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.
Make Sure They Fit
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.