Once the purview of Nelson Algren, Wicker Park has been disparaged as "hipster central" but take it from someone who grew up in the 'hoods pre gentrification - this is way cooler - and safer. Snag an Eastwood hat, Inspired by classic Americana western films, at Wayward and browse wool pea coats and signature Perfecto motorcycle jackets at The Chicago Flagship of Schott NYC. You'll find trendy fashion at Fab'rik, Current/Elliott and Oak + Fort. Stop in Velvet Goldmine for Mid Century Modern furniture, housewares, barware, pottery, clocks and artwork; and there's fine vintage decor and womenswear at North Avenue Collective. The area is a magnet for artists who work on the canvas and the plate so don't leave without having a bite and a pint. Better yet, plan to visit during one of the annual events like the WPB Summer Sidewalk Sale; Chillfest; and Wicker Park Fest.