Alison Wood brilliantly blends her hometown Midwestern spirit, New York cool and Italian sensibility into her designs. The Alison Wood Bowery Bucket Hobo is a perfect example. Made of Italian lambskin leather, this bag comes in the perfect shade – a lovely distressed leather that gives of hues of black, brown and gray. Multiple horizontal zippers add just the right amount of detail and downtown cool to this otherwise simple silhouette. Basic with a touch of flair.

$500, Bergdorf Goodman