There are very few shoes that can claim to have done it all. The best penny loafers for men are among them. Born as practical slip-ons for Norwegian fishermen, adopted by Ivy League students, embraced by Wall Street financiers and later repurposed by everyone from front-of-house staff to fashion designers, the penny loafer has spent the better part of a century quietly proving its versatility. It is one of the rare pieces of classic menswear that can move effortlessly between worlds. Worn with a navy suit, it looks polished and considered. Paired with faded jeans and an oversized T-shirt, it feels relaxed and unstudied. Few shoes can pull off both with equal conviction.
Part of the appeal lies in its simplicity. There are no laces to fuss over, no flashy logos, no technical innovations to distract from the design. Just a clean silhouette, a distinctive saddle strap and enough history to fill several wardrobes. Yet despite its heritage status, the penny loafer has never really felt old-fashioned. If anything, its recent resurgence among well-dressed men suggests the opposite. As fashion continues to swing away from oversized trainers and towards something a little more refined, the humble loafer suddenly feels more relevant than ever.
Whether you're buying your first pair or looking to add another to an already healthy rotation, this guide covers everything you need to know – from the history of the penny loafer and how it should fit, to the best brands making them today and the easiest ways to wear them.
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.
History of penny loafers
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 fisherman’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 and giving birth to its preppy reputation. 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. 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.
What to wear with penny loafers
Laid back
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.
Mid-century cool
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.
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.
Where to buy the penny loafers for men in 2026
Myrqvist
Swedish label Myrqvist has quietly become one of the best entry points into the world of quality footwear. Its loafers are made in Spain using traditional construction methods and premium European leathers, offering a level of craftsmanship that would typically command a much higher price. The styling sits in a sweet spot too – refined enough for tailoring but relaxed enough for casual clothes.
Velasca
Founded in Milan in 2013, Velasca was built around a simple idea: sell traditionally made Italian shoes directly to customers without the usual luxury mark-ups. The result is a collection of loafers that feel unmistakably Italian, with elegant proportions, soft leathers and a slightly sleeker silhouette than their Anglo-American counterparts. Ideal if you favour casual tailoring and a more continental approach to dressing.
KLEMAN
French footwear specialist Kleman approaches the penny loafer from a slightly different angle. Known for producing hard-wearing shoes for public sector workers and government contracts, the brand's loafers have a distinctly utilitarian character. Chunkier soles and robust construction give them a modern feel that works especially well with workwear, wide-leg trousers and contemporary tailoring.
G.H. Bass
If there is a single brand synonymous with the penny loafer, it's G.H. Bass. The American shoemaker introduced the iconic Weejuns in the 1930s, helping establish the template that countless brands still follow today. With their classic proportions and rich heritage, G.H. Bass loafers remain one of the most authentic ways to tap into the shoe's Ivy League roots.
Gucci
No discussion of loafers is complete without Gucci. The Italian luxury house transformed the category in the 1950s when it introduced its horsebit loafer, a design that would become one of the most influential shoes in fashion history. Even today, Gucci loafers strike a unique balance between heritage, luxury and fashion credibility, making them a favourite among everyone from bankers to creative directors.
Alden
For many menswear enthusiasts, Alden represents the gold standard. Made in Massachusetts and famous for its exceptional shell cordovan leather, the brand produces loafers that are built to last decades rather than seasons. The styling leans traditional, but that's part of the appeal. These are investment pieces that improve with age and develop a character all their own.
TOD's
If comfort is high on your priority list, few brands do loafers better than TOD'S. The Italian label built its reputation on supple leather driving shoes, and that same emphasis on comfort carries through its penny loafers. Soft, lightweight and impeccably finished, they embody the sort of effortless sophistication that Italian brands do so well.
Crockett & Jones
Few shoemakers can match Crockett & Jones when it comes to balancing tradition and wearability. Made in Northampton using time-honoured techniques, the brand's loafers offer the sort of quality and longevity that justify their premium price tag. The designs are classic without feeling stuffy, making them an easy recommendation for anyone seeking a versatile pair that will work for years.
Dr. Marten's
Dr. Martens has given the penny loafer a distinctly rebellious edge. Its loafers retain the recognisable silhouette but add chunky soles, yellow stitching and a healthy dose of attitude. They're less country club, more Camden pub, which makes them a great option for anyone who finds traditional loafers a little too polished.
Grenson
One of Britain's oldest shoemakers, Grenson has spent the last decade successfully modernising its heritage credentials. The brand's loafers combine traditional craftsmanship and techniques such as Goodyear welting with contemporary detailing, often incorporating chunkier soles and slightly more relaxed proportions. The result is a collection that feels equally at home with tailoring, denim or military-inspired workwear.
Looking for more footwear inspiration? Check out our ultimate guide to smart winter shoes.
