While Audrey Hepburn and her small dancer's frame famously made leggings and ballet flats appear chic, it can be tricky to seamlessly pull off a polished leggings look. Plain stretch-cotton leggings should mostly be relegated to athletic wear; they should never be worn in place of pants, as their snugness leaves little to the imagination. But leggings in luxe fabrications like leather, sateen or velvet are more structured and can be appropriate for dressy occasions.
Maximize the Mini
Leggings present the perfect opportunity to sport a minidress without baring too much skin or restricting your movements. For a holiday or birthday party, try a sparkly or beaded minidress with sateen leggings and heels. For a night out on the town, pair a fitted T-shirt minidress with leather leggings, high-heeled booties and a statement necklace.
Dressy leggings pair beautifully with a long button-down top or long flowing tunic that covers your backside. For dinner-party look, rock leggings with a sequin stripe down the side; wear them with a long silk shirt or drawstring top, metallic bangles and heels or shiny flats. Double-knit leggings can be worn with a long cotton peasant blouse or chambray button-down shirt and your favorite boots for a picnic or outdoor affair. Cinch the middle with a leather belt for more waistline definition.
Layer With a Blazer
A blazer or structured jacket helps pull most any outfit together, and can easily make a pair of leggings look sleek and polished. Wear leather leggings with a long silk shirt, sharp fitted blazer and d'orsay pumps for a sleek ensemble appropriate for a dinner date or a creative office environment. Twill leggings are a good alternative if leather is too flashy, and they also work on weekends with a tweed blazer, classic white shirt and riding boots. Play with proportions -- either sport a shorter shirt and long blazer, or try a long blouse with a cropped jacket for an edgier look.
Don't Sweat It
When in doubt, an oversized sweater is a chic and comfortable way to pull together a leggings look. Layer a cotton or silk shirt with a long belted cardigan over leather or knit leggings, or try a long chunky-knit pullover sweater instead. Dress up your ensemble with a scarf and heeled boots, or keep it more casual with a necklace and flats.