Duke + Dexter x Playboy Wilde Penny Loafer, $165
Black penny loafers are essential in every wardrobe, but this collab pair brings a cheeky detail: a literal, Playboy-branded coin tucked into each shoe.
Dr. Martens Adrian Tassel Loafer, $130
Dr. Martens boots hog most of the brand’s spotlight, but don’t sleep on the chunky (and tasseled) loafers made from its iconic leather.
Aimé Leon Dore Penny Loafer, $245
Hypebeast business casual, anyone? ALD’s loafers are a sleeper hit for their versatility between casual and dressed-up fits, especially in this deep forest hue.
H By Hudson Ipanema Woven Loafers, $134
These leather slippers could easily step from the beach to the city streets, with an espadrille shape and croc-like woven pattern.
Camper Walden Low-top Loafers, $180
If you already own black penny loafers, or if your wardrobe leans more anti-neutral, metallic pink pennies are a natural next step.
Steve Madden Aahron Leather Loafer, $120
Horsebit loafers are another timeless essential, but not everyone can hand over $1,000 for the Gucci originals. This sleek pair delivers the same timeless cool, for a tenth of the price tag.
Vinny’s Romeo Croc-effect Leather Penny Loafers, $180
This pair offers a trendier take on the classic penny, but the embossed crocodile is arguably just as versatile as solid leather.
Vagabond James Loafer, $210
This pair upgrades the classic penny shape with a lifted lug sole, tapping into the platform trend without sacrificing versatility.