Dress for the Job You Want:
Pilot for Hire: Military Shirt

The shirt: Back when we were mere commercial or military pilots, the epaulets on our uniforms held our rank and status. Now, the lack of any shoulder adornments on our shirts is every bit as telling. The breast pockets are always useful for holding cigarettes or, if we believed in paperwork (which we obviously don’t), our notebooks, flight plans, cargo manifests, and other crap that lesser pilots might find necessary. Ralph Lauren Rugby (1 – $80), Shades of Greige (2 – $74), and “Vintage” BDU by Rothco (3 – $32)

Easy Style Points: Sunglasses

The point here is simply not looking like a professional bass fisherman, NASCAR driver, or an avid fan of either sport. Sporty glasses are best left to the beach volleyball court, speed skating rink, or baseball diamond, but there are still tons of great options for every-day, around-town shades.

Designer Spotlight: Benjamin Bixby

But with a nod to pockets of mid-century dandiness, Benjamin Bixby by Andre Benjamin offers some classic pieces and great conversation starters. We’re huge fans of vintage styling here, so a label that takes its style cues from days gone by is ok in our book. This is straight-up legit Man Style, but it’s the attention to detail – fabrics, construction, and adornments – that gives Benjamin Bixby the chops to transcend gimmicky vintage status.

The debut line (above) paid homage to the natty-dressed world of college football in the 1930s. The F/W 2009 collection, which can be previewed at The Fader, looks instead to the world of the roguish WWII fighter pilot. Finally, there is celebrity-inspired style men can feel good about. Read more about Andre Benjamin’s personal style and take on design at The Guardian.

Easy Style Points: Casual Shoes

The problem with 99% of running shoes is that they are so blinged out with technology and space foam and glo-sticks and nano-fibers that they might as well be from the future. As timeless looks tend to be a little more stylish, shoes from 2016 don’t quite fit the bill. A good rule of thumb, I think, is that if you could actually use a shoe for some kind of athletic training or competition, it is probably best left to the track or gym. Instead, try one of the following upgrades: