So without further ado (and hopefully, with improved writing skills since I first shared my advice in 2007), here are my updated tips for how to wear high waisted:
Fit is first. Achieving the right fit is key to pulling off high waist styles with panache. The waist should be fitted but not tight. Conversely, the waist should not be too large with gapping in the back. If you're wearing pants, denim, or shorts, the hip and thigh shouldn't tug or create excessive horizontal creases. In the fitting room, make sure you can comfortably sit down.
Choose fabrics that flatter. Ideally, you want some stretch, but not too much. High waisted jeans that stretch up a size and become baggy are undesirable, so look for fabric content with no more than 2% spandex or lycra so that it will retain its shape.
Pocket placement matters. When choosing high waisted denim, look for back pockets that aren't too big or too small for your backside, as they can create the illusion of a bigger butt. Back pockets that are placed above your leg crease will ensure that you don't appear to have a saggy bottom. Among my preferred brands are J Brand and Cheap Monday for their flattering fits and comfortable fabrics.
Get longer legs and score style points. Fortunately, high waisted styles visually elongate the legs, so to enhance this effect, pair your wide-leg or palazzo styles with height-boosting platforms or wedges. While I love wide-leg styles with heels to counteract the volume, I think skinny-fit bottoms look chic with flats and low to medium heels (under 3"). I find that cropped, high waisted denim is elegant when paired with a tucked-in blouse and pumps or ballet flats. A flash of skin at the ankle can also elongate the leg when it comes to wearing cropped, high waisted skinnies.
Show off that waistline. If you're wearing a long, loose blouse, then tuck it in and pair it with a skinny belt to highlight the waist. Experiment with half tucks and partial tucks (see J.Crew for inspiration) if you desire a more nonchalant look. If you're more daring, pair your high waisted bottoms with a crop top to show off your midriff. Still stumped on how to style your shirt? Button-front tops look cute tied in a knot, as I did with my chambray shirt above on the lower right.
Picking prints and washes. When it comes to high waisted denim, dark washes can be dressed up more easily and are more slimming. Treatments such as whiskering and fading draw attention to the areas in which they are placed. For printed bottoms, horizontal prints can be harder to pull off, as well as larger prints. Opt for subdued color schemes, vertical print placements, or smaller prints if you want a visually slimming effect.
See my favorite high-waisted styles: