They may have been around for the best part of a century, but penny loafers 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?

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


  1. Black Easy Weejuns Larson Penny Loafers
    £100
  2. Wine Easy Weejuns Larson Penny Loafers
    £100
  3. Mid Brown Easy Weejuns Larson Penny Loafers
    £100
  4. Wine Leather Logan II Weejuns Penny Loafers
    £140

History of penny loafers

G.H. Bass is heavily linked to the penny loafer - 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 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 high-waisted 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 long-sleeve polo shirt

Office ready

Penny loafers 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. 

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Looking for more shoe inspiration? Check out our ultimate guide to men's shoes.