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

Medium Size 2-3in Mid Heel Size Leather Casual Shoes

45 items found

Sort By

Your Selections

Search Results

KEEN Utility - Skokie Waterproof Work Boot (Soft Toe). Color Forest Night/Black. $144.95. 5.0 out of 5 stars

Green KEEN Utility Skokie Waterproof Work Boot (Soft Toe)

Green KEEN Utility Skokie Waterproof Work Boot (Soft Toe)

+3

Brand Name: KEEN Utility
Product Name: Skokie Waterproof Work Boot (Soft Toe)
Gender: Men's
Color: Forest Night/Black
Price: $144.95
Rating: 5Rated 5 stars out of 5(1)

Dansko - Professional Clog. Color Black Cabrio Leather. $154.95. 4.0 out of 5 stars

Black Dansko Professional Clog

Black Dansko Professional Clog

+4

Brand Name: Dansko
Product Name: Professional Clog
Gender: Men's
Color: Black Cabrio Leather
Price: $154.95
Rating: 4Rated 4 stars out of 5(108)

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

Low Stock

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: Brown Grainy
Price: $69.95MSRP: $185.0062% OFF
Rating: 5Rated 5 stars out of 5(1)

TravisMathew - The Daily 2.0 Woven. Color White. $119.95. 4.4 out of 5 stars

White TravisMathew The Daily 2.0 Woven

White TravisMathew The Daily 2.0 Woven

+4

Brand Name: TravisMathew
Product Name: The Daily 2.0 Woven
Gender: Men's
Color: White
Price: $119.95
Rating: 4Rated 4 stars out of 5(173)

Johnston & Murphy - Reeve Chelsea Boots. Color Tan Full Grain. $139.90.

Tan Johnston & Murphy Reeve Chelsea Boots

Tan Johnston & Murphy Reeve Chelsea Boots

+2

Brand Name: Johnston & Murphy
Product Name: Reeve Chelsea Boots
Gender: Men's
Color: Tan Full Grain
Price: $139.90
Rating

TravisMathew - The Daily Lite. Color Heather Natural. Low Stock. On sale for $129.47. MSRP $139.95. 7% off. 4.2 out of 5 stars

Low Stock

Gray TravisMathew The Daily Lite

Gray TravisMathew The Daily Lite

+4

Brand Name: TravisMathew
Product Name: The Daily Lite
Gender: Men's
Color: Heather Natural
Price: $129.47MSRP: $139.957% OFF
Rating: 4Rated 4 stars out of 5(175)

Dansko - Karl Clog. Color Black Oiled. $144.95. 4.4 out of 5 stars

Black Dansko Karl Clog

Black Dansko Karl Clog

+1

Brand Name: Dansko
Product Name: Karl Clog
Gender: Men's
Color: Black Oiled
Price: $144.95
Rating: 4Rated 4 stars out of 5(228)

Dansko - Frankie. Color Brown Oiled. $179.95. 4.2 out of 5 stars

Brown Dansko Frankie

Brown Dansko Frankie

+3

Brand Name: Dansko
Product Name: Frankie
Gender: Women's
Color: Brown Oiled
Price: $179.95
Rating: 4Rated 4 stars out of 5(294)

Danner - Trail Junction 3". Color Bracken/Peridot Green. $143.95. 2.6 out of 5 stars

Beige Danner Trail Junction 3"

Beige Danner Trail Junction 3"

+2

Brand Name: Danner
Product Name: Trail Junction 3"
Gender: Men's
Color: Bracken/Peridot Green
Price: $143.95
Rating: 3Rated 3 stars out of 5(8)

KEEN Utility - Skokie Waterproof Work Boot (Carbon Toe). Color Camo/Black. $154.95.

Multi KEEN Utility Skokie Waterproof Work Boot (Carbon Toe)

Multi KEEN Utility Skokie Waterproof Work Boot (Carbon Toe)

+3

Brand Name: KEEN Utility
Product Name: Skokie Waterproof Work Boot (Carbon Toe)
Gender: Men's
Color: Camo/Black
Price: $154.95
Rating

Clarks - DressLite Step. Color Dark Tan. On sale for $66.15. MSRP $105.00. 37% off.

Brown Clarks DressLite Step

Brown Clarks DressLite Step

+2

Brand Name: Clarks
Product Name: DressLite Step
Gender: Men's
Color: Dark Tan
Price: $66.15MSRP: $105.0037% OFF
Rating

Johnston & Murphy - Reeve Zip Boots. Color Black Full Grain. $139.90.

