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What to Wear With Leggings: 10 Polished Ways to Style the Tricky Staple

What to Wear With Leggings: 10 Polished Ways to Style the Tricky Staple

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    1. With plenty of layers.

    Leather leggings aren't going anywhere this fall, and look best when paired with lots of layers on top. Try throwing a patterned sweater on over a monochrome button-up, then putting on a utility jacket or oversized blazer. This look also works with plain black lycra legging, too.

    Image via Elle

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    2. With a basic button-down.

    When it comes to leggings (leather or otherwise), the simplest route is to pair them with a slightly oversize solid button-down. Try to stick to a darker color legging (black being the most obvious choice) and contrasting them with a blouse in a white, pastel pink (this season's It color), or another light tone. Throw on an oversized blazer and some oxfords to finish things off. 

    Image via FabSugar

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    3. With a big chambray top.

    Behind a classic button-down and a blazer, the loose-fitting chambray top is your next best choice for pairing with leggings. They key here is length: if it's too short (i.e., hip-length), it's going to look odd. Remember: leggings are not pants, so you shouldn't wear tops with them that you'd wear with your favorite pair of tight jeans. The chambray should hit at mid-thigh or so.

    Image via Long Hairstyles

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    4. With motorcycle boots.

    One of the hardest things about wearing leggings is figuring out what to put on your feet, but when the weather cools down, it's all about the boot. No platform sandals, no wedges, no stilettos. Leggings look chicest in the fall and winter, and really work best with a great pair of moto boots. 

    Image via Fashionfreax

    Photo: Stylecaster Pictures /
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    6. With a statement boot.

    Perhaps the best way to dress up a pair of leggings, making them appropriate for Fashion Week or even just a nice dinner out, is to rock them with a pair of statement boots. The statement can be a fierce one, such as with these cow-print booties, or it can be a little more subtle: a chunky ankle or knee-high boot with a thick high heel will suffice just fine.

    Image via Stockholm StreetStyle

    Photo: Stylecaster Pictures /
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    5. With an oversize coat.

    Once the temps really start to drop, many people mistakenly rule out leggings from their wardrobes. But they can keep you warm if paired with a heavy, oversized coat. If fur's not your thing, try a big pea coat

    Image via Refinery29

    Photo: Stylecaster Pictures /
  • Celebrity Sightings In London - August 19, 2013

    7. With a long T-shirt or mini dress.

    Gwen Stefani can wear just about anything and look chic, but her look is not reserved for celebs with rock star-level style. Instead of reaching for a generic tunic, try an extra-long T-shirt or mini dress in a vivid pattern, finished off with ankle boots.

    Image via FilmMagic

    Photo: Stylecaster Pictures / FilmMagic/FilmMagic
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    8. With sparse embellishments.

    The most common style mistake we gals make when trying to rock a pair of leggings is going for as many loud prints, embellishments, and cutouts as we can. If you simply must jazz up those stretch pants, go for something sparse and subtle.

    Image via Le 21ème

    Photo: Stylecaster Pictures /
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    9. With neutral prints.

    Along the same lines as embellished leggings, if you simply have to have a pair with a pattern, avoid neon prints. Instead, try a pair of jeggings in a cool tribal or tie-dye motif fashioned with neutral colors. And make sure to pair 'em with muted colors on top, too. 

    Image via Stockholm Street Style

    Photo: Stylecaster Pictures /
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    10. With socks.

    Yes, you can wear leggings with socks! Just make sure you coordinate your them with the rest of your outfit. This example works well since she stuck with varying shades of tan with her black leggings and black booties. 

    Image via Urban Weeds

    Photo: Stylecaster Pictures /

Ah, the age-old question: what to wear with leggings? Sub-queries include: “Can leggings be worn in place of actual trousers?” (Nope!) “Can I wear them with pumps and a tank top?” (Uh, no.) And finally, “Can I wear those crazy, neon-patterned geometric leggings lining the walls at Urban Outfitters to work? (They’re a no-go.)

MORE: How to Wear a Full Skirt: 7 Ways to Rock the Feminine Piece

The confusion surrounding leggings is made all the more ironic by the fact that during the last few years, they’ve established themselves as one of fashion’s most prominent trends (they’ve even bred jeggings, the ubiquitous denim-legging hybrid.) But the fact remains that most of us are guilty of having no clue what to pair them with in order to create a sleek, stylish outfit.

MORE: 50 Fashion Rules To Break Right Now

Well, the confusion stops here, ladies. Click through the gallery above for 10 polished ways to style the tricky staple this fall, with a focus on what exactly to wear on top and on your feet. Finally, leggings freedom has arrived!

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