5. Orchard Skateshop
OK, so maybe the giant halfpipe skate ramp in Orchard's Allston location was a little intimidating, but fear not. The newly opened second home in Back Bay still sports a stellar selection of kicks (Vans, Huf, and Supra amongst them), hats and hoodies that don't require you to reenact the X-Games.
297 Newbury St., Back Bay (617-232-4300)