Hot or Not Ashlee Simpson's:It's dangerous work, being a trendsetter. Over the weekend, Hollywood hipsters Pete Wentz and Ashlee Simpson-Wentz hit up a birthday party amid a small crowd of photographers. Ashlee, who has been at work on her fourth album, was outfitted in a decidedly trendy take on denim cutoffs, a summertime staple.

Simpson-Wentz's shorts were high-waisted and extremely short, with the white front pockets showing. The performer attempted to make the look less racy by pairing the cutoffs with ballet flats and a roomy sweater, but the overall effect was still pretty jarring. Is Simpson on the forefront of a trend, or is she trying too hard?