It isn’t hard to understand why guys would want to find the most comfortable loafers on the market.
As a classic slip-on shoe, a good pair of loafers is one of the most timeless and stylish types of shoes a man can wear.
But they’re also a little risky, because even the best loafers can often leave you with sore feet and blisters (especially if you’re foregoing no show socks and going completely sockless).
Luxury shoes from big-name designers – like Prada, Ferragamo or Gucci loafers – are usually built for style first and comfort second, which means that investing in a high quality loafer is no guarantee of high comfort, even after the initial break-in period.
Fortunately, a lot of popular brands have (finally) realized that guys don’t particularly want a pair of shoes that leaves their foot a bloody mess, and today some of the best men’s loafers also happen to be the most comfortable.
To help you find the right loafers to suit your personal style, below I’ve rounded up some of the most comfortable loafers that will both enhance your appearance and forgive your feet.
The Most Comfortable Mens Loafers
Breaking Down the Most Comfortable Loafers for Men
Most Comfortable Mens Penny Loafers ↓
W&S Crossover Loafer
Features:
- 4.8 Stars
- 306 Reviews
- Available in 5 Colors
Advantages:
Combining the high-quality leather of dress shoes with the rubber soles of running shoes, Wolf & Shepherd not only makes some of the most comfortable shoes on the market, but some of the most stylish.
Their cross over penny loafers boast an Italian full-grain leather upper and have the kind of svelte toe shape you usually only find on the best dress shoes.
But down below, they’re all comfort, with a removable memory foam footbed and a high-traction, sneaker-like sole that makes them a great choice for everyday wear.
Before I tested these bad boys out for myself, I have to admit that I was a little skeptical of the crossover/hybrid loafer style.
But as I wrote in my full Wolf & Shepherd review, “Having the ability to slide on a pair of shoes and know that you’re not only going to be one of the best-dressed guys in any room, but also one of the most comfortable, is just incredibly empowering.”
Promising Review:
I got compliments the first time I wore these shoes. They do need a one-day break in period, but after that they are so comfortable that I can wear them all day. Great shoe, great comfort, excellent style.
– Tom S.
Most Comfortable Driving Shoes ↓
Cole Haan Grand Laser Driver
Features:
- 4.3 Stars
- 44 Reviews
- Available in 5 Colors
Advantages:
Another company that’s well known for making stylish and comfortable dress shoes, Cole Haan makes various types of loafers, including a particularly handsome pair of tassel loafers that are sharp as hell (at least in my opinion).
But when it comes to comfort, it’s damn near impossible to beat a good pair of drivers, which is why they’ve been one of the most essential casual shoes for decades—and why Cole Haan’s “Grand Lasers” edged out the tassels for inclusion in this list.
These classic leather loafers boast the timeless look that drivers are known for, with a slightly rounded toe that’s decidedly more casual than the elegant design of dressier shoes.
But more to the point, they also come with a leather footbed that provides arch support and increased cushioning, along with the eponymous laser patterning (aka the small holes that dot the top of the shoe’s toe box), which provide breathability and make these some of the best shoes to wear during hot summer months.
Most Comfortable Mens Dress Loafers ↓
J&M Meade Penny
Features:
- 4.3 Stars
- 14 Reviews
- Available in 2 Colors
Advantages:
Whereas the drivers above are the kind of humble loafer you’d pair with shorts or blue jeans, this stylish shoe from Johnston & Murphy is more refined, making it more appropriate for the kind of special occasion that calls for formal wear.
(But it’s worth noting that penny loafers are generally considered too informal for a proper black-tie event, where you usually want something in patent leather.)
They’re made of hand-finished Italian leather, but don’t let the high quality material fool you; the good news here is that their sharp style doesn’t come at the cost of comfort.
The Meades have a molded, cushioned insole that provides plenty of comfort, and the outsoles have two rubber pads that provide better grip than traditional leather soles.
Promising Review:
I wear these when I go on business trips and on client sites. I can be on my feet for 8 hours with no problems at all. Super comfortable and still stylish!
– Michael
Most Comfortable Mens Casual Loafers ↓
Amberjack Loafers
Features:
- 4.8 Stars
- 88 Reviews
- Available in 7 Colors
Advantages:
If you’re looking for a comfortable pair of go-to loafers that you can wear to the office, the pub or damn near anywhere else, look no further.
Stylewise, Amberjack’s laceless slip-ons have the kind of versatility that lets you pair them with anything:
They look great with a pair of jeans and a polo on the weekend, work just as well with khakis and an oxford shirt at your business casual office, and can even be paired with a suit at semi formal events.
And the comfort level is second to none. They’re made with a dual-density athletic outsole and heat-activated insole, which combine to provide the kind of comfort you usually only get from athletic shoes.
Promising Review:
I love the loafers and have two pairs – black and slate. They are comfortable, and the classic good looks match most of my wardrobes. Impressive construction and material quality!
– TYeah
Most Comfortable Mens Loafers For Walking ↓
W&S Swiftknit Loafer
Features:
- 4.9 Stars
- 328 Reviews
- Available in 3 Colors
Advantages:
The second model from Wolf & Shepherd to crack our top five, the Swiftknit loafer is a slip-on sneaker with the svelte toe shape of a dress shoe.
It’s become a popular choice within the menswear world for guys who spend a long time on their feet, but want something more stylish than a pair of Asics.
Like the W&S penny loafers above, it’s made from premium materials and has the same high-density TPU midsole and removable memory foam footbed.
But with a breathable polyester upper, this one also has the kind of lightweight, soft construction that makes it easy to wear (and walk) for hours on end.
