Legging tips for pear-shaped women If you have the classic pear-shaped body (small on top, bigger on bottom), your first inclination might be to avoid leggings altogether. Worn the right way, however, leggings can be a fashionable and flattering look. Think Kim Kardashian. Ankle-length leggings are a staple in Kim's wardrobe, paired with a long tunic layered with a jacket or cardigan. Try a chunky ankle boot with a small heel to give your outfit a little extra sass.