In this article, we’ll discuss what we think are the best penny loafers that men can buy.
The best penny loafers can be challenging to find. You can easily be overwhelmed by all of the options available. Of course, it’s also hard to know which shoes will be comfortable and which will give you blisters before noon.
Luckily, I’ve done the work for you! As a stylist, I always search for the most stylish, comfortable accessories. Consider this TMM’s Guide to the best penny loafers of 2023.
Here are our recommendations from the list:
Brunello Cucinelli offers the finest black leather penny loafers for a discreetly luxurious style, perfect for pairing with denim, and they have a true-to-size fit.
Read on for more info and the complete list…
The Best Penny Loafers Under $200
If you’re seeking an affordable option for the best penny loafers, check out my picks below. These stylish shoes won’t break the bank.
Since these are under $200, they don’t have quite the quality or craftsmanship of the more expensive options. These are still decent shoes that will make you look and feel great.
Florsheim Men’s Throttle Moc Penny Loafer
These penny loafers have a leather upper and a comfortable lug sole for great traction and durability. They’re also an incredible deal at under $100 on Amazon.
These loafers are available in black and two shades of brown. Consider ordering your usual size and a half size down to compare.
Bloomingdales’ Mens Penny Loafer Drivers
Personally, these are my favorite casual penny loafers for men.
The suede upper and rubber sole make a comfortable, stylish shoe that pairs well with chino shorts. Offered in navy, black, and tan suede, these fit true to size.
G.H. Bass Larson Weejuns Penny Loafer
You can’t talk about the best penny loafers without mentioning the original, G.H. Bass.
This classic shoe we’ve already featured right here on TMM. It remains a favorite for a reason.
Since they’re leather shoes, they may stretch with wear. Order a half size down.
Wolf and Shepherd Monaco Loafer
The Los Angles based shoe company Wolf and Shepherd designs dress shoes with the comfort of athletic
This style offers a waterproof upper in Italian suede. Their FloatForm memory foam footbed means you can wear these all day long.
However, they are slightly narrow. Skip these if you have a normal or wider foot. If you’re on the narrow side, these might be the best penny loafers for you.
Cole Haan Men’s Pinch Penny Slip-On Loafer
Cole Haan offers a great dressy penny loafer at an outstanding price.
These run true to size. If you have a wider foot, though, I recommend ordering a half size up as well as your normal size to compare.
Sandro Moscholoni Antoine Penny Loafer
Do you need an affordable option in brown or navy?
This is one of the best penny loafers to wear without socks. Pair them with cuffed jeans or rolled chinos.
These fit true to size. Order your normal shoe size.
The Best Penny Loafers for Men Under $500
Regarding fashion, this contemporary category sits in the middle of the pricing scale. These styles are more expensive than the affordable options above but still under $500.
As you might expect, they’re higher quality than the budget options. In other words, you’re likely to get more bang for your buck.
Idrese Greene Loafers
If you want the designer look but aren’t ready to spend four figures on your feet, look no further than these Idrese loafers. The brown suede construction is a perfect wardrobe addition for fall.
Like all the best penny loafers, they’re handmade in Spain right alongside Ferragamos. They fit true to size. They’re even available in Wide (EE) widths. These might just be the best penny loafers for wide feet.
Banana Republic Asher Suede Penny Loafers
Have you heard? Banana Republic is good again! They’ve got some of the best penny loafers this summer.
These have suede uppers and leather soles. Get the lighter stone gray for this season and the tobacco brown for fall.
For any lighter shoes, I recommend cleaning and spraying them with weather protectant as soon as you take them out of the box. These run true to size.
Jack Erwin Luke Penny Loafer
This traditional dress loafer offers a reinforced stacked heel.
They’re handcrafted in Spain with full-grain leather or suede. These run true to size.
Beckett Simon Cohen Penny Loafers
While they might be better known for the Beckett Simon Bernard Tassel Loafers, their Cohen Penny Loafers shouldn’t be overlooked.
They’ve got six color options, including Bordeaux, which is my personal favorite.
I recommend sizing up by a half size if you have a wider foot.
Jay Butler Cromwell Penny Loafers
These brown leather penny loafers offer the quality of Italian footwear with American styling sensibilities. Reach for these loafers when you’re creating an upscale casual look.
While these run true to size, I recommend sizing up by half if you’ve got a wide foot.
