No one likes getting pigeonholed by their clothing -- just because you wear a striped shirt doesn't mean you're a jerk, and just because Pete Wentz wears skinny jeans doesn't mean everyone else who does wears eyeliner. For clothes that impress and perplex, try Kendi
Kendi makes refined gear inspired by the desire to "defy wardrobe expectations" in a playful manner (to defy in an alarming manner, try the no-pants dance). Their skinny ties, cut classic or dagger style, are sourced from unconventional materials like acid-washed denim, seersucker, brushed-cotton buffalo plaid, and bandana fabric -- for rocking the Prep Michaels look, minus the skanky girls, and really nice wig. For your torso, Kendi's taken their collection of slick-but-traditional, slim-cut dress shirts (black/gray houndstooth, white cotton, etc) and sewn in matching hoods that droop low over the eyes, simultaneously giving you the air of a white-collar criminal, and a no-collar criminal
Kendi also purveys shorts that rise perilously close to mid-thigh, but whose khaki and contrast-stitched denim keep them stylish -- just because you like to let your legs breathe, doesn't mean you coach PE.