John Varvatos USA LUXE Double Pocket Sport Shirt - Slim Fit

This design is all about playful color and vintage inspiration. Plus, Cole Haan uses Nike Air technology to maximize support and cushioning so it's exceptionally comfortable, too.

While the pen may be mightier than the sword, they both need protective sheaths. Store yours in this superior calfskin pouch from Montblanc, designed with a platinum-plated ring emblem on the exterior for signature style.

Paired stripes run parallel for a classically inspired dress shirt from Armani Collezioni, dapper with or without a tie.

Don't forget your favorite new hoodie when you're headed out for the night. A stylish top layer makes all the difference.