Promising Review:
I love this shoe! I have two pair that I wear to work as a nurse practitioner and get compliments from patients almost daily. Very comfortable for long days on my feet!
– Charles R.
Best of the Rest
The five loafers above represent our top picks for the highest quality and most comfortable men’s loafers on the market, but they’re hardly the only ones worth considering.
To give you a wider variety of options, below we’ve rounded up nearly a dozen more supportive and stylish loafers that combine comfort, style and a great price range.
And if you’re looking to go beyond loafers, check out our round-up of the most comfortable men’s dress shoes that are so supportive they feel more like sneakers than proper dress shoes.
Clarks Gorwin Step
Features:
- 5 Stars
- 2 Reviews
- Available in 8 Colors
Promising Review:
I bought these several weeks ago after looking and looking for comfortable, casual but nice slip on. I FOUND IT! There was absolutely no break in period. I can wear these all day and walk all over town.
They’re as comfortable at the end of the day as they are at the beginning. I really love these shoes and they’re at the perfect price point.
– Jeff L.
J&M Upton Venetian
Features:
- 5 Stars
- 1 Reviews
- Available in 3 Colors
Promising Review:
Very comfortable throwback look from many years ago… They look great with any pants or shorts, complimenting the casual no socks look and the leather is soft.
– LJ
W&S Monaco Loafer
Features:
- 4.8 Stars
- 142 Reviews
- Available in 3 Colors
Promising Review:
Super dooper comfortable. Can walk in them all day without your feet hurting. Definitely not a “formal” loafer. I wear them with jeans or shorts usually. Super easy to wear.
– Len
J&M McGuffey Woven Slip-On
Features:
- 5 Stars
- 848 Reviews
- Available in 5 Colors
Promising Review:
I love these shoes! This is my 2nd pair. I have the tan color and recently purchased them in black. I always get compliments on the shoes!
They are extremely comfortable and can be word with slacks or jeans.
– Dennis
Clarks Gorwin Moc
Features:
- 5 Stars
- 1 Reviews
- Available in 3 Colors
Promising Review:
My husband loves these shoes, and he’s extremely picky. They fit well and are very very comfortable. He loves them so much, he bought two pair.
– Hollieheart
Hush Puppies Julian Loafer
Features:
- 4.5 Stars
- 2 Reviews
- Available in 2 Colors
Promising Review:
Very comfortable. Good fit, accurate size and look great!
– HP
Rockport Classic Penny Loafer
Features:
- 4.4 Stars
- 3,763 Reviews
- Available in 9 Colors
Promising Review:
I needed a shoe that was somewhere between formal and too casual. This fit the bill. Great for the office and with a blazer. Comfortable AF.
– Dave Peterson
Hush Puppies Bennet Plain Toe Slip On
Features:
- 4.3 Stars
- 53 Reviews
- Available in 3 Colors
Promising Review:
Outstanding in every way. Great looking, well made, light weight and incredibly comfortable.
– Mike
G.H. Bass Weejuns
Features:
- Available in dozens of styles and colors
Did you know…?
James Dean, one of the most classic men’s style icons of the past century, wore these iconic brown loafers from G.H Bass & Co in Rebel Without a Cause.
Rockport Classic Lite Venetian
Features:
- 4.3 Stars
- 1,542 Reviews
- Available in 3 Colors
Promising Review:
These loafers are very comfortable and feel well made. Good quality leather, stitching and nice color.
– Roy
More Resources ↓
More Advice on Men’s Boots and Shoes from Irreverent Gent:
- The Best Running Shoes for Morton’s Neuroma
- The Absolute Best Chef Shoes for Professional Kitchens
- The Best Men’s Shoes to Wear with Jeans
- The Absolute Best Shoes to Wear with Shorts
- The Most Stylish Men’s Casual Boots to Wear with Jeans
- 9 Stylish & Comfortable Dress Shoes That Feel Like Sneakers
- The Absolute Best Men’s Shoes for Standing All Day
- The 25 Best Men’s Summer Shoes
- The Best Nursing Shoes for Men
- The 8 Most Stylish Types of Men’s Shoes
- The (Absolute) Best Casual Shoes for Men
- The Best Men’s Shoes for Plantar Fasciitis
- 17 of the Best Men’s Chukka Boots
- In Review: Beckett Simonon Shoes
- The 31 Best Shoes for Walking on Concrete All Day
- How to
WearRock a Blue Suit and Brown Shoes - The Most Comfortable Work Boots on the Market
- In Review: Thursday Boot Company’s “Captain”
- The 9 Best Boot Styles for Men
- The (Absolute) Best Mens Fall Shoes
- The Best Red Wing Boots for Men to Wear Daily
- The Most Stylish, Comfortable & Best Shoes for Male Teachers
- In Review: Johnston & Murphy Karnes Cap Toe Boot
- The Most Comfortable Golf Shoes for Walking the Course
- The 11 Most Comfortable Steel Toe Boots for Standing All Day
- In-Depth Wolf and Shepherd Shoes Review
- The Best Men’s White Sole Dress Shoes
- The Most Comfortable White Sneakers for Men
- The (Absolute) Best Men’s Dress Shoe Brands
The Recap ↓
W&S Crossover Loafer
Cole Haan Grand Laser Driver
J&M Meade Penny
Amberjack Loafers
Summary
A lot of popular brands have (finally) realized that guys don’t particularly want a pair of shoes that leaves their foot a bloody mess, and today some of the best men’s loafers also happen to be the most comfortable.
Banner Image: Wolf & Shepherd, Illustration by Irreverent Gent