Black Johnston & Murphy Reeve Zip Boots

Black Johnston & Murphy Reeve Zip Boots

Brand Name: Johnston & Murphy
Product Name: Reeve Zip Boots
Gender: Men's
Color: Black Full Grain
Price: $139.90
Rating

Dansko - Lilah. Color Tan Oiled Pull Up. $159.95. 4.0 out of 5 stars

Tan Dansko Lilah

Tan Dansko Lilah

+2

Brand Name: Dansko
Product Name: Lilah
Gender: Women's
Color: Tan Oiled Pull Up
Price: $159.95
Rating: 4Rated 4 stars out of 5(6)

Johnston & Murphy - Barrett Zip Boots. Color Brown Waxed Suede. $198.95. 3.0 out of 5 stars

Brown Johnston & Murphy Barrett Zip Boots

Brown Johnston & Murphy Barrett Zip Boots

+2

Brand Name: Johnston & Murphy
Product Name: Barrett Zip Boots
Gender: Men's
Color: Brown Waxed Suede
Price: $198.95
Rating: 3Rated 3 stars out of 5(1)

Wolf & Shepherd - Supercrossover. Color Honey. $295.00.

Tan Wolf & Shepherd Supercrossover

Tan Wolf & Shepherd Supercrossover

+2

Brand Name: Wolf & Shepherd
Product Name: Supercrossover
Gender: Men's
Color: Honey
Price: $295.00
Rating

Johnston & Murphy - Xc+ Parker Chukka. Color Black Waterproof Full Grain. $188.95.

Black Johnston & Murphy Xc+ Parker Chukka

Black Johnston & Murphy Xc+ Parker Chukka

+2

Brand Name: Johnston & Murphy
Product Name: Xc+ Parker Chukka
Gender: Men's
Color: Black Waterproof Full Grain
Price: $188.95
Rating

Marc Joseph New York - South Street. Color Cognac Grainy. On sale for $79.95. MSRP $155.00. 48% off. 1.0 out of 5 stars

Brown Marc Joseph New York South Street

Brown Marc Joseph New York South Street

Brand Name: Marc Joseph New York
Product Name: South Street
Gender: Men's
Color: Cognac Grainy
Price: $79.95MSRP: $155.0048% OFF
Rating: 1Rated 1 star out of 5(1)

Vans - FU MTE Ultrarange EXO SE. Color Lavender Fog. On sale for $59.00. MSRP $100.00. 41% off. 2.7 out of 5 stars

Purple Vans FU MTE Ultrarange EXO SE

Purple Vans FU MTE Ultrarange EXO SE

Brand Name: Vans
Product Name: FU MTE Ultrarange EXO SE
Gender: Women's
Color: Lavender Fog
Price: $59.00MSRP: $100.0041% OFF
Rating: 3Rated 3 stars out of 5(12)

Marc Joseph New York - Cooper St. Color Oilve Suede. On sale for $89.95. MSRP $195.00. 54% off. 2.0 out of 5 stars

Olive Marc Joseph New York Cooper St

Olive Marc Joseph New York Cooper St

+6

Brand Name: Marc Joseph New York
Product Name: Cooper St
Gender: Men's
Color: Oilve Suede
Price: $89.95MSRP: $195.0054% OFF
Rating: 2Rated 2 stars out of 5(1)

Dr. Martens - 1B99 Quad. Color Black. On sale for $161.00. MSRP $230.00. 30% off. 1.0 out of 5 stars

Black Dr. Martens 1B99 Quad

Black Dr. Martens 1B99 Quad

Brand Name: Dr. Martens
Product Name: 1B99 Quad
Gender: Unisex
Color: Black
Price: $161.00MSRP: $230.0030% OFF
Rating: 1Rated 1 star out of 5(1)

Dr. Martens - Myles. Color Black Brando. On sale for $106.70. MSRP $120.00. 11% off. 4.3 out of 5 stars

Black Dr. Martens Myles

Black Dr. Martens Myles

+1

Brand Name: Dr. Martens
Product Name: Myles
Gender: Unisex
Color: Black Brando
Price: $106.70MSRP: $120.0011% OFF
Rating: 4Rated 4 stars out of 5(31)

Sanita - Original-Karl PU Open. Color Black. Low Stock. $115.00. 3.9 out of 5 stars

Low Stock

Black Sanita Original-Karl PU Open

Black Sanita Original-Karl PU Open

Brand Name: Sanita
Product Name: Original-Karl PU Open
Gender: Men's
Color: Black
Price: $115.00
Rating: 4Rated 4 stars out of 5(12)

