheim Highland Plain Toe Oxford

Brand Name: Florsheim
Product Name: Highland Plain Toe Oxford
Gender: Men's
Color: Cognac Smooth/White Sole
Price: $119.95
Rating: 4Rated 4 stars out of 5(117)

Nunn Bush - Centro Flex Formal Plain Toe Oxford. Color Black Patent. On sale for $49.95. MSRP $80.00. 38% off. 4.4 out of 5 stars

Black Nunn Bush Centro Flex Formal Plain Toe Oxford

Black Nunn Bush Centro Flex Formal Plain Toe Oxford

Brand Name: Nunn Bush
Product Name: Centro Flex Formal Plain Toe Oxford
Gender: Men's
Color: Black Patent
Price: $49.95MSRP: $80.0038% OFF
Rating: 4Rated 4 stars out of 5(7)

Florsheim - Postino Cap Toe. Color Cognac Smooth. On sale for $69.17. MSRP $130.00. 47% off. 4.6 out of 5 stars

Neutral Florsheim Postino Cap Toe

Neutral Florsheim Postino Cap Toe

Brand Name: Florsheim
Product Name: Postino Cap Toe
Gender: Men's
Color: Cognac Smooth
Price: $69.17MSRP: $130.0047% OFF
Rating: 5Rated 5 stars out of 5(84)

Johnston & Murphy Collection - Cormac Cap Toe. Color Black Italian Calfskin. $294.95. 4.7 out of 5 stars

Black Johnston & Murphy Collection Cormac Cap Toe

Black Johnston & Murphy Collection Cormac Cap Toe

+3

Brand Name: Johnston & Murphy Collection
Product Name: Cormac Cap Toe
Gender: Men's
Color: Black Italian Calfskin
Price: $294.95
Rating: 5Rated 5 stars out of 5(55)

Dockers - Fairway. Color Black. On sale for $49.99. MSRP $90.00. 44% off. 4.0 out of 5 stars

Black Dockers Fairway

Black Dockers Fairway

Brand Name: Dockers
Product Name: Fairway
Gender: Men's
Color: Black
Price: $49.99MSRP: $90.0044% OFF
Rating: 4Rated 4 stars out of 5(1)

Allen Edmonds - Park Avenue Oxford. Color Black Custom Calf. $425.00. 4.4 out of 5 stars

Black Allen Edmonds Park Avenue Oxford

Black Allen Edmonds Park Avenue Oxford

+2

Brand Name: Allen Edmonds
Product Name: Park Avenue Oxford
Gender: Men's
Color: Black Custom Calf
Price: $425.00
Rating: 4Rated 4 stars out of 5(202)

Clarks - Whiddon Apron. Color Black Tumbled. On sale for $85.45. MSRP $95.00. 10% off.

Black Clarks Whiddon Apron

Black Clarks Whiddon Apron

Brand Name: Clarks
Product Name: Whiddon Apron
Gender: Men's
Color: Black Tumbled
Price: $85.45MSRP: $95.0010% OFF
Rating

Allen Edmonds - Carlyle. Color Black Custom Calf. $425.00. 4.4 out of 5 stars

Black Allen Edmonds Carlyle

Black Allen Edmonds Carlyle

+4

Brand Name: Allen Edmonds
Product Name: Carlyle
Gender: Men's
Color: Black Custom Calf
Price: $425.00
Rating: 4Rated 4 stars out of 5(227)

Allen Edmonds - Strand. Color Walnut Calf. $425.00. 4.6 out of 5 stars

Brown Allen Edmonds Strand

Brown Allen Edmonds Strand

+3

Brand Name: Allen Edmonds
Product Name: Strand
Gender: Men's
Color: Walnut Calf
Price: $425.00
Rating: 5Rated 5 stars out of 5(627)

Johnston & Murphy Collection - Flynch Plain Toe. Color Tan Italian Calfskin. $297.95. 4.0 out of 5 stars

Tan Johnston & Murphy Collection Flynch Plain Toe

Tan Johnston & Murphy Collection Flynch Plain Toe

+1

Brand Name: Johnston & Murphy Collection
Product Name: Flynch Plain Toe
Gender: Men's
Color: Tan Italian Calfskin
Price: $297.95
Rating: 4Rated 4 stars out of 5(2)

