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How to Wear Leggings

Shirt: Gap, Vest: Lit Boutique, Leggings: Kohl's, Boots: vintage Walter Steiger, Belt: H&M, Earrings: Toots & Magoo, Sunglasses: Urban Outfitters, Cuff: c/o Ann Taylor
It seems like leggings are everywhere - they came back, and they stayed back. I admit, I was skeptical at first, but I've come to embrace leggings, styled properly and worn in the proper situation. I recently received a reader request asking for some ideas on how to wear the leggings / tall boots look, so I put together a few pointers!

The most essential factor is the leggings themselves. You want them to fit tightly, though not circulation-stifling. Conversely, avoid pairs that are too loose; it's not going to look good if they're slouching on your legs. 

Fabric is also important! If you can see your skin (even a little bit) through the leggings, then you should think of them as tights. And tights are not pants! I cannot stress this enough - when purchasing leggings, try them on, or at least put your hand inside the fabric so you can determine the thickness of the weave. Many cotton leggings are thick enough, but you can also look for leggings in wool, and, if you want to feel really luxurious, cashmere. 

Dress: thrifted, Sweater, swapped, Leggings: Kohl's, Boots: vintage Walter Steiger, Necklace: Shop Mamie, Sunglasses: Urban Outfitters, Watch: Michael Kors
Once you've settled on leggings, it's time to style the rest of your outfit. Keep your tops long and somewhat loose; leggings and tanks or crop tops are for the gym only! If you pair them with a longer tee, add a scarf, sweater or jacket to keep the look from becoming too sloppy.

Leggings work well for layering - pair them with a dress that would otherwise be scandalously too short (like the photo above) for a look that is lesson in style, not anatomy.

A flat or low-heeled tall boot is perfect paired with leggings - it offers some coverage on the leg and helps balance out proportions. Ankle boots of varied heights can work, too, just make sure the legging is tucked in. I prefer to match the color of my legging to the color of my short boot. 

Like these tips? Want to get a great pair of leggings? Here are a few suggestions on where to purchase
See more How To's on the TBF How To page

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Shirt: Forever 21, Sweater: Ann Taylor, Leggings: Kohl's, Boots: vintage Walter Steiger, Necklace: Shop Calico, Necklace: Bridesmaid gift, Sunglasses: Urban Outfitters, Watch: Michael Kors

How do you like to wear leggings? Have you found a great brand or style?

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  1. I like to wear leggings. I wear them with short dresses that are toooo short :D or with long sweater.

  2. Kristen, great tips and your outfits look fab! My favorite leggings are the Danskin ones. The right amount of tightness and thickness. Happy Friday!

  3. @Lissy Danskin! Yes! Great idea, Lissy!

  4. Hahaha TIGHTS REALLY ARE NOT PANTS - how many times have we seen these on the streets?

    You look amazing - thanks for the leggings tips! I love the ones I got from Aritzia in Toronto way back. They've not faded or stretched out in the least.

  5. good advice! I only wear leggings with longer shirts or little dresses. I wish more people would take that advice!

  6. I love a good pair of tights. Quality is everything. It's so true. If I see one more girl in tights but no pants I think my head might implode.

  7. Anonymous11/04/2011

    I, too, was skeptical about tights/leggings initially; now, I don't know what I'd do without them. Good ideas, here!

  8. Ooh that last look is one of my favorites! I totally agree with you - we should really all do our part to stress the fact that tights are not pants!

    Hope you have a wonderful weekend! :)

    sorelle in style

  9. You know, it seems like common sense to try on leggings and make sure they aren't too sheer but man, do so many people make this mistake. You want to tell them....but how does one bring that up? Great tips!!

  10. Love the looks you chose! I love leggings and happily invested in a great, thick pair! Awesome post girl!

  11. I simply love these leggings!
    Love your blog btw.


  12. Anonymous11/05/2011

    Great legging tips. I love the way you styled them. I agree about thickness of the tights and length of the top. So crucial!

  13. Loving all 3 looks but i think the 3rd is my fave! And I guess i need to take a trip to Kohl's this week...cord leggings are calling my name!

  14. Oh thank you thank you! I love that you posted places to buy Leggings. Looks like I'll be hitting up Kohls soon!
    Now if you find a place that sells LONG tshirt/tunics - please promise to tell us. Finding a shirt long enough to cover up my booty is definitely a challenge. Until then I'll be pairing my leggings with short dresses!

  15. Hi. You look awesome. You have paired with boots.

    Check out my style. Even I am wearing leggings?

    Really nice blog? Do you wanna follow one another?

  16. Love your legging outfits. I like American Apparel's leggings. I wear them with tunics, dresses and skirts with boots and flats - so comfortable!

  17. Great post, and I totally agree with all of your points... I was also pretty skeptical about leggings when they first came back, but now I consider them something of a staple: you just have to be careful what you wear with them!

  18. @Erin Blair Gobin That's definitely troublesome - especially since pretty much ALL shirts are long on me since I am 5'2". Baggy sweaters will also work well...

  19. i LOVE this post! it drives me insane when grown women where leggings as pants, they are not pants!! there are definitely lots of fun ways to wear them tho and be appropriate! i love your options :)



  20. Great tip ideas of how to wear leggings lady!! But can I tell you how crazy in love I am with you boots. They're absolutely gorgeous.

    Thx for the tips.

    <3 Marina

  21. Great post! Can you make this into a PSA? Most people don't seem to know how to wear leggings appropriately...

  22. I love leggings! They are great for transitioning items!
    Shasie of Live Life in Style

  23. Everyone needs to read this. These are great tips that every girl rocking a pair of leggings should know. Great blog! Love seeing this coming from the Boston area, it's great to see what's trending.

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