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Wearing Leggings: A 'How To' (and How Not To) Guide

Posted by Nora | Wednesday October 27, 201031 comments

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
More by Nora
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on February 01, 2011  dolce_bellissima  4,214 said:

I live in leggings...NOTHING is more comfortable, and thank goodness for great brands who have really upped the design and materials in them to make them look good dressed up. I have lately had a huge infatuation with lace leggings- I cannot get enough!

on October 31, 2010  Say no to cropped leggings! said:

I'm surprised the cropped ones are popular anywhere. I think they look good on about 5 people because you need to have great calves to pull them off. I guess it all depends where you live for that trend. I totally get the other ones. They're so comfortable and go with everything.

on October 30, 2010  mamaluv  STAFF said:

Yup, in the southeast cropped leggings are practically epidemic

on October 29, 2010  flowerfaerie  366 said:

Rachel Bilson looks great, Whitney Port looks ridiculous, Megan Fox can pull it off (ish) but I doubt many people can without looking sleezy, and I don't think I need to comment on Renee Z.

on October 28, 2010  Nora said:

becky i <3 you.

ali and mels and mamaluv...trust me, in the midwest the cropped leggings are still cropping up. ew, wordplay.

on October 28, 2010  mamaluv  STAFF said:

Well... I hate to say it but in less fashionable cities, they are indeed wearing cropped leggings. Hence the need for public awareness ;)

on October 28, 2010  Becky  13,113 said:

Wow i love love looove this article!!!!! I actually learned something (a lot of somethings) reading this!!! Omg I can't wait to dress up for work tomorrow!!! :) :) :) :)

Nora, gf you should totally do these sorts of articles like every 3 days ..teach us (or amateurs like me namely) how to dress :) xoxo

on October 28, 2010  Ali de Bold  STAFF said:

Mels, LOL! Too funny. I love that you said that in italics. That particular type of leggings was a really hard one to find pictures for. That should say something. Not many people are wearing it!

on October 28, 2010  Mels  551 said:

Honestly.. Renee Zellweger is hardly a fashion item.

on October 28, 2010  pamela @vampiresmitten said:

Rachel pulled it off best out of all of them. I love love love her style

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