This collaboration between Book Works and adidas pulls inspiration from jazz music. The original campus silhouette is fused with a blue in green colorway, a lot like an unexpected jazz riff. Think these colors are a coincidence? Then you don't know the Miles Davis song “Blue in Green.”

I just got these handmade English shoes myself and wear them all the time. (They're a lot more comfortable than Doc Martens out of the box too.) I style them with fatigues, straight-leg denim and fleece sweats—there are no rules to this. Electing to go with the single monk elevates the shoe in my opinion and gives off an even more knowing, sophisticated look.

I've never met a suede and leather shoe that I didn't like, and these are no different! The olive green just screams Fall and the versatility of it toeing the line of casual and dressy is the best. Cut from Horween suede, they're grounded with a comfortable camp sole. Rock these with your favorite navy chords or some pleated chinos for a laidback professorial look.

Woolrich is known for its longevity with outerwear, but what about footwear? Most hiker boots always teeter the line of being too functional and not stylish enough; however, these are both. The cool grey suede is incredibly modern. Plus, a water-resisting upper and a Vibram rock outsole? The elements don't stand a chance.