They may have been around for the best part of a century, but penny loafers for men are more relevant today than they’ve ever been.
If you’re after a classic, versatile shoe that’s just smart enough, then look no further.
Penny loafers are an easy-to-wear style that can be worn for a wide range of social occasions and dress codes and are well worth a spot in your shoe rotation.
But what exactly are they and how should you wear them? Scroll on for our ultimate guide to men’s penny loafers, including our pick of the best pairs out there.
What Are Penny Loafers
A slip-on style shoe, penny loafers are defined by a small detail located on the vamp.
Across it on the top of the shoe, you’ll find an additional stylised piece of leather with a small cut-out, which gives the shoe its name.
In the ’40s and ’50s American college students took to the style, putting pennies in the cut-out, partly as a way to stand out, but mostly so they had change to pay for phone calls home. Penny loafers were born.
A simple style, they’re often slim in profile and as a result, don’t look out of place worn with tailoring.
A laceless design ensures pennies don’t stray too far into formal territory though, meaning they combine well with denim and workwear.
The Origin
G.H. Bass is heavily linked to penny loafers for men – the US brand popularised the style when it brought it to America back in 1936.
The design was inspired by traditional Norwegian fishermen’s shoes and, as a nod to this, G.H. Bass called its version the ‘Weejun’ to pay homage to its origins.
Initially, the American market favoured their Weejuns as house slippers, but it didn’t take long for them to be worn out and about.
It was those penny-wearing Ivy League college students who helped make the style a casual menswear staple, adopting it as their de facto uniform, becoming associated with the Preppy life and the Preppy style.
American college students continued to rock penny loafers on campus throughout the ’50s and ’60s and were further bolstered by prep-king John F. Kennedy, who too enjoyed them throughout his (most stylish) presidency.
Penny loafers were also enjoyed by everyone from James Dean and Paul Newman to sub-cultures like the mods and rude boys to Michael Jackson, who wore his Weejuns while moonwalking.
A cornerstone element of the Old Money style, today, penny loafers for men maintain an air of preppiness but can be incorporated into a range of looks. Versatile and effortless, they’ll finish off tailoring or a layered weekend look with ease.
Modern Penny Loafers
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 swap out the pennies in favour of some playful tassels.
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 capsule wardrobe – wear it instead of sneakers with jeans or chinos, or instead of dress shoes with summer-weight suits.
And of course, swap out the boat shoes to wear a penny loafer with shorts for a truly stylish old-money summer look.
Don’t be precious with your loafers – just wear them like you know how good you look (because I know you do).
What to Wear with Penny Loafers
Now, apart from its penny-holding feature, if you are wondering how to style penny loafers, worry not.
In this section, we will learn about the different ways to wear penny loafers for men to look stylish and modern:
With Dress Pants
One of the most common choices when buying a pair of penny loafers is brown loafers.
Brown penny loafers go well with almost anything.
Want to wear it with casual outfits? Go ahead. Want to wear it with business outfits? Go ahead with it too. Date night? No problem.
Of course, you cannot wear the loafer with the same material for all occasions.
Leather brown loafers would be perfect for more formal events like business dinners and meetings.
Match it with a formal outfit(especially with blue formal pants), and you are good to go.
With Suits
The black leather penny loafers are a really good choice for formal or semi-formal outfits and occasions like date night with your girlfriend and even wedding events where you tend to wear jeans a lot.
They also tend to blend well with semi-formal outfits like white cotton pants and could be styled with blazers.
You can choose to style black leather penny loafers with a white dress shirt and black suit to look brilliant on both semi-formal and formal occasions.
With Chinos
With the obvious two choices out of the way(brown colour and black colour), there are certain outfits that are better with colours other than black or brown, like the white loafers.
They are a great choice if either your shirt or pants are white.
Now listen, black looks good too with the previously mentioned outfit.
But white loafers make the same outfit even better.
Unlike the black and brown ones, white loafers are not really meant for formal wear.
They are more casual outfit-oriented, but hey you can always go for white loafers and formals if that’s what you prefer.
With Jeans
“How to wear penny loafers for men” is never complete without mentioning classic black loafers with jeans.
If you ever feel confused about which colour to pick as your first, go for black.
They are a perfect choice for formal wear. If you ever plan on wearing dark colour bottoms, wearing black penny loafers is the choice I would suggest.
Just wear a plain white shirt with blue jeans and you are ready to live out the day.
Be it dark cotton pants or jeans, for formal or informal occasions, a black loafer can never disappoint you.
They are great for casual day-to-day wear too.
With Shorts
When it comes to knowing how to wear penny loafers for men with style, just remember this: the majority of the loafers are either made of leather material or suede material.
Penny loafers are also perfect to be paired with shorts to feel relaxed and stay comfortable all day.
They instantly make you look smarter and formally ready.
On the other hand, penny loafers are the perfect choice for more casual or informal outings like dinner dates, everyday wear, movies, casual dinners, and so on.
These make you look stylish and smart, while at the same time giving you that informal, casual look.
Styling Penny Loafers by Occasion
Semi-formal
Can you wear loafers with a suit? Of course! Just keep the proportions slim, so the effect is “smooth sophistication” not sloppy.
Go sockless (or no-show socks) for a debonair, laid-back vibe.
Business Casual
Roll up your sleeves (here’s a primer if you need it) and get to work, in this office-appropriate look.
Stick to no-show socks in the warm weather months for a little dress code-friendly ankle-flashing.
Smart Casual
Roll your chinos and pass the guac.
This look is cool and casual, and could easily be worn with sneakers; which is exactly why penny loafers make for a fun and unexpected statement.
Outfit Ideas With Penny Loafers
Ivy League
Hark back to the penny loafer’s mid-century Ivy League heyday and opt for a pair of belted wide-leg trousers.
Make sure to have the hems tailored or simply roll them up to allow some of your socks to show underneath, and complete the look with a knitted polo shirt.
Classic Off-duty
Slim dark denim never fails to look cool when worn with penny loafers.
Go for raw denim or black jeans and pair them with a similarly dark T-shirt for a classic off-duty look.
Office Ready
Penny loafers for men are more than appropriate for a smart office look.
A G.H. Bass oxblood pair adds a point of difference and will jazz up an otherwise minimally-styled outfit consisting of slim trousers and a plain white shirt.
A classic Mac coat completes the look, harking back to the mods of the 1960s.