Boyfriend jeans might be the item of clothing least understood by the male sex besides harem pants (no offense to Elizabeth Monson who happens to be wearing an adorable pair today from Topshop). So you can imagine our surprise when the leggy Whit was spotted in the West Village wearing ripped and destroyed boyfriend jeans instead of her usual jeggings (the spawn of jeans and leggings), a mini skirt, or shorts. This is one of those outfits that girls love and men hate; nothing repels a guy more than boyfriend jeans, an oversized t-shirt, and jazz shoes.

(Yes, I'm wearing a modified version of Whit's ensemble right now.)