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There is an endless plethora of advice out there on how to wear leggings. And the fact is, most of it is wrong. As of spring 2011, leggings aren't considered a "risky" fashion choice, but a wardrobe staple that can be dressed up or down for any occasion. Younger women are wearing leggings out at night to the club and more conservative ladies are finding ways to sport them at work. The shoes you wear with your leggings depends on what kind of look you're going for.
You could put on flip flops or boat shoes, but honestly, not if you want to look cute in leggings. If you want a simple, feminine vibe, pair leggings with ballet flats. A darker color of flats will elongate your legs. A neutral or light pink color will call to mind delicate femininity. This look channels one of the most classic styles known to women: Audrey Hepburn a la "Roman Holiday."
If you're more the punky, sporty type, throw on a pair of simple Keds-style lace-ups or Converse. If you want to look edgy while you're picking up fluffy from the dog groomer, throw on a pair of motorcycle-style boots. Either way, you're choosing a youthful, fun option that is also chill and relaxed.
Girls Night Out
Times once were that fashion gurus discouraged you from wearing leggings as pants, as well as guffawed at the idea of wearing them with a pair of heels. But the young, fashionable set has changed all that. Shiny, liquid leggings paired with soft, feminine tops have been ruling the night time scene in both New York and Hollywood. Now, shiny leggings aren't for everyone, but black, matte leggings are. So, pull yours out, put on a tunic or silky top and head out in a pair of simple, pointed or round toed platform pumps.
At The Office
Today's offices are much more casual than they have ever been. I'm not saying you should wear leggings when your executive is in from New York, but on a typical office day, they work. Avoid wearing them as pants and instead make sure you've got a dress or tunic that covers your back end. Put a cardigan and/or blazer over top and wear with a pair of riding boots or knee-high moderate heeled boot. In this case, you want to stay away from high heels with leggings as well as sandals, which are too cheeky for your 9 to 5.