Filters

Men
Penny
Get it Fast
5 5.5 6 6.5 7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 12.5 13 13.5 14 14.5 15 15.5 16 44
Get it Fast
110 Results
  1. Home
    /
  2. Men's
    /
  3. Men's Shoes
  1. Men's
  1. Home
    /
  2. Men's
    /
  3. Men's Shoes
  1. Men's

Men's Penny Shoes

110 Results
product image

Vince Camuto
Varrak Penny Loafer

Now $79.99
$100.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(4)
product image

Florsheim
Rucci Penny Loafer

Now $109.99
$145.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(28)
product image

Rockport
Classic Penny Loafer

Now $89.99
$125.00 Comp. value
★★★★★ ★★★★★
(553)
product image

Cole Haan
Nantucket Drift Penny Loafer

Now $99.99
$130.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(3)
product image

Steve Madden
Payton Loafer

Now $99.99
$120.00 Comp. value
Extra 25% off reg. price!
product image

Cole Haan
Pinch Prep Penny Loafer - Men's

Minimum Clearance Price $104.98 $104.98 – Maximum Clearance Price $129.99 $129.99
$238.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(32)
New Arrival
product image

Mix No. 6
Kenedy Penny Loafer

$59.99
Extra 25% off reg. price!
Clearance
product image

Vince Camuto
Utaro Penny Loafer

Minimum Clearance Price $59.98 $59.98
Clearance Item - Original Price $69.99 $69.99
Extra 25% off reg. price!
★★★★★ ★★★★★
(2)
product image

Steve Madden
Dalton Penny Loafer

Minimum Clearance Price $74.98 $74.98 – Maximum Clearance Price $99.99 $99.99
$120.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(1)
product image

Steve Madden
Zeb Penny Loafer - Men's

$109.99
Extra 25% off reg. price!
★★★★★ ★★★★★
(16)
product image

Nunn Bush
Lincoln Penny Loafer - Men's

Now $79.99
$100.00 Comp. value
Extra 25% off reg. price!
product image

Cole Haan
Newmark Grand Penny Loafer

Now $139.99
$308.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(1)
product image

Vance
Yates Penny Loafer

Now $59.99
$90.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(8)
Clearance
product image

Vince Camuto
Esmail Driving Loafer

Minimum Clearance Price $64.98 $64.98
$100.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(308)
product image

Florsheim
Motor Driving Loafer

Now $89.99
$110.00 Comp. value
★★★★★ ★★★★★
(1)
product image

TAFT
Jack Penny Loafer

$274.99
Extra 25% off reg. price!
★★★★★ ★★★★★
(15)
Clearance
product image

Birkenstock
Naple Penny Loafer - Men's

Minimum Clearance Price $109.98 $109.98
$160.00 Comp. value
Limited time! Up to 30% off
Clearance
product image

Mix No. 6
Cairro Loafer

Minimum Clearance Price $39.98 $39.98 – Maximum Clearance Price $49.98 $49.98
$80.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(8)
product image

Nunn Bush
Noah Penny Loafer

Now $89.99
$110.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(22)
product image

Vionic
Uptown Loafer - Men's

$179.99
★★★★★ ★★★★★
(20)
product image

Florsheim
Berkley Penny Loafer

Now $129.99
$145.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(305)
product image

Nunn Bush
Carmelo Penny Loafer

Now $64.99
$90.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(1)
product image

Rockport
Wilcox Penny Loafer

Now $99.99
$130.00 Comp. value
product image

Florsheim
Motor Penny Driving Loafer

Minimum Clearance Price $74.98 $74.98 – Maximum Clearance Price $89.99 $89.99
$110.00 Comp. value
★★★★★ ★★★★★
(6)
product image

TAFT
Luke Driving Moccasin

$249.99
Extra 25% off reg. price!
★★★★★ ★★★★★
(14)
product image

Nunn Bush
Drexel Penny Loafer

Now $89.99
$110.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(15)
product image

