Best Feet Forward: Men’s Shoe-Sock Combos for Every Occasion

If clothes make the man, then the right socks and shoes make him stylish.


And make no mistake: Combining the two can be tricky business. Done wrong, “they can easily ruin the entire look,” says Joe Lupo, co-founder and creative director at Visual Therapy, a styling firm based in New York. Done right, “they can easily make an outfit,” he says.

Black Tie

Men’s fashions are still pretty closely prescribed, and sock-shoe combinations offer the chance to be creative for nearly every occasion. One big one: The black-tie gala, which requires a tuxedo or, at the very least, a smart business suit in dark color. For these occasions, a patent tuxedo shoe and sock with a subtle pattern work well. “The rule, if we can make one, is to keep it a little more muted,” says Ryan Beshel, a Chicago fashion publicist who blogs about fashion at Beshel suggests a subtle pin-dot or striped sock with those shiny shoes: “Don’t put crazy camouflage with black tie,” he says.

Hugo Boss Mellio patent tux shoes, $225

Business Meeting

An important business meeting also calls for a little more restraint in the socks-and-shoes department. Beshel suggests a classic cap-toe oxford rather than the square-toe numbers popular several years ago. “They’re just not good for anything,” he says. A patterned sock that picks up the color of the shoe—no brown with black, please, and no white tube socks with anything—turns business attire from staid to stylish.

Dotted Happy Socks, $12

Night Out

For a night on the town, with Ms. Right or the guys, it’s perfectly acceptable to take advantage of the wild-sock trend. Colorfully patterned numbers by Stance, Happy Socks and Jonathan Adler fill the bill. For casual shoes, consider a sleek, anywhere-but-the-gym running shoe from Creative Recreation or ohw?. “People like the clean silhouette of the runner,” says Jon Cotay, co-founder of Akira, the Chicago-based chain of boutiques that has men’s stores in Bucktown and Andersonville. Even with suits, a sleek running shoe “is just cooler than a dress shoe,” he says.

Stance cotton “Cano” socks, $14

Creative Recreation Casso trainers, $95, Akira Men, 1910 W. North Ave., Chicago

Casual Cool

Another casual option, say for primo seats in a skybox at Soldier Field, is a rubber-soled ankle boot. Here-and-now boots combine leather and another fabric: wool or even canvas. “That’s a really interesting trend in men’s footwear,” Cotay says.

ohw? Gatland boot, $265, Akira Men, 1910 W. North Ave., Chicago

No matter the occasion, shoe-and-sock pairings should follow a few rules:

  • Invest in high-quality shoes, and when in doubt, “go with a classic,” Lupo says.
  • Don’t sacrifice comfort. With designers such as Tom Ford turning out stylish, rubber-soled footwear, there’s no need to.
  • Tread carefully with colors and patterns. “Make sure (shoe and sock) colors make sense with the colors you’re wearing on top,” Lupo says.

Pictured top right: Jonathan Adler Cross Plus socks, $14