The Definitive Rules of Flip-Flop Etiquette

Two summers after the Northwestern women’s lacrosse team made national news by flip-flopping through the White House, many of us still won’t admit that sometimes the thong is all wrong. Sure, they’re comfortable, and high-end designers are peddling them for $600. But if you want to go bare, you’ve got to play by the rules. Our opinionated panel—all of whom have seen plenty of flip-flop faux pas—outlines how to wear the style gracefully.

1. Heed the forecast.
Philip Surette, public relations representative, Neiman Marcus: “It’s all contingent on the weather. It must be warm out. Wait till the season’s right—no sooner than June. Otherwise, I absolutely cringe.”

James Sun, manager, Oishii Boston: “Appropriateness solely depends on the environment. If someone comes in wearing flip-flops, we offer them outside seating. It’s comfortable and casual. It fits.”

2. Get a pedicure (that includes you, too, mister).
Cameron Shirvani, manager, Jimmy Choo: “The loud sound of a flip-flop clack draws lots of attention to your feet, so people immediately notice if your heels are dirty and your toes aren’t manicured.”

Philip Surette: “I don’t care who you are—woman, man, whatever. It’s been a long winter. Go ahead and get it done.”

3. Just say no to rubber.
Harley Bilzerian, buyer, Alan Bilzerian: “Rubber is only for the beach, walking over rocks or something. Wait, I take that back. You can also wear them when you’re washing your car.”

Gretchen Monahan, owner, GrettaLuxe: “Invest in a pair in a more lush material—snakeskin or something with jewels. It’s a very beach-chic look, so make sure the rest of your look is casual yet elegant—all tied together.”

4. Know when to skip them altogether.
Jo Cardin, media manager, Boston Ballet: “Take pride in the theater experience. It’s a chance to get dressed up and buy a new pair of shoes.”

Gretchen Monahan: “You shouldn’t be showing that much foot at the office. Peep-toes or mandals are much safer bets for casual Friday.”

Harley Bilzerian: “Never wear flip-flops on a date. You need something classier.”