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I love rocking a pair of cool sneakers. But sometimes, they just aren’t appropriate for the occasion. When can I stretch the rules to sneak in a cool pair of my favorite tennis shoes?

I love rocking a pair of cool sneakers. But sometimes, they just aren’t appropriate for the occasion. When can I stretch the rules to sneak in a cool pair of my favorite tennis shoes?

If you’re looking for stylish role models, everyone from Run-DMC to Justin Timberlake has stepped out of traditional fashion guidelines to prove that swapping shoes for sneakers can be acceptable and make you look pretty cool. The question is not whether you can pull off the “I don’t play by your rules,” look, but how to do so when you’re off the court and on the town.

A cool pair of sneaks can play in almost any environment, as long as they’re paired with the right threads. Obviously, jeans are the go-to matchup, but only if they’re blue jeans. Combine a pair of white sneaks with black jeans, and you’ll look like you wandered off the grounds of a convalescent home.

Here are a few of my favorite kicks that can make the jump from the health club to the nightclub -- and other destinations -- without making you look like a minor-league style guy.

Canvas Cool
A pair of Converse Chuck Taylors ($46) has become an iconic hipster statement. Pair them with jeans and an open-collared shirt over a solid tee for an all-star combination, or contrast them with a solid-colored pair of dress pants for a bolder statement. Either way, if they’re fresh and clean, they say that you’re willing to take a risk -- not that you didn’t have a chance to change on your way home from practice. Just note that these sporty statements are better suited for trendy parties, gallery showings and clubs than an uptight dinner with the in-laws.
Superstar Style
Adidas Superstars ($50) hit the ground running way back in 1969 and became the signature shoe of UCLA’s record-breaking college basketball dynasty in the ’70s, when they became the world’s largest accessories on the feet of Kareem Abdul Jabbar. They were reborn in the ’80s when Run-DMC rapped “My Adidas” into another record-breaking milieu. These days, the classic leather, three-striped style is making another run into the fashion arena, showing up on the feet of such Hollywood all-stars like Brad Pitt and Robert Downey Jr. They’re now available in many more colors and lend sporty style to any outfit, whether you’re hitting the clubs or the backboards.
High Style
High-tops are up on the top of the stylish list again, and these days there are more individual styles to choose from. You can kick ass in any crowd with a pair of high-top, boxing-inspired shoes that have been seen on the feet of the rough and famous, from Mickey Rourke to Sly Stallone. The Adidas Box Hog Ring Shoes ($60) offer high-rise elegance with the classic three-stripe, black-and-white signature style that’s has scored a knockout this season with celebrities and wannabes in clubs across the country.
Cole Mine
Kenneth Cole is so smooth he makes sneakers that look like expensive shoes. You won’t lose a step, even with a formal crowd, with a pair of Resort Area ($138) men’s imported leather sneakers with lace-up closures and man-made leather sole. These shoes can sneak into any occasion -- without missing a beat. You can wear them with anything from dress slacks to a suit and bounce from the gym to the boardroom.
Glide in Clydes
Air Jordan wasn’t the first shoe named after a superstar. Say hello to our little friends: The Puma Clydes ($77), named after the super-fly style master of the ’70s, New York Knicks guard Walt “Clyde” Frazier. Sporting wide-brim hats and pinstripe suits, Frazier made his namesake’s never-before-seen suede sneaks his signature. No longer a staple on the court, Clyde’s kicks never lost their cool on the street, where they are perfectly acceptable with white linen pants for an evening beach party, or a blazer and a quality polo shirt for a summer dinner with a special lady who’ll find your style statement sexy.

About the Expert

Lana De Doncker is the lead stylist and chief photographer for Downtown Magazine NYC in Manhattan.

Tags: Style