Make Sure They Fit
A Cautionary Tale

Poor Jessica Simpson. In one 2009 concert, she might have done more damage to the reputation of high-waisted pants than the entire 1970s ever did. Clad in an ill-fitting pair of jeans cinched by a wide leopard-print belt, she did her curvy figure no favors.

Once you've decided on a style of high-waisted pants, you can't settle on just any pair -- they have to fit absolutely perfectly. Even the most expensive, well-made designer jeans will suddenly look mom-esque if they're too short, pulling across the hips or sagging in the crotch. So if you love a pair that's just a little bit off in the fit department, get them tailored. It'll be well worth it.