Being named one of Esquire magazine’s Best Dressed Real Men in America is quite an honor. You are judged against thousands of other uniquely debonair denizens from around the country, each donning his best garb and vying for the coveted sartorial title. But the reality is you’ve got a better shot at nabbing a pair of Gucci horsebit loafers on clearance (hint: never going to happen) than you are to nab the distinction. Which makes the fact that best friends Ontario Armstrong and Clifton Wilson were each finalists (in 2009 and 2006, respectively), a well-appointed scoff in the face of the odds.

“We were invited to an Esquire event in New York, and we went up together… the editor had no idea that we were friends,” says Armstrong. “He kept saying, ‘How did we pick two best friends as Best Dressed? Both from Philly, both from the same school, how does this happen?’” Armstrong laughs, recalling the editor’s disbelief. “People were saying, ‘This has to be rigged.’”

But it wasn’t, and this decidedly dapper duo from Mt. Airy (Armstrong) and South Philly (Wilson) has the fashion chops to prove it.

After meeting 13 years ago as fashion design majors at the Art Institute and later working together at Nordstrom dressing Philly’s power brokers in suits and finery, the pair got the itch to break off on their own. “We both knew we wanted to have our own brand, but we didn’t know where to start,” says Wilson. “We had a lot of trial and error, and eventually found our niche through all of that.”

That niche? Sublimely sophisticated pocket squares. “Men were just getting back to adding details to their look,” says Armstrong about the impetus for honing in on the oft-forgotten accessory. “We thought, Let’s do something to complement that; let’s do something like pocket squares. But what can we do to separate us from everyone else? Let’s do something cool; let’s [give] each pocket square its own [persona].”

Almost three years and hundreds of well-accessorized men later, the pair’s eponymous Armstrong & Wilson line has become a lauded purveyor of these refined little accoutrements.

“They are for the young professional and that trendy older guy,” says Wilson about their clientele. “The squares are out of the box for that conservative guy who likes to combine classic with a modern twist, [for] that young professional who just got a good job and doesn’t mind taking a little risk. And then there’s that older gentleman who’s classy, but still wants to keep his look fresh.”

With a functioning hand-sewn button as their signature, the 65-plus different pocket square designs run the gamut from sophisticated and refined to wild and funky. And with Armstrong and Wilson each designing according to their own personal aesthetic, it is clear which squares can be attributed to which designer.

“It’s funny, our styles are so different even when it comes to pocket squares,” says Armstrong. “You can definitely tell what’s an Ontario square and what’s a Clif square. Clif is very classic and straightforward in his look. He loves [an] ultra-conservative square like The Tooth—gray and black houndstooth with a burgundy trim and wood button. Me, I’m a little more risqué and adventurous when it comes to what I put on. I am more The G.I.—camouflage with pink trim,” he laughs.

Since becoming darlings in the international fashion blogosphere, the brand now has its well-dressed devotees clamoring for a wider breadth of accessories. Armstrong and Wilson are more than happy to oblige. This fall marked the debut of a small collection of 12 ties; 18 new ties (think madras, chambray, and linen), along with countless new pocket squares, are on tap for spring 2013. Bow ties and suspenders are definitely on the horizon.

As for the man who may be intimidated by the thought of donning a dapper little square, Wilson implores all men to give it a shot. “My definition of a well-dressed man starts with confidence,” says Wilson. “No matter what you’re wearing, you have to show confidence when you’re wearing it. Style is in the beholder.” 

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