Free Shipping on Orders $89+ With Code: SHIP89. See Details.
  1. Shoes
  2. Men's Shoes
  3. Men's Comfortable Shoes
  4. (46 items)
Loading
  •  
  • Per page: 24 | 96
Alpargata Canvas Shoes (For Men) in Ash
Quick View
Show Brand TOMS
Alpargata Canvas Shoes (For Men)
$24.99
Compare at $49.95
Save 49%
5.0 out of 5 stars. 0 reviews for TOMS Alpargata Canvas Shoes (For Men)
Classic Alpargata REPREVE® Knit Shoes (For Men) in Black
Quick View
Show Brand TOMS
Classic Alpargata REPREVE® Knit Shoes (For Men)
$24.99
Compare at $54.95
Save 54%
5.0 out of 5 stars. 0 reviews for TOMS Classic Alpargata REPREVE® Knit Shoes (For Men)
Merrell Jungle Moc Rinse Shoes - Suede, Slip-Ons (For Men) in Bracken
Quick View
Merrell
Jungle Moc Rinse Shoes - Suede, Slip-Ons (For Men)
$49.99
Compare at $80.00
Save 37%
5.0 out of 5 stars. 0 reviews for Merrell Jungle Moc Rinse Shoes - Suede, Slip-Ons (For Men)
Kodiak Skogan Low-Cut Hiking Shoes - Waterproof (For Men) in Gold/Blue
Quick View
Kodiak
Skogan Low-Cut Hiking Shoes - Waterproof (For Men)
$49.99
Compare at $140.00
Save 64%
5.0 out of 5 stars. 0 reviews for Kodiak Skogan Low-Cut Hiking Shoes - Waterproof (For Men)
ROAN BY BED STU Remi Shoes - Suede (For Men) in Light Brown
Quick View
ROAN BY BED STU
Remi Shoes - Suede (For Men)
$29.99
Compare at $70.00
Save 57%
5.0 out of 5 stars. 0 reviews for ROAN BY BED STU Remi Shoes - Suede (For Men)
ITALIA DIFFERENCE Made in Italy Penny Loafers - Leather (For Men) in Brown
Quick View
ITALIA DIFFERENCE
Made in Italy Penny Loafers - Leather (For Men)
$49.99
Compare at $90.00
Save 44%
5.0 out of 5 stars. 0 reviews for ITALIA DIFFERENCE Made in Italy Penny Loafers - Leather (For Men)
ITALIA DIFFERENCE Made in Italy Penny Loafers - Leather (For Men) in Black
Quick View
ITALIA DIFFERENCE
Made in Italy Penny Loafers - Leather (For Men)
$49.99
Compare at $90.00
Save 44%
5.0 out of 5 stars. 0 reviews for ITALIA DIFFERENCE Made in Italy Penny Loafers - Leather (For Men)
Sperry A/O 2-Eye PLUSHWAVE Boat Shoes - Leather, Wide Width (For Men) in Navy
Quick View
Sperry
A/O 2-Eye PLUSHWAVE Boat Shoes - Leather, Wide Width (For Men)
$49.99
Compare at $80.00
Save 37%
5.0 out of 5 stars. 0 reviews for Sperry A/O 2-Eye PLUSHWAVE Boat Shoes - Leather, Wide Width (For Men)
The North Face Larimer Lace Approach Shoes (For Men) in Athletic Empathy/Tnf Black
Quick View
The North Face
Larimer Lace Approach Shoes (For Men)
$49.99
Compare at $90.00
Save 44%
5.0 out of 5 stars. 0 reviews for The North Face Larimer Lace Approach Shoes (For Men)
Sperry Authentic Original Seacycled 2-Eye Boat Shoes (For Men) in Natural Tan
Quick View
Sperry
Authentic Original Seacycled 2-Eye Boat Shoes (For Men)
$39.00
Compare at $80.00
Save 51%
5.0 out of 5 stars. 0 reviews for Sperry Authentic Original Seacycled 2-Eye Boat Shoes (For Men)
Clearance
ENZO TESOTI Made in Spain Boat Shoes - Leather (For Men) in Brown
Quick View
ENZO TESOTI
Made in Spain Boat Shoes - Leather (For Men)
$34.99
Compare at $60.00
Save 41%
5.0 out of 5 stars. 0 reviews for ENZO TESOTI Made in Spain Boat Shoes - Leather (For Men)
ENZO TESOTI Made in Spain Driver Moccasin Penny Loafers - Nappa Leather (For Men) in Black
Quick View
ENZO TESOTI
Made in Spain Driver Moccasin Penny Loafers - Nappa Leather (For Men)
$34.99
Compare at $60.00
Save 41%
5.0 out of 5 stars. 0 reviews for ENZO TESOTI Made in Spain Driver Moccasin Penny Loafers - Nappa Leather (For Men)
ROAN BY BED STU Remi Loafers - Suede (For Men) in Bone
Quick View
ROAN BY BED STU
Remi Loafers - Suede (For Men)
$29.99
