Editor's note: Welcome to the first installment of "Fly or Fail," a regular column in which our fashion expert, Samantha Rubin, will rate athlete style off the field.

The intersection of sports and style reached a crescendo last summer during the NBA playoffs, with all kinds of buzz on the fashion choices of Rondo, LeBron Westbrook, D-Wade...and, uh, Rondo. Although athletes have always been in the spotlight, never before have we seen so many jocks embrace the role of trendsetter and style icon. And we're not just talking about the superstars -- even lesser-known guys are pushing the fashion envelope, for better or worse.

Which begs the question: How well do they hold up under the fashion spotlight? For the first edition of "Fly or Fail," we're taking a look at the athletes who've quickly become the men about town during New York Fashion Week. As you'll see below, some were dressed to impress and some were ... not.

Athlete: Tyson Chandler, Knicks
Event: Alexander Wang show, Sept. 8

Outfit: Since Tyson Chandler came to NYC from Dallas, he quickly has become one of the big city’s best-dressed athletes, giving teammate Amar’e Stoudemire a run for his money. His tailoring is always on-point, usually in custom Waraire Boswell suits and Esquivel shoes, and has a clear understanding of how to dress his 7-foot frame. But I start to question my judgment after seeing Tyson heading to shows over the weekend. I can’t knock him for trying to push the envelope and having the confidence to do so, but the leather shorts just look like pants that he borrowed from his stylish wife, Kimberly. Men should not wear tunics. Ever. I dig the oxblood Esquivel boots, but not with a capri pant — they would look great under trousers, a pair of jeans or even longer leather pants! NYC Fashion Week, like the NBA, is full of peacocking — who can outdo whom and who can be photographed the most — but Tyson should know this will not land him on any best-dressed lists!

Verdict: Peacocking FAIL!
Athlete: Brad Richards & Carl Hagelin, Rangers
Event: Joseph Abboud Spring 2013 fashion show, Sept. 5

Outfit: Hey, King Henrik isn't the only guy who can dress on the Rangers! Both Richards and Hagelin are wearing Joseph Abboud here in support of the designer's show. While a bit conservative, the takeaway here is you cannot go wrong when your suit is tailored to fit your body. I'm a fan of the two-button suit, which is the modern and age-appropriate choice for Brad and Carl (ages 32 and 24, respectively). They kick up their style game by also rocking peak lapels, which is a bold style statement when compared to a subdued, classic notch lapel. These two details take them out of the boardroom and straight to the front row. Brad's white pocket square is a good way to balance out a tailored look when not wearing a tie, adding some depth to a rather simple look.

Verdict: Road to Stanley Cup FLY.
Athlete: Dwyane Wade, Heat
Event: Calvin Klein Collection Celebrates Fashion's Night Out 2012, Calvin Klein Boutique, Sept. 6

Outfit: Fully outfitted in Calvin Klein for his FNO appearance at the Calvin Klein store, D-Wade proves he can pull off a look I’d like to call "Modern-Day Miami Vice." Again proving the importance of tailoring and fit, Wade sprinkles in some NBA championship confidence for a winning combination. Some people think that sneakers with a suit is unacceptable, but Dwyane pulls off the footwear choice for a few reasons: One, he's chosen a simple black T-shirt instead of a stuffier dress shirt to create a casual look; and two, the sneakers are not his game-day Jordans. Metallic is an edgier choice but they read as neutral and blend into the rest of his look without being overpowering. He tops it off by keeping his accessories low-key with a simple chain and a sleek Hublot watch.

Verdict: Championship FLY.
Athlete: Russell Westbrook, Thunder, and Rajon Rondo, Celtics
Event: GQ & Nordstrom Launch Pop-Up Store On Fashion's Night Out at Nordstrom's Treasure & Bond Store, Sept. 6

Outfit: I’ll go on record and say I’ve given these guys a style smackdown in the past, but their individual style has been growing on me a bit. Westbrook is clearly holding on to his bold shirt choices and really went for it by choosing leopard this time around. What he does well here is pairing a shirt that fits perfectly with a neutral green pant that tones down the top's louder effect. Russy is having fun with fashion, and isn’t that what it’s all about? Can’t knock him for that! (Meanwhile, Rondo definitely gets style points for ditching the referee look he wore during the playoffs for a more modern, monochromatic look. The problem is that the tuxedo jacket still looks a bit too formal and oversized, paired with black jeans and denim shirt. Both guys chose Christian Louboutin studded sneakers, but Rondo’s outfit would benefit from Westbrook’s choice of solid black.

Verdict: Westbrook: Individuality FLY; Rondo: Upgraded FAIL
Athlete: Ryan Lochte, U.S. Olympic gold-medal swimmer

Event: "Guys Fashions Night Out" Presented By Ainsworth Park and Windsor Custom, Sept. 6

Outfit: Ryan Lochte? Um, sartorial genius he is not. When being dressed by Ralph Lauren he looks on-point, but when left to his own devices, he ends up on the red carpet looking like he's hitting up a college bar in Gainesville. I do give him points for not accessorizing with his now-famous grill and happy to see the proper fit of his T-shirt and jeans, but I think he needs to leave his styling to the pros. Lastly, I'd lose the necklace, which is a bit dainty and seems forced and outdated.

Verdict: #JEAH! FAIL