Following in Jenna’s footsteps, I was asked to create my own Hugh & Crye Styled collage and I really lucked out with School Night. A shirt that’s reminiscent of one of my favorite eras (hence the Eames lounge chair), it evokes a sense of street cool that you just don’t really see anymore. What I like about School Night is the small, point collar, and the shirt itself contains a faint turquoise pinstripe on a fine poplin cloth.

Basically, I put together this look as if I was trying to figure out what to wear myself. Jeans would work with School Night, but I would prefer a slim-cut khaki. I’m really digging these desert boots too. The bow tie , aviators and fedora were just nice additions that complete the 1960′s working man feeling I was going with. To add a little jolt of aspiration, I threw in this Rolex Daytona watch just for the hell of it. Basically, I was showing how important it was to match your leathers. In this case, the watch band and the duffel bag.

The Result? A combination of classic Americana that will have you wreaking of confidence.