Nunn Bush
Odin II Penny Loafer

Now $89.99
$110.00 Comp. value
Extra 25% off reg. price!
product image

Florsheim
Motor Penny Loafer

Now $89.99
$110.00 Comp. value
Extra 25% off reg. price!
product image

Rockport
Soren Penny Loafer

Now $99.99
$130.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(1)
product image

Carlos by Carlos Santana
Ritchie Penny Loafer

$128.99
Extra 25% off reg. price!
★★★★★ ★★★★★
(14)
product image

Steve Madden
Boca Penny Loafer

$139.99
★★★★★ ★★★★★
(1)
product image

Rockport
Cory Penny Loafer

Now $109.99
$140.00 Comp. value
★★★★★ ★★★★★
(2)
product image

Vionic
Thompson Penny Loafer - Men's

$179.99
★★★★★ ★★★★★
(41)
product image

Cole Haan
Nantucket Drift Penny Loafer

Now $99.99
$130.00 Comp. value
Extra 25% off reg. price!
product image

Calvin Klein
Magnus Penny Loafer

Now $109.99
$135.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(42)
New Arrival
product image

Stacy Adams
Everett Penny Loafer

Now $99.99
$110.00 Comp. value
Extra 25% off reg. price!
product image

A. Veer
Cairo Loafer

$158.99
Extra 25% off reg. price!
product image

Dockers
Pembroke Penny Loafer

Now $64.99
$90.00 Comp. value
Extra 25% off reg. price!
product image

Born
Davis Penny Loafer

$134.99
Extra 25% off reg. price!
★★★★★ ★★★★★
(1)
product image

Vance
Phineas Penny Loafer

Now $69.99
$100.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(3)
New Arrival
product image

Brooks Brothers
Glenrock Penny Loafer

$198.99
product image

Vance
Brantley Penny Loafer

Now $69.99
$100.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(1)
product image

Guess
Symon Penny Loafer

Now $79.99
$109.00 Comp. value
Extra 25% off reg. price!
product image

Rockport
Cory Penny Loafer

Now $109.99
$140.00 Comp. value
★★★★★ ★★★★★
(1)
product image

Stacy Adams
Spencer Penny Loafer

Now $74.99
$130.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(1)
Clearance
product image

Steve Madden
Zionn Penny Loafer

Minimum Clearance Price $89.98 $89.98
$140.00 Comp. value
Extra 25% off reg. price!
product image

Johnston & Murphy
Tyson Penny Loafer

$168.99
★★★★★ ★★★★★
(3)
product image

TAFT
Sterling Loafer

Now $229.99
$295.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(10)
Clearance
product image

Cole Haan
Nantucket Loafer

Minimum Clearance Price $69.98 $69.98
$150.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(27)
product image

Anthony Veer
Belmont Penny Loafer

$278.99
Extra 25% off reg. price!
product image

Brooks Brothers
Glenrock Loafer

$198.99
★★★★★ ★★★★★
(1)
product image

Anthony Veer
Como Penny Loafer

$278.99
Extra 25% off reg. price!
product image

A. Veer
Mason Penny Loafer

$148.99
Extra 25% off reg. price!
product image

A. Veer
Jasper Loafer

$138.99
Extra 25% off reg. price!
product image

Florsheim
Zaffiro Penny Loafer

$144.99
Extra 25% off reg. price!
★★★★★ ★★★★★
(1)
New Arrival
product image

Dockers
Blair Penny Loafer

Now $64.99 – Maximum Clearance Price $89.99 $89.99
$90.00 Comp. value
Extra 25% off reg. price!
product image

Steve Madden
Natan Penny Loafer

$139.99
★★★★★ ★★★★★
(10)
Clearance
product image

Hush Puppies
Leo Penny Loafer

Minimum Clearance Price $49.98 $49.98 – Maximum Clearance Price $64.98 $64.98
$110.00 Comp. value
Extra 25% off reg. price!
★★★★★ ★★★★★
(14)
product image

Carlos by Carlos Santana
Nocturne Penny Loafer

$178.99
Extra 25% off reg. price!
product image

Stacy Adams
Hayes Penny Loafer

Now $109.99
$120.00 Comp. value
Extra 25% off reg. price!