Trend Watch
Back to the Classics
Old-school styles that breathe new life into your look.
Shop Now

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

Medium Size Leather Dress Gray Products

31 items found

Filters

Search Results

Johnston & Murphy - Upton Plain Toe. Color Gray Nubuck. On sale for $158.95. MSRP $169.00. 6% off. 4.4 out of 5 stars

Gray Johnston & Murphy Upton Plain Toe

Gray Johnston & Murphy Upton Plain Toe

+9

Brand Name: Johnston & Murphy
Product Name: Upton Plain Toe
Gender: Men's
Color: Gray Nubuck
Price: $158.95MSRP: $1696% OFF
Rating: 4Rated 4 stars out of 5(1393)

Kenneth Cole - Tully Cap Toe Oxford. Color Dark Grey Leather. On sale for $112.00. MSRP $159.95. 30% off. 4.5 out of 5 stars

Gray Kenneth Cole Tully Cap Toe Oxford

Gray Kenneth Cole Tully Cap Toe Oxford

+3

Brand Name: Kenneth Cole
Product Name: Tully Cap Toe Oxford
Gender: Men's
Color: Dark Grey Leather
Price: $112MSRP: $159.9530% OFF
Rating: 5Rated 5 stars out of 5(4)

PIKOLINOS - Bilbao M8D-4292C1. Color Dark Grey. $200.00.

Gray PIKOLINOS Bilbao M8D-4292C1

Gray PIKOLINOS Bilbao M8D-4292C1

Brand Name: PIKOLINOS
Product Name: Bilbao M8D-4292C1
Gender: Men's
Color: Dark Grey
Price: $200
Rating

Stacy Adams - Kaylor Penny Slip-On Loafer. Color Gray. Low Stock. On sale for $78.00. MSRP $130.00. 40% off. 4.7 out of 5 stars

Low Stock

Gray Stacy Adams Kaylor Penny Slip-On Loafer

Gray Stacy Adams Kaylor Penny Slip-On Loafer

Brand Name: Stacy Adams
Product Name: Kaylor Penny Slip-On Loafer
Gender: Men's
Color: Gray
Price: $78MSRP: $13040% OFF
Rating: 5Rated 5 stars out of 5(30)

Kenneth Cole - Charles. Color Dark Grey Leather. On sale for $143.95. MSRP $159.95. 10% off. 5.0 out of 5 stars

Gray Kenneth Cole Charles

Gray Kenneth Cole Charles

+2

Brand Name: Kenneth Cole
Product Name: Charles
Gender: Men's
Color: Dark Grey Leather
Price: $143.95MSRP: $159.9510% OFF
Rating: 5Rated 5 stars out of 5(2)

Stacy Adams - Brayden Wing Tip Lace-Up. Color Gray. Low Stock. On sale for $49.97. MSRP $145.00. 66% off. 4.4 out of 5 stars

Low Stock

Gray Stacy Adams Brayden Wing Tip Lace-Up

Gray Stacy Adams Brayden Wing Tip Lace-Up

+4

Brand Name: Stacy Adams
Product Name: Brayden Wing Tip Lace-Up
Gender: Men's
Color: Gray
Price: $49.97MSRP: $14566% OFF
Rating: 4Rated 4 stars out of 5(14)

Steve Madden - Hatton. Color Dark Grey. Low Stock. On sale for $119.00. MSRP $170.00. 30% off. 4.5 out of 5 stars

Low Stock

Gray Steve Madden Hatton

Gray Steve Madden Hatton

Brand Name: Steve Madden
Product Name: Hatton
Gender: Men's
Color: Dark Grey
Price: $119MSRP: $17030% OFF
Rating: 5Rated 5 stars out of 5(2)

Stacy Adams - Marligan Wing Tip Oxford. Color Dark Gray. On sale for $78.00. MSRP $130.00. 40% off. 4.7 out of 5 stars

Gray Stacy Adams Marligan Wing Tip Oxford

Gray Stacy Adams Marligan Wing Tip Oxford

+3

Brand Name: Stacy Adams
Product Name: Marligan Wing Tip Oxford
Gender: Men's
Color: Dark Gray
Price: $78MSRP: $13040% OFF
Rating: 5Rated 5 stars out of 5(23)

Allen Edmonds - Rand Verse Loafer/Moc Shoes. Color Vapor Suede. Low Stock. On sale for $349.00. MSRP $450.00. 22% off. 5.0 out of 5 stars

Low Stock

Gray Allen Edmonds Rand Verse Loafer/Moc Shoes

Gray Allen Edmonds Rand Verse Loafer/Moc Shoes

+6

Brand Name: Allen Edmonds
Product Name: Rand Verse Loafer/Moc Shoes
Gender: Men's
Color: Vapor Suede
Price: $349MSRP: $45022% OFF
Rating: 5Rated 5 stars out of 5(1)

Martin Dingman - Countryaire No Neoprene Wingtip. Color Smoke. Low Stock. On sale for $152.53. MSRP $295.00. 48% off.

