best penny loafers gentlemans journal

These are the best penny loafers money can buy

From a pair of effortlessly elegant Italian slip-ons to classic British penny loafers, these are the best to buy...

Penny for your thoughts on loafers? Because they really, really split opinion. Unlike boots, brogues and a whole stampede of other shoe designs, people either wear loafers all-year-round — or they’ve never touched a pair in their lives. We don’t know what it is, but no other form of footwear is as divisive as the simple, slip-on loafer.

But it needn’t be that way. Once you dabble in the world of low, lace-less shoes, you’ll never look back. From versatility to practicality, they’re an enduring design for a reason. In fact, the first ever loafer was developed for the landed gentry and the royal family in 1847. But it’s a different design we’re interested in.

Namely, the penny loafer. Developed by G.H. Bass in 1936, the penny loafer features a leather ‘saddle’ strap across its upper — complete with decorative cut-out. This cut-out made the style very popular with American prep school students, who would store pennies in the saddle slot for making pay phone calls — hence the name. Today, it may be a quirk we no longer need, but a pair of penny loafers remain a quality investment. Here are some of the best…

For European elegance, Tod’s Loafers in Blue Suede

Before we delve into the world of quality British shoemaking, let’s flit across to continental Europe for a lesson in understated style. Although you can buy your penny loafers buffed to a burnished high-shine, there are few options more chic than suede. From Tod’s, these dark blue slip-ons are stamped with the brand’s monogram and feature a rubber outsole with embossed rubber pebbles.

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Tod’s Loafers in Blue Suede


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For a suit-appropriate option, Church’s Drayford Loafers

A classic, conservative option. From Church’s, this ‘Drayford’ design is as traditional as it is reliable. With a hand-stitched apron, lightweight leather sole and internal lining for comfort, these loafers are built to last. And, with slick, black vintage calf leather uppers, they’re the sort of slip-ons you can wear with a suit.

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Church’s Drayford Vintage Leather Loafers


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For a shoe of true beauty, Cheaney's Saxon Saddle Loafer

Church’s loafer above may be practical, but Cheaney’s is beautiful. Just look at those magnificent uppers; crafted from the finest calf leather and finished with a bronzed espresso sheen. Peer in at the design’s distinctive navy leather lining — or flip the loafers over to admire the in-channel stitched oak bark leather soles. With a sophisticated shape and undeniable elegance, these are perhaps the suavest shoes on this list.

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Cheaney Saxon Saddle Loafer


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For flexibility and versatility, Edward Green’s Piccadilly Loafers

Versatile in both shape, style and texture, Edward Green’s take on the penny loafer is perfect for weekdays and weekends alike. The soft almond toe and distinctive apron are neither too sharply-cut or too soft; the natural texture suits both tailoring and more casual attire; and the leather soles are strong enough to take on any terrain.

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Edward Green Piccadilly Loafers


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For casual suiting, Scarosso’s Stefano Moro

Back to Italy for a second. The Stefano Moro penny loafer from Scarosso takes a hard-wearing approach to craftsmanship that rivals even Northampton shoemakers — and stitches it tightly together with continental levels of cool. One of our summer suiting staples, these Stefano Moro shoes are elegant, simple and finished with a beguiling brushed-up texture.

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Scarosso Stefano Moro


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For classic car shoes, Crockett & Jones’ Cadogan Loafers

There isn’t an official uniform for classic car drivers — but these tobacco suede loafers from Crockett & Jones would surely make the cut if there was. The ‘Cadogan’ designs from the British shoemaking icons are crafted from the finest tan calf suede and finished with single leather soles — perfect for pushing down the pedals on your Triumph GT6…

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Crockett & Jones Cadogan Tobacco Suede Loafers


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More of a brogue man? Here are the best money can buy…

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