Winning isn’t just about hitting a jumper in the fourth or perfecting your end-zone dance. Your ability to constantly evolve, push yourself and inspire greatness in others all give you an edge. Just like you, these style staples were redefined for the season. Try them on for size (and if a bit too pricey, simply use the looks for inspiration). — Ericka N. Goodman

1. Above the Fray

The thick-soled creepers of the past may have freaked you out. But thanks to the good people at Salvatore Ferragamo, the silhouette has been upgraded by adding an athletic-inspired grip to the sole, an embossed upper and leather lace covers. The high-fashion-meets-function mashup will allow you to creep confidently all over town. And, don’t forget your briefcase. Normally seen in shades of black, gray or metal, this two-tone carryall is neutral enough to bring into the boardroom, and its unique color combo stands out in the crowd.

Salvatore Ferragamo Creeper  Sneakers ($1,200; 866-337-7242) and Burberry Barrow Bag ($2,395;

2. The Exception to the Rule

Wearing a motorcycle jacket with a T-shirt or a tuxedo can give you an instant air of rebellion; it’s a universally transformative piece. This find in particular—with its smooth metal hardware, gray hue and pinstriped interior—is just so special. The perfect combination of free-spirited style and luxury, the classic has become a bit more refined.

John Varvatos Laser Cut Biker Jacket ($2,998;

3. A Timepiece for Titans

Literally the Bentley of watches, this chronograph was designed as an extension of the luxury carmaker’s aesthetic. The watch features a knurled motif bezel, a nod to the automaker’s radiator grill, and an exclusive variable tachymeter, which calculates average speed and distance during a denoted time span. Beyond just looking the part, this arm candy is a world-class piece of technology.

Breitling for Bentley B06 Watch ($12,370;