Low Stock

Gray Martin Dingman Countryaire No Neoprene Wingtip

Gray Martin Dingman Countryaire No Neoprene Wingtip

Brand Name: Martin Dingman
Product Name: Countryaire No Neoprene Wingtip
Gender: Men's
Color: Smoke
Price: $152.53MSRP: $29548% OFF
Rating

Florsheim - Vibe Knit Plain Toe Oxford. Color Gray. On sale for $77.00. MSRP $110.00. 30% off. 4.7 out of 5 stars

Gray Florsheim Vibe Knit Plain Toe Oxford

Gray Florsheim Vibe Knit Plain Toe Oxford

+2

Brand Name: Florsheim
Product Name: Vibe Knit Plain Toe Oxford
Gender: Men's
Color: Gray
Price: $77MSRP: $11030% OFF
Rating: 5Rated 5 stars out of 5(85)

. Stacy Adams - Tarango Modified Cap Toe Oxford. Color Black/White. $115.00. 5.0 out of 5 stars

Gray Stacy Adams Tarango Modified Cap Toe Oxford

Gray Stacy Adams Tarango Modified Cap Toe Oxford

+5

Brand Name: Stacy Adams
Product Name: Tarango Modified Cap Toe Oxford
Gender: Men's
Color: Black/White
Price: $115
Rating: 5Rated 5 stars out of 5(1)

Allen Edmonds - Supersprtpen. Color Light Grey. Low Stock. $300.00. 4.0 out of 5 stars

Low Stock

Gray Allen Edmonds Supersprtpen

Gray Allen Edmonds Supersprtpen

Brand Name: Allen Edmonds
Product Name: Supersprtpen
Gender: Men's
Color: Light Grey
Price: $300
Rating: 4Rated 4 stars out of 5(1)

Steve Madden - Eckley. Color Grey Suede. Low Stock. $140.00.

Low Stock

Gray Steve Madden Eckley

Gray Steve Madden Eckley

+2

Brand Name: Steve Madden
Product Name: Eckley
Gender: Men's
Color: Grey Suede
Price: $140
Rating

Stacy Adams - Hallquist Plain Toe Lace-Up. Color Gray. Low Stock. On sale for $75.00. MSRP $150.00. 50% off. 4.0 out of 5 stars

Low Stock

Gray Stacy Adams Hallquist Plain Toe Lace-Up

Gray Stacy Adams Hallquist Plain Toe Lace-Up

+5

Brand Name: Stacy Adams
Product Name: Hallquist Plain Toe Lace-Up
Gender: Men's
Color: Gray
Price: $75MSRP: $15050% OFF
Rating: 4Rated 4 stars out of 5(4)

Stacy Adams - Winstead Saddle Slip-On. Color Natural. Low Stock. On sale for $112.50. MSRP $125.00. 10% off. 4.0 out of 5 stars

Low Stock

Gray Stacy Adams Winstead Saddle Slip-On

Gray Stacy Adams Winstead Saddle Slip-On

+3

Brand Name: Stacy Adams
Product Name: Winstead Saddle Slip-On
Gender: Men's
Color: Natural
Price: $112.50MSRP: $12510% OFF
Rating: 4Rated 4 stars out of 5(1)

Josef Seibel - Earl 05. Color Dark Grey/Kombi. $170.00. 4.0 out of 5 stars

Gray Josef Seibel Earl 05

Gray Josef Seibel Earl 05

+2

Brand Name: Josef Seibel
Product Name: Earl 05
Gender: Men's
Color: Dark Grey/Kombi
Price: $170
Rating: 4Rated 4 stars out of 5(9)

Blundstone - Aerocork™ Chelsea Boots. Color Texas Sand. $214.95.

Gray Blundstone Aerocork™ Chelsea Boots

Gray Blundstone Aerocork™ Chelsea Boots

+3

Brand Name: Blundstone
Product Name: Aerocork™ Chelsea Boots
Gender: Unisex
Color: Texas Sand
Price: $214.95
Rating

Nunn Bush - Chase 2.0 Casual Plain Toe Oxford Contemporary Lace-Up. Color Gray. On sale for $54.97. MSRP $90.00. 39% off. 3.9 out of 5 stars

Gray Nunn Bush Chase 2.0 Casual Plain Toe Oxford Contemporary Lace-Up

Gray Nunn Bush Chase 2.0 Casual Plain Toe Oxford Contemporary Lace-Up

+4

Brand Name: Nunn Bush
Product Name: Chase 2.0 Casual Plain Toe Oxford Contemporary Lace-Up
Gender: Men's
Color: Gray
Price: $54.97MSRP: $9039% OFF
Rating: 4Rated 4 stars out of 5(30)

Marc Joseph New York - Nebraska Loafer. Color Grey Suede. On sale for $89.95. MSRP $185.00. 51% off. 4.1 out of 5 stars

Gray Marc Joseph New York Nebraska Loafer

Gray Marc Joseph New York Nebraska Loafer

+8

Brand Name: Marc Joseph New York
Product Name: Nebraska Loafer
Gender: Men's
Color: Grey Suede
Price: $89.95MSRP: $18551% OFF
Rating: 4Rated 4 stars out of 5(21)

Cole Haan - 2.zerogrand Evo Laser Quick-on. Color Castlerock Nubuck/Raven. $179.95.

