Reader Request: How to Wear Leggings

How to wear leggings - tips and advice!

Looking for advice on buying quality leggings? Try this post!

Julia asked:

I’m not sure if this has been discussed, but a post on a “how to wear leggings” would be fantastic! Leggings are so comfortable and you always looks great in them. I have a couple pairs but I struggle with how to wear them. Maybe you could help with a few guidelines on shirt length?

Did you hear a happy sigh just now? That’s me warming to this question. I adore leggings and they are my go-to weekend choice for ultimate comfort. Not all women dig the look, but I do. Big time. In fact, I believe that leggings can look fantastic on a huge variety of body types, which just makes me love them all the more.

OK enough gushing. Let’s talk about how to make leggings work. As always, these are my personal guidelines for wearage … and even I don’t follow them to the letter! Pick and choose as suits you.

Already Pretty outfit featuring knit moto jacket, aymmetric tunic leggings, fringe handbag, black ankle boots

I consider leggings to be casual bottoms and wear them as such. There are plenty of office environments laid-back enough to accept leggings on a daily basis, but none of my desk jobs ever felt like leggings-all-week places. They were my jeans alternative, and only worn to the office on Fridays.

They are absolutely ideal for those who live highly active lives and sport casual style on a daily basis. Moms to young kids, anyone who works with animals, fitness instructors, etc. And I firmly believe that women of all ages can sport leggings, if they love them and wanna rock them.

Already Pretty outfit featuring brown sweater dress, brown leggings, John Fluevog Adriana Luna, distressed leather messenger bag

I have seen arguments for leggings as actual pants. I don’t believe they are, and prefer them worn with tunic- or dress-length garments on top. There are plenty of tight, sassy pants available that have a little more structure and formality, and provide a little less information about your anatomy. This is a rule I follow quite strictly myself. If I were to wear leggings as pants, you could literally see how my ladyparts are shaped. ALL OF THEM. So I just don’t.

The sweater dress shown here is a great length for me to wear with leggings. It’s short enough to show lots of leg, but not so short that it hits me at my widest part. If you’re looking to make your legs look as slim as possible, choose a top that hits you in a similarly sweet spot: Somewhere above your knee, but before your thigh widens and starts to become butt. At least two hand-widths above your kneecap is a good guideline for most folks.


Already Pretty outfit featuring cargo coat, blanket scarf, tunic, leggings, tall black boots

I certainly don’t abide this rule all the time, but when I’m hoping to make my legs look as long as possible, I’ll pair leggings and boots/shoes in similar color palettes. Black leggings with black boots means black from high-thigh to toe. A nice, long, unbroken line. Fantastic if you are concerned about shortening yourself up.

NOW! Let’s talk about legging-shoe pairings, shall we?


Already Pretty outfit featuring Comfy USA striped tunic, black leggings, chain booties, black fringe handbag, long pendant necklace

This pairing can be leg-shortening, especially when they’re in high contrast to your skin tone, as mine are here. But the look is arty and fun, and comfy as all get-out. So if you don’t care, go there.

Ankle-length leggings also look smashing with pumps and sandals, especially low-vamp styles. I don’t believe I’ve ever paired them myself, but have seen other women do so to great effect.

Already Pretty outfit featuring red sweater tunic, leather leggings, tall black boots, fringe handbag, beanie

OK, I’ll admit it. There is no difference between ankle-length and full-length leggings. The only leggings that go longer than ankle-length are stirrups and I don’t own those. Yet. ANYHOO. I am my happiest in a pair of long leggings and a pair of tall boots. Comfy, cozy goodness. As always, a monochrome pairing will be the most elongating.



Leggings look fab with giant socks and clonky engineer boots, but they can also look sleek and chic just on their own. As is the case with taller boots, those big socks will add warmth and another fun layer, but also bulk. If you prefer a trimmer look, go without.


