Newsflash from 2007: Did you know that instead of wearing pants with buttons and zippers, you can actually wear LEGGINGS? It’s true. 

Jump forward to 2010: now that leggings are sold everywhere, it’s as if we’re living in a lawless, leggings-based society. Just because you can wear your favorite fifth grade staple as a full-on grown-up doesn’t mean you don’t need to put some effort into it.  Like everything else, there are rules to wearing spandex-based clothing. 

Rachel Bilson, Whitney Port

Work Leggings

Those of you stuck in corporate jobs that require ladysuits, pantyhose and other staples from the 1990s can skip this portion.  For the rest, take note.  There is one cardinal rule surrounding leggings at work: Thou Shalt Not Show Butt Crease.  Once your coworkers see your perfectly outlined butt cheeks exposed, you can check your credibility at the door. 

I tend to skew a bit hipster, but I like my work leggings with a hint of professionalism.  Adding a boyfriend blazer to a tunic top and boots means you’re ready for business (casual). 

Topshop Flannel Camel Boyfriend Open Jacket (US$135), Delias Avery Ruffle Tank (US$20), Shape FX Skirted Control Leggings (US$50)

Date Leggings

For a first date, leggings walk the line between casual and sexy so you feel confident whether you end up at dinner or a dive bar.

Leather (or pleather, let’s be real) leggings are glamorous, bad-ass and double as a lower-body corset that magically hides that five pounds you gained from eating fistfuls of peanut M&Ms every time you pass the receptionist at work.  Paired with an oversize men’s white T or a beat-up flannel they look casually hot.  Add some heels and some layers and you look like the long-lost Olsen twin.

Spring Greenbacker Necklace (US$10), H&M Top (US$24), French Connection Leather Look Leggings (US$128)

Tricky Leggings

Lace leggings are a tricky beast.  Worn the wrong way, you instantly look like an extra on Saved By The Bell: The New Class (you know, the one that nobody watched).  Done right, you look like a certified, card-carrying Total Babe.

Megan Fox

Yoox Liquid Street Love Scarf (US$50), Vanessa Bruno Cotton-Blend Sweater Dress (US$144), Romeo & Juliet Couture Black Floral Lace Leggings (US$27)

Renee Zellweger

Cropped leggings fall into a special category called, This Looks Good On .0003% Of The Population.  This is good news if you’re as long and leggy as Gisele, but it can be hard to pull off a pair of pants that cut off at the widest part of the calf (we’re looking at you, Zellweger).

How do you wear your leggings?

by Nora McInerny