Gray Cole Haan 2.zerogrand Evo Laser Quick-on

Gray Cole Haan 2.zerogrand Evo Laser Quick-on

+4

Brand Name: Cole Haan
Product Name: 2.zerogrand Evo Laser Quick-on
Gender: Men's
Color: Castlerock Nubuck/Raven
Price: $179.95
Rating

Stacy Adams - Tristano Bike Toe Lace-Up. Color Black/Gray/White. On sale for $112.84. MSRP $115.00. 2% off. 4.5 out of 5 stars

Gray Stacy Adams Tristano Bike Toe Lace-Up

Gray Stacy Adams Tristano Bike Toe Lace-Up

+6

Brand Name: Stacy Adams
Product Name: Tristano Bike Toe Lace-Up
Gender: Men's
Color: Black/Gray/White
Price: $112.84MSRP: $1152% OFF
Rating: 5Rated 5 stars out of 5(6)

Florsheim - Motor Smooth Moc Toe Penny Driver. Color Gray. On sale for $98.95. MSRP $110.00. 10% off. 4.4 out of 5 stars

Gray Florsheim Motor Smooth Moc Toe Penny Driver

Gray Florsheim Motor Smooth Moc Toe Penny Driver

+7

Brand Name: Florsheim
Product Name: Motor Smooth Moc Toe Penny Driver
Gender: Men's
Color: Gray
Price: $98.95MSRP: $11010% OFF
Rating: 4Rated 4 stars out of 5(11)

Blundstone - Dress Chelsea Boots. Color Steel Grey Suede. $194.95. 4.0 out of 5 stars

Gray Blundstone Dress Chelsea Boots

Gray Blundstone Dress Chelsea Boots

+2

Brand Name: Blundstone
Product Name: Dress Chelsea Boots
Gender: Unisex
Color: Steel Grey Suede
Price: $194.95
Rating: 4Rated 4 stars out of 5(7)

Johnston & Murphy - Upton Knit Plain Toe. Color Gray Knit. On sale for $119.99. MSRP $159.00. 25% off. 4.1 out of 5 stars

Gray Johnston & Murphy Upton Knit Plain Toe

Gray Johnston & Murphy Upton Knit Plain Toe

+3

Brand Name: Johnston & Murphy
Product Name: Upton Knit Plain Toe
Gender: Men's
Color: Gray Knit
Price: $119.99MSRP: $15925% OFF
Rating: 4Rated 4 stars out of 5(71)

Nunn Bush - Otto Plain Toe Oxford. Color Gray. On sale for $79.95. MSRP $110.00. 27% off. 4.2 out of 5 stars

Gray Nunn Bush Otto Plain Toe Oxford

Gray Nunn Bush Otto Plain Toe Oxford

+4

Brand Name: Nunn Bush
Product Name: Otto Plain Toe Oxford
Gender: Men's
Color: Gray
Price: $79.95MSRP: $11027% OFF
Rating: 4Rated 4 stars out of 5(125)

Stacy Adams - Bryant Cap Toe Lace-Up. Color Gray. Low Stock. On sale for $109.95. MSRP $145.00. 24% off. 4.4 out of 5 stars

Low Stock

Gray Stacy Adams Bryant Cap Toe Lace-Up

Gray Stacy Adams Bryant Cap Toe Lace-Up

+3

Brand Name: Stacy Adams
Product Name: Bryant Cap Toe Lace-Up
Gender: Men's
Color: Gray
Price: $109.95MSRP: $14524% OFF
Rating: 4Rated 4 stars out of 5(32)

Naot - Bondos. Color Charcoal Suede. Low Stock. On sale for $131.97. MSRP $219.95. 40% off.

Low Stock

Gray Naot Bondos

Gray Naot Bondos

+3

Brand Name: Naot
Product Name: Bondos
Gender: Men's
Color: Charcoal Suede
Price: $131.97MSRP: $219.9540% OFF
Rating

To Boot New York - Christophe. Color Grey. Low Stock. On sale for $297.00. MSRP $495.00. 40% 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: $297MSRP: $49540% OFF
Rating

Kenneth Cole - Madison. Color Dark Grey Suede. $169.95.

Gray Kenneth Cole Madison

Gray Kenneth Cole Madison

+2

Brand Name: Kenneth Cole
Product Name: Madison
Gender: Men's
Color: Dark Grey Suede
Price: $169.95
Rating

PIKOLINOS - Berna M8J-4183. Color Topo. Low Stock. $200.00. 5.0 out of 5 stars

Low Stock

Gray PIKOLINOS Berna M8J-4183

Gray PIKOLINOS Berna M8J-4183

Brand Name: PIKOLINOS
Product Name: Berna M8J-4183
Gender: Men's
Color: Topo
Price: $200
Rating: 5Rated 5 stars out of 5(2)

Join Our Email List

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

*One code per email address.