I hear it from guys like you all the time. You want to expand your footwear repertoire, but keep falling back on old standbys.
Of course, here at SG HQ we love a man in a chukka boot or white sneaker, but it’s good to switch it up from time to time, too!
Enter: penny loafers.
Penny loafers strike that retro-yet-timeless vibe that looks so good on guys.
Plus, these shoes are quite literally effortless (slip on! no laces!), and you can dress them up or down. Really, there isn’t any good reason not to add a pair of penny loafers to your shoe collection.
Below, learn why Team SG loves a man in a loafer, and see how to wear penny loafers in more outfits.
In this guide to men’s penny loafers, you’ll discover:
- What is a penny loafer?
- Are penny loafers in style?
- What to wear with penny loafers
- Shop the best penny loafers to buy for men
What is a penny loafer, anyway?
Relatives of the penny loafer include plain loafers (usually made of leather), tuxedo loafers (perfect for black tie events), Italian loafers which have a metal strap across the top, and driving moccasins a more casual shoe, worn at home or driving a sports car in some European country.
The penny iteration came to be in the 1930s. John Bass—of G.H. Bass…maybe you’ve heard of ’em?—decided to add a stylish strap to the basic loafer, creating a new look that he called “Weejuns.”
Why are they called penny loafers?
The Weejuns’ strap had a design looking like a pair of lips, and people would dress up their shoes by putting small items – like pennies – in the strap.
Some would even use the penny at a pay phone for emergency phone calls home.
(Note for Gen Z: Pay phones are what millennials used to let their parents know they were ready to be picked up at the mall)
Are penny loafers in style?
Short answer? Yes! Longer answer? Ye-e-e-e-e-e-s-s-s-s.
This isn’t your dad’s penny loafer… Okay, actually, it is, but it’s time you stopped thinking of it like that.
Given the penny loafer’s ability to look even more stylish sans socks, and also its throwback vibes, it’s time to get onboard with this footwear for the future.
Right now, there’s also a thicker, lug sole style that gives a new spin to a timeless shoe.
This is more trendy, so feel free to go with the more classic style if that’s more “you.”
You can always mix it up with penny loafers that come in suede, or add some playful tassels.
Why penny loafers deserve a place in your wardrobe
While the penny won’t get you very far these days, the style has stood the test of time – and for good reason.
The shoe is a great addition to your wardrobe – wear it instead of sneakers with jeans or chinos, or instead of a dress shoe with summer-weight suits.
And of course, swap out the boat shoes to wear a penny loafer with shorts for a truly stylish summer look.
Don’t be precious with your loafers – just wear them like you know how good you look (because I know you do).
Below, check out what to wear with penny loafers:
From work to play, you’ll find this throwback shoe is ready for anything your wardrobe can throw at it.
MONDAY
How to wear penny loafers to a job interview
SG Says: Can you wear loafers to a job interview? Of course! Just keep the proportions slim, so the effect is “smooth sophistication” not sloppy.
Visible white socks are very in right now, but you could also opt for no-shows.
Maybe skip the beanie, but hey, you do you!
TUESDAY
How to wear penny loafers in a casual outfit
SG Says: Roll your jeans and pass the guac. Both these looks are cool and casual, and could easily be worn with sneakers…which is exactly why penny loafers make for a fun and unexpected statement.
WEDNESDAY
A penny loafers outfit for the office
SG Says: Every guy can pull off this preppy-inspired, office-appropriate look.
Toss a sweater around your shoulders for an extra bit of ivy style.
THURSDAY
How to wear loafers with jeans
SG Says: Jeans and a chambray shirt? All day.
The straight-fit of the jean ends right at the ankle for a look that’s casual without being sloppy.
FRIDAY
A penny loafers outfit idea for a date
SG Says: This loafers outfit would be great on a date, for a vacation, or any off-duty occasion where you want to look effortlessly debonair.
Below, shop the most stylish men’s penny loafers
Looking for an off-duty pair of penny loafers? Start with brown leather and a more casual sole.
Classic leather penny loafers, one in black and one in brown.
Dan lug leather loafers, $250
two-tone penny loafer in milkshake, $704
Looking to invest in a more trendy pair? Go for a lug sole or two-tone suede.
More men’s footwear style stories from SG HQ
Wear Your Loafers with Shorts (Really)
