How to style a penny loafers

smart casual

Penny loafers (tan) + khaki chinos + white Oxford + navy blazer (sockless)

summer

Penny loafers (burgundy) + navy chinos + polo shirt (white) + sockless

smart casual

Penny loafers (dark brown) + grey trousers + light blue Oxford + field watch

Do

• ✓Wear sockless with chinos in summer — bare ankle against the saddle strap is the look
• ✓Choose tan, burgundy, or dark brown — all three work; black loafers are a different, more formal shoe
• ✓Pair with slim chinos that end just above the ankle to show the full loafer silhouette
• ✓Use invisible-sock liners if you must wear socks — they preserve the sockless look
• ✓Resole every 18–24 months to keep the leather sole from wearing through to the upper

Don't

• ✗Don't pair with athletic socks — the combination is the specific visual shorthand for dressing badly
• ✗Don't wear with shorts above the knee — the loafer needs enough leg below to balance proportionally
• ✗Don't combine with a chunky belt — the loafer's refined silhouette needs a slim, understated belt
• ✗Don't wear in heavy rain if they're suede — suede loafers water-stain permanently
• ✗Don't pick a loafer with a thick sole stack — the slip-on silhouette demands a slim sole

G.H. Bass

Weejun Larson penny loafer in tan leather

$100–150

Crockett & Jones

Cavendish penny loafer in dark tan

$550–700

Edward Green

Piccadilly loafer in antique brown calf

$1,400–1,800

Ownership dos

• ✓Wear sockless in summer with chinos
• ✓Choose tan, burgundy, or dark brown
• ✓Resole every 18–24 months

Ownership don'ts

• ✗Pair with athletic socks
• ✗Combine with a chunky belt
• ✗Wear in heavy rain (suede especially)