Compare at $70.00
Save 57%
5.0 out of 5 stars. 0 reviews for ROAN BY BED STU Remi Loafers - Suede (For Men)
JoyBees Varsity Clogs (For Men) in Solid Navy
Quick View
JoyBees
Varsity Clogs (For Men)
$16.99
Compare at $24.00
Save 29%
5.0 out of 5 stars. 0 reviews for JoyBees Varsity Clogs (For Men)
Kodiak Skogan Low-Cut Hiking Shoes - Waterproof (For Men) in Gold/Blue
Quick View
Kodiak
Skogan Low-Cut Hiking Shoes - Waterproof (For Men)
$39.00
Compare at $140.00
Save 72%
5.0 out of 5 stars. 0 reviews for Kodiak Skogan Low-Cut Hiking Shoes - Waterproof (For Men)
Clearance
ENZO TESOTI Made in Spain Driver Moccasin Loafers - Nappa Leather (For Men) in Brown
Quick View
ENZO TESOTI
Made in Spain Driver Moccasin Loafers - Nappa Leather (For Men)
$34.99
Compare at $60.00
Save 41%
5.0 out of 5 stars. 0 reviews for ENZO TESOTI Made in Spain Driver Moccasin Loafers - Nappa Leather (For Men)
ECCO Street Lite Shoes - Leather, Slip-Ons (For Men) in Taupe
Quick View
ECCO
Street Lite Shoes - Leather, Slip-Ons (For Men)
$39.99
Compare at $70.00
Save 42%
5.0 out of 5 stars. 0 reviews for ECCO Street Lite Shoes - Leather, Slip-Ons (For Men)
B-52 by Bullboxer Tresel Clogs - Faux-Fur Lined (For Men) in Oliv Olive
Quick View
B-52 by Bullboxer
Tresel Clogs - Faux-Fur Lined (For Men)
$29.00
Compare at $60.00
Save 51%
5.0 out of 5 stars. 0 reviews for B-52 by Bullboxer Tresel Clogs - Faux-Fur Lined (For Men)
Clearance
JoyBees Varsity Clogs (For Men) in Solid Charcoal
Quick View
JoyBees
Varsity Clogs (For Men)
$16.99
Compare at $24.00
Save 29%
5.0 out of 5 stars. 0 reviews for JoyBees Varsity Clogs (For Men)
Classic Alpargata Canvas Shoes (For Men) in Red
Quick View
Show Brand TOMS
Classic Alpargata Canvas Shoes (For Men)
$20.00
Compare at $49.95
Save 59%
5.0 out of 5 stars. 0 reviews for TOMS Classic Alpargata Canvas Shoes (For Men)
Clearance
Earth Elements Anton Mesh Knit Sneakers (For Men) in Denim/Yellow/Cream
Quick View
Earth Elements
Anton Mesh Knit Sneakers (For Men)
$20.00
Compare at $35.00
Save 42%
5.0 out of 5 stars. 0 reviews for Earth Elements Anton Mesh Knit Sneakers (For Men)
Clearance
Earth Elements Cullen Knit Sneakers (For Men) in Silver Grey
Quick View
Earth Elements
Cullen Knit Sneakers (For Men)
$20.00
Compare at $35.00
Save 42%
5.0 out of 5 stars. 0 reviews for Earth Elements Cullen Knit Sneakers (For Men)
Clearance
Merrell Jungle Moc Rinse Shoes - Suede, Slip-Ons (For Men) in Gunsmoke
Quick View
Merrell
Jungle Moc Rinse Shoes - Suede, Slip-Ons (For Men)
$39.00
Compare at $70.00
Save 44%
5.0 out of 5 stars. 0 reviews for Merrell Jungle Moc Rinse Shoes - Suede, Slip-Ons (For Men)
Clearance
Twisted X Boots Crossover Shoes - Leather, Slip-Ons (For Men) in Bomber
Quick View
Twisted X Boots
Crossover Shoes - Leather, Slip-Ons (For Men)
$49.99
Compare at $120.00
Save 58%
5.0 out of 5 stars. 0 reviews for Twisted X Boots Crossover Shoes - Leather, Slip-Ons (For Men)
New

NEXT PAGE

About Men's Comfortable Shoes

You know what they say: comfort is king. Or at least, that's what we say at Sierra—especially when it comes to shoes. So if you're seeking comfortable shoes for men, you can relax right here. Boat shoes and loafers let everyone know that you keep it classy when you kick back, while men's moccasins or clogs are ideal for low-key days at home. Our wide selection of comfortable slip-ons are perfect when you need to get your shoes on in a hurry—like when you're racing outside to grab a freshly-delivered package from Sierra. And with these prices, that might start happening a lot.