Stacy Adams - Reynolds Cap Toe Lace-Up. Color Burgundy Multi. On sale for $96.00. MSRP $120.00. 20% off. 3.0 out of 5 stars

Burgundy Stacy Adams Reynolds Cap Toe Lace-Up

Burgundy Stacy Adams Reynolds Cap Toe Lace-Up

+1

Brand Name: Stacy Adams
Product Name: Reynolds Cap Toe Lace-Up
Gender: Men's
Color: Burgundy Multi
Price: $96.00MSRP: $120.0020% OFF
Rating: 3Rated 3 stars out of 5(2)

Johnston & Murphy Collection - Flynch Cap Toe. Color Tan Italian Calfskin. Low Stock. On sale for $268.20. MSRP $298.00. 10% off. 3.1 out of 5 stars

Low Stock

Tan Johnston & Murphy Collection Flynch Cap Toe

Tan Johnston & Murphy Collection Flynch Cap Toe

+3

Brand Name: Johnston & Murphy Collection
Product Name: Flynch Cap Toe
Gender: Men's
Color: Tan Italian Calfskin
Price: $268.20MSRP: $298.0010% OFF
Rating: 3Rated 3 stars out of 5(10)

Rockport - Charles Road Cap Toe Oxford. Color Dark Brown. On sale for $73.01. MSRP $119.95. 39% off. 3.7 out of 5 stars

Brown Rockport Charles Road Cap Toe Oxford

Brown Rockport Charles Road Cap Toe Oxford

+3

Brand Name: Rockport
Product Name: Charles Road Cap Toe Oxford
Gender: Men's
Color: Dark Brown
Price: $73.01MSRP: $119.9539% OFF
Rating: 4Rated 4 stars out of 5(3)

Magnanni - Malta. Color Cognac. Low Stock. $435.00.

Low Stock

Tan Magnanni Malta

Tan Magnanni Malta

Brand Name: Magnanni
Product Name: Malta
Gender: Men's
Color: Cognac
Price: $435.00
Rating

Florsheim - Santucci Cap Toe Oxford. Color Black. Low Stock. On sale for $79.97. MSRP $110.00. 27% off. 4.5 out of 5 stars

Low Stock

Black Florsheim Santucci Cap Toe Oxford

Black Florsheim Santucci Cap Toe Oxford

Brand Name: Florsheim
Product Name: Santucci Cap Toe Oxford
Gender: Men's
Color: Black
Price: $79.97MSRP: $110.0027% OFF
Rating: 5Rated 5 stars out of 5(30)

Ariat - Midtown Rambler Boots. Color Matte Black. $159.95. 4.5 out of 5 stars

Black Ariat Midtown Rambler Boots

Black Ariat Midtown Rambler Boots

Brand Name: Ariat
Product Name: Midtown Rambler Boots
Gender: Men's
Color: Matte Black
Price: $159.95
Rating: 4Rated 4 stars out of 5(19)

Rockport - Next Gen Cap Toe. Color Black. Low Stock. On sale for $78.25. MSRP $129.95. 40% off.

Low Stock

Black Rockport Next Gen Cap Toe

Black Rockport Next Gen Cap Toe

Brand Name: Rockport
Product Name: Next Gen Cap Toe
Gender: Men's
Color: Black
Price: $78.25MSRP: $129.9540% OFF
Rating

Allen Edmonds - Park Avenue Cap Toes. Color Espresso Leather. $425.00.

Brown Allen Edmonds Park Avenue Cap Toes

Brown Allen Edmonds Park Avenue Cap Toes

Brand Name: Allen Edmonds
Product Name: Park Avenue Cap Toes
Gender: Men's
Color: Espresso Leather
Price: $425.00
Rating

COACH - Cooper Loafer. Color Black. On sale for $187.00. MSRP $275.00. 32% off.

Black COACH Cooper Loafer

Black COACH Cooper Loafer

Brand Name: COACH
Product Name: Cooper Loafer
Gender: Men's
Color: Black
Price: $187.00MSRP: $275.0032% OFF
Rating

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.)