• Fashion
• shoes

By Anna Maria Giano

The penny loafer has always loved a good story. In the 1950s, American college students slipped a coin into the leather strap of their loafers, reportedly to cover an emergency phone call. The nickname stuck, and the shoe became a symbol of easy, preppy elegance.

A few years later, Audrey Hepburn gave it pure poetry in Funny Face. Wearing a black turtleneck, she dances through a smoky Paris café in loafers and white socks. Her moves turned a schoolboy staple into an icon of bohemian chic.

UGG has its own sunny legend. In 1978, an Australian surfer brought sheepskin boots to the beaches of California, and the cozy shape gradually conquered the world.

Anderson personally chose the colors, and the orange version feels like a sweet wink to Hynes and his musical alter ego. To channel Hepburn, pair your loafers with cropped black trousers and bright white socks. The chestnut loafer boot looks lovely with a pleated midi skirt and a chunky cardigan.

On weekends, khaki suits wide-leg corduroys and a crisp striped shirt.

For the office, try the orange style with a soft gray suit for a sunny jolt of color.