Dr. Martens - Jadon Smooth Leather Platform Boots. Color Black Polished Smooth. $199.95. 4.5 out of 5 stars

Black Dr. Martens Jadon Smooth Leather Platform Boots

Black Dr. Martens Jadon Smooth Leather Platform Boots

Brand Name: Dr. Martens
Product Name: Jadon Smooth Leather Platform Boots
Gender: Men's
Color: Black Polished Smooth
Price: $199.95
Rating: 4Rated 4 stars out of 5(70)

Laredo - Breakout. Color Rust Distressed. $154.95. 3.7 out of 5 stars

Orange Laredo Breakout

Orange Laredo Breakout

Brand Name: Laredo
Product Name: Breakout
Gender: Men's
Color: Rust Distressed
Price: $154.95
Rating: 4Rated 4 stars out of 5(22)

Dr. Martens - Adrian Quad Leather Platform Loafers. Color Black Smooth. $179.95. 2.7 out of 5 stars

Black Dr. Martens Adrian Quad Leather Platform Loafers

Black Dr. Martens Adrian Quad Leather Platform Loafers

Brand Name: Dr. Martens
Product Name: Adrian Quad Leather Platform Loafers
Gender: Unisex
Color: Black Smooth
Price: $179.95
Rating: 3Rated 3 stars out of 5(7)

Laredo - Brentwood. Color Black. $154.95. 4.6 out of 5 stars

Black Laredo Brentwood

Black Laredo Brentwood

Brand Name: Laredo
Product Name: Brentwood
Gender: Men's
Color: Black
Price: $154.95
Rating: 5Rated 5 stars out of 5(27)

Johnston & Murphy - Hartford Plain Toe Boots. Color Tan Italian Calfskin. $327.95.

Tan Johnston & Murphy Hartford Plain Toe Boots

Tan Johnston & Murphy Hartford Plain Toe Boots

+3

Brand Name: Johnston & Murphy
Product Name: Hartford Plain Toe Boots
Gender: Men's
Color: Tan Italian Calfskin
Price: $327.95
Rating

Johnston & Murphy - Larkin Chukka. Color Tan Italian Calfskin. $158.95.

Tan Johnston & Murphy Larkin Chukka

Tan Johnston & Murphy Larkin Chukka

Brand Name: Johnston & Murphy
Product Name: Larkin Chukka
Gender: Men's
Color: Tan Italian Calfskin
Price: $158.95
Rating

Johnston & Murphy - Calder Chelsea Boots. Color Black Tumbled Full Grain. Low Stock. On sale for $119.99. MSRP $165.00. 27% off.

Low Stock

Black Johnston & Murphy Calder Chelsea Boots

Black Johnston & Murphy Calder Chelsea Boots

+2

Brand Name: Johnston & Murphy
Product Name: Calder Chelsea Boots
Gender: Men's
Color: Black Tumbled Full Grain
Price: $119.99MSRP: $165.0027% OFF
Rating

Clarks - Clarkspro Step. Color Dark Brown Tumbled Leather. On sale for $57.40. MSRP $140.00. 59% off. 3.0 out of 5 stars

Brown Clarks Clarkspro Step

Brown Clarks Clarkspro Step

Brand Name: Clarks
Product Name: Clarkspro Step
Gender: Men's
Color: Dark Brown Tumbled Leather
Price: $57.40MSRP: $140.0059% OFF
Rating: 3Rated 3 stars out of 5(7)

Dr. Martens - 2976 Quad Chelsea. Color Cherry Red. $210.00. 5.0 out of 5 stars

Red Dr. Martens 2976 Quad Chelsea

Red Dr. Martens 2976 Quad Chelsea

Brand Name: Dr. Martens
Product Name: 2976 Quad Chelsea
Gender: Unisex
Color: Cherry Red
Price: $210.00
Rating: 5Rated 5 stars out of 5(1)

Dr. Martens - Sinclair Leather Platform Boots. Color Dark Brown. $210.00.

Brown Dr. Martens Sinclair Leather Platform Boots

Brown Dr. Martens Sinclair Leather Platform Boots

Brand Name: Dr. Martens
Product Name: Sinclair Leather Platform Boots
Gender: Unisex
Color: Dark Brown
Price: $210.00
Rating

Dan Post - Albuquerque. Color Black. $198.00. 4.2 out of 5 stars

Black Dan Post Albuquerque

Black Dan Post Albuquerque

+2

Brand Name: Dan Post
Product Name: Albuquerque
Gender: Men's
Color: Black
Price: $198.00
Rating: 4Rated 4 stars out of 5(194)

Laredo - Nico. Color Taupe. $149.95.