Allen Edmonds Comfort Slip-On Penny Loafer
These are some of the best penny loafers to take you from work to weekend.
They’re comfortable and stylish enough for both the office and social events.
These fit true to size, so you can feel confident ordering your normal shoe size.
VINNYS Richee Penny Loafer
I am digging these two-tone shoes for the avant-garde, the artist, or the punk in a penny loafer. They have a leather upper and comfortable lug soles in rubber.
I can’t imagine them not looking good with cropped, grey plaid pants. Of course, the chunky platform sole will also give you a bit of height. These only come in whole sizes. So go up one if you’re in between.
Blackstock & Weber The Ellis Penny Loafer
If the black and white pair above offer too much contrast or don’t pair well with the rest of your wardrobe, consider this taupe and white version.
These run large, so order a full size down.
Magnanni Men’s Sasso Leather Penny Loafers
It’s hard to believe, but these look even better in person. The leather is gorgeous.
While these sit at the top of this price range, they’re worth it.
If it’s your first time ordering them, I recommend ordering a half size down from your usual size. I refuse to be responsible for starting your Magnanni addition, though.
The Best Penny Loafers For Men Over $500
If you’re ready to invest in your image, look to upgrade your shoes. While spending $500 or more on a pair of shoes isn’t for everybody, here are some luxury options.
Alden Men’s Leisure Hand Sewn Cordovan Penny Loafers
Alden is a beloved men’s shoe brand. As the only remaining New England shoe manufacturer, their quality and craftsmanship are stellar.
A pair of Aldens lasts for many years and is comfortable right out of the box.
These fit true to size.
Ferragamo Men’s Goyamvit Best So Slip On Penny Loafers
While Gucci loafers tend to get all the love, these penny loafers from Ferragamo are my pick for the best men’s loafers.
The leather upper, lining, and sole scream quality Italian craftsmanship.
These fantastic men’s shoes run true to size.
Brunello Cucinelli Men’s Leather Penny Loafers
These are the best penny loafers if you’re seeking the ultimate in quiet luxury.
From “stealth wealth brand” Brunello Cucinelli, this is one of the rare black leather penny loafers that, in my opinion, look good with denim.
These fit true to size.
Christian Louboutin No Penny Patent Leather Penny Loafers
And for those of you who still prefer your luxury on the loud side, check out these impeccable Louboutins. With that sleek patent leather and the iconic red sole, all eyes will be on you.
Wear with caution. I think they call these the no penny because when you wear them, you’re a dime. They run true to size.
Thom Browne Varsity Penny Loafers
I love that these Thom Browne loafers offer a more pointed toe than a traditional penny loafer. This helps elongate your lower half.
Comprised of a leather upper, lining, and sole, they’re made in Italy. These fit true to size.
Here are answers to some common questions about penny loafers:
What Are the Most Famous Penny Loafers?
In 1936, shoemaker G.H. Bass brought the Norweigan Fisherman’s shoe to America, calling it a penny loafer. The brand still makes its signature shoes today.
What brand is known for loafers?
American shoemaker G.H. Bass invented penny loafers in 1936. However, in 2023, Gucci, the Italian fashion house, is well known for its horse-bit loafers.
Are penny loafers still in style in 2023?
Yes. Men’s penny loafers are a classic wardrobe staple. For preppy, dressy, and casual looks, penny loafers are still in style.
Which loafers did Michael Jackson wear?
Micahel Jackson wore the G.H. Bass Larson Weejuns with white socks for his signature looks. The same exact loafers were also JFK’s favorite leisure shoe. See? Penny Loafers have a range.
Which are the best men’s penny loafers?
While G.H. Bass is the brand that created the iconic loafer shoe in the 1930s, it doesn’t mean it’s the best loafer for you. The best penny loafers depend on your lifestyle, budget, and taste. That said, I’m confident that a shoe on this list can work for you.
Final Thoughts on the Best Penny Loafers
Depending on your budget and lifestyle, there are several great options for the best penny loafers.
Loafers are great because work with both casual and dressy looks. Pair them with chinos, shorts, rolled-up jeans, cuffed slacks, and cropped suits.
Honestly, penny loafers will never go out of style. Why?
It’s because they’re practical and fashionable. They’re comfortable, attractive, and easy. Who doesn’t love slip-on shoes? Depending on which pair you buy, they can be affordable, too.
What’s your favorite style of loafer? Let me know in the comment section below!