The Best Penny Loafers for Men To Dress Up Any Look
Consider this lineup your ticket to loafer legend status.
The penny loafer is a bona fide classic—a shoe that’s stood the test of time. For decades, it’s been the go-to shoe for men who value style and versatility, working just as well with a suit as it does with a casual weekend look. But here’s the twist: while its roots are undeniably traditional, today’s takes on the loafer are anything but predictable. Designers are giving this timeless staple a fresh update, balancing the old-school charm with modern edge and a little bit of fun.
Whether it’s sleek and understated or bold and playful, there’s a penny loafer out there to match your vibe. From Ferragamo’s polished craftsmanship to Tom Ford’s contemporary take, brands are proving this classic shoe has range. Looking to keep it timeless or ready to take a style risk? Either way, the penny loafer is here to anchor your wardrobe—and maybe steal the show while it’s at it.
Ferragamo takes the penny loafer back to its roots while keeping it grounded in the now. Made from ultra-soft Italian calfskin, it’s the kind of shoe that feels as good as it looks. The double-stitched penny strap and chunky rubber sole add just enough edge to keep things casual without losing the classic appeal.
Ferragamo Penny Loafer, Trunc
Some shoes are bought; John Lobb’s Lopez loafers are built. Crafted to outlast trends and seasons, these leather classics balance durability with undeniable elegance. Smooth linings mean you’re not trading comfort for longevity, and their versatility makes them a go-to for everything from sharp tailoring to casual staples.
John Lobb Lopez Leather Penny Loafers, Mr Porter
A loafer with the right balance of classic and contemporary, this pair from Tom Ford is all about elevating the everyday. Made from full-grain leather, it channels timeless sophistication with penny slots and almond toes, but the branded buckles across the vamps bring a fresh, modern twist.
Tom Ford Sean Buckled Full-Grain Leather Penny Loafers, Mr Porter
A white penny loafer that’s anything but basic, this Saint Laurent pair is perfect for summer. With a sleek leather sole and subtle logo detailing, it’s a cool, clean look that pairs effortlessly with everything from shorts to tailored trousers. The embossed back tab adds a touch of luxury without going overboard.
Saint Laurent Le Loafer Penny Slippers, Zalora
These loafers are all about versatility with a twist. Made from army-green suede, they’re the perfect neutral to pair with almost anything. The classic penny strap adds timeless appeal, while the collapsible leather heels let you switch to relaxed mode when you feel like it.
Manolo Blahnik Plymouth Collapsible-Heel Suede and Leather Penny Loafers, Mr Porter
A penny loafer with a little extra personality, the Wilde from Duke + Dexter features a hand-drawn rose digitally printed on the vamp for a unique touch. It’s a fun twist on a classic, adding just the right amount of flair. Perfect for those who want to stand out, these loafers bring a bit of character to your shoe game while still keeping things sleek and stylish.
Duke + Dexter Wilde Red Rose Penny Loafer, Duke + Dexter
These Loewe loafers are anything but ordinary. Made from washed denim, they bring a playful twist to the classic loafer with a chunky, asymmetrical shape that stands out from the crowd. The hand stitching adds an artisan touch, but it’s the bold silhouette that makes these a statement piece. Fun, unexpected, and ready to add some character to your look, this pair proves that penny loafers can have a little edge.
Loewe Campo Loafer, Loewe