Taupe Laredo Nico

Taupe Laredo Nico

Brand Name: Laredo
Product Name: Nico
Gender: Men's
Color: Taupe
Price: $149.95
Rating

Dan Post - Milwaukee R Toe. Color Black. On sale for $169.99. MSRP $199.95. 15% off. 4.2 out of 5 stars

Black Dan Post Milwaukee R Toe

Black Dan Post Milwaukee R Toe

Brand Name: Dan Post
Product Name: Milwaukee R Toe
Gender: Men's
Color: Black
Price: $169.99MSRP: $199.9515% OFF
Rating: 4Rated 4 stars out of 5(66)

Dr. Martens - Celestial Monk. Color Black. $170.00.

Black Dr. Martens Celestial Monk

Black Dr. Martens Celestial Monk

Brand Name: Dr. Martens
Product Name: Celestial Monk
Gender: Unisex
Color: Black
Price: $170.00
Rating

Dr. Martens - 1461 Quad II. Color Charcoal Grey. $169.95. 5.0 out of 5 stars

Gray Dr. Martens 1461 Quad II

Gray Dr. Martens 1461 Quad II

Brand Name: Dr. Martens
Product Name: 1461 Quad II
Gender: Unisex
Color: Charcoal Grey
Price: $169.95
Rating: 5Rated 5 stars out of 5(1)

Dr. Martens - Church Quad Archive. Color Dark Brown Crazy Horse. On sale for $120.00. MSRP $200.00. 40% off. 3.8 out of 5 stars

Brown Dr. Martens Church Quad Archive

Brown Dr. Martens Church Quad Archive

Brand Name: Dr. Martens
Product Name: Church Quad Archive
Gender: Unisex
Color: Dark Brown Crazy Horse
Price: $120.00MSRP: $200.0040% OFF
Rating: 4Rated 4 stars out of 5(4)

Corral Boots - C4175. Color Blue. Low Stock. $258.00.

Low Stock

Blue Corral Boots C4175

Blue Corral Boots C4175

Brand Name: Corral Boots
Product Name: C4175
Gender: Men's
Color: Blue
Price: $258.00
Rating

Frye - Harness 12R. Color Gaucho. Low Stock. $498.00. 4.6 out of 5 stars

Low Stock

Brown Frye Harness 12R

Brown Frye Harness 12R

Brand Name: Frye
Product Name: Harness 12R
Gender: Men's
Color: Gaucho
Price: $498.00
Rating: 5Rated 5 stars out of 5(200)

Johnston & Murphy - Brody Chukka. Color Snuff Suede. On sale for $92.40. MSRP $165.00. 44% off.

Brown Johnston & Murphy Brody Chukka

Brown Johnston & Murphy Brody Chukka

+2

Brand Name: Johnston & Murphy
Product Name: Brody Chukka
Gender: Men's
Color: Snuff Suede
Price: $92.40MSRP: $165.0044% OFF
Rating

Dan Post - Neeley. Color Tan. $229.95.

Tan Dan Post Neeley

Tan Dan Post Neeley

Brand Name: Dan Post
Product Name: Neeley
Gender: Men's
Color: Tan
Price: $229.95
Rating

Michael Kors - Atlas Boots. Color Luggage. Low Stock. On sale for $158.40. MSRP $288.00. 45% off.

Low Stock

Brown Michael Kors Atlas Boots

Brown Michael Kors Atlas Boots

Brand Name: Michael Kors
Product Name: Atlas Boots
Gender: Men's
Color: Luggage
Price: $158.40MSRP: $288.0045% OFF
Rating

Johnston & Murphy - Braxton Chukka. Color Brown Oiled Full Grain. $158.95.

Brown Johnston & Murphy Braxton Chukka

Brown Johnston & Murphy Braxton Chukka

Brand Name: Johnston & Murphy
Product Name: Braxton Chukka
Gender: Men's
Color: Brown Oiled Full Grain
Price: $158.95
Rating

PIKOLINOS - Olvera M8A-3189. Color Cuero. Low Stock. $185.00.

Low Stock

Tan PIKOLINOS Olvera M8A-3189

Tan PIKOLINOS Olvera M8A-3189

Brand Name: PIKOLINOS
Product Name: Olvera M8A-3189
Gender: Men's
Color: Cuero
Price: $185.00
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.)