Already Pretty outfit featuring Iceland sweater, leather leggings, Rebecca Minkoff Logan, black ankle boots

  • Leggings are not the same as tights. Tights are more thin and sheer, and generally encase the entire foot. Wearing thick leggings with a flirty sheath dress will likely look a bit odd.
  • To each her own, but I vastly prefer cotton-blend leggings. The nylon/spandex ones are hot, and remind me of figure skating costumes.
  • If you have issues with leggings that ride up your calf, tucking them into your socks will definitely help. Or if you’re wearing boots, a pair of thin socks that are hidden by the boot will secure the legging.

Hope this is helpful! Looking for advice on buying quality leggings? Try this post!

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details. Sustainable options are either used, handmade, made in the U.S., artisan made in non-sweatshop conditions, or made using sustainable/fair trade practices.

Originally posted 2010-09-15 05:16:00.

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59 Responses to “Reader Request: How to Wear Leggings”

  1. Chalkdust and Boots

    Thank you for this! I just bought (and wore) my first pair of leggings since 9th grade (which was…a while ago) and I'm still a little self-conscious about wearing them all. I'm gonna try to become one with your suggestions!

  2. Lauren

    I only ever wear leggings with ballet flats. I know I'm not "supposed" to because of my petite height, but ultra-comfy cotton-blend leggings + ultra-comfy ballet flats = happy Lauren.

  3. La Historiadora de Moda

    These are great tips, Sal! And I strongly believe that leggings are not pants.

  4. Sal

    Lauren: GOOD! I hope I've made it abundantly clear here that these a guidelines that you should take or leave at will. Screw "supposed to," and wear what makes you happy.

  5. Erin

    I LOVE leggings! I like to wear dresses more than jeans, but I bend over/crouch/kneel/etc. all the time at work. Leggings give me the butt coverage (and confidence) that tights don't! Plus I can wear short dresses with no worries!

  6. tigerteacher

    I enjoyed this post a lot! I'm a recent legging convert. I'm not a big fan of above-the-knee length skirts and dresses for myself because I hate tugging at my skirt to keep myself comfortably covered whenever I sit down! But leggings have made me more comfortable with some things of this length.

    Also, I do have a great source for nice leggings on the cheap: Rainbow Shops. I wear a plus size and if you stick to Lane Bryant, etc. you can easily spend $40 on a pair of leggings. Rainbow usually has them closer to $5 a pair and lots of colors and textures.

    • sue

      Hello and thank you for the wonderful information. I am going to give this a try. How do I find the Rainbow Shops you were talking about?

  7. orchidsinbuttonholes

    First, I love the looks you paired with this very helpful guide, but my favorite favorite favorite is the one with the printed full length leggings and short boots. Love that – it's edgy and pretty.

    I usually wear my full length leggings with ballet flats, but I love the difference a heel makes to the same outfit. I think that's the cool thing about leggings – they go with so much and can be worn on many different occasions.

    Great post!

  8. Future Lint

    I don't think I'll ever do the legging as pants thing. I totally abide by the "tunic or dress MUST cover my whole butt" in order for leggings to be worn. My only problem with leggings it that when I wear them under too-short dresses, they tend to come off as juvenile on me… I don't know what it is… I think I just need to experiment with color and length a bit more (I only have 3 pairs of leggings, so my options are pretty limited right now!) But for the cold winter, I think I need to invest in a few new pairs since they are warmer than tights!

  9. Charlotte

    ok, i am a new reader and I think your blog is FAB! FAB FAB FAB. now that I have that off my chest, I want to say thank you for this post. (I graduated from college in 2004, feeling pretty stylish, then I went to law school and got a miserable job in a very traditional firm that did not tolerate stylish dress. When I emerged from that dark period in my life in 2009, I was so confused because tops were longer, pants were skinnier, necklaces were chunkier, everything changed!! ) Anyway I am trying to get back into the swing of enjoying my wardrobe and I am inspired by your style. 🙂

    What is your take on jeggings? Also, I have a figure like yours (hourglass with a bit of a "tum"). My jeans and A-line skirts hold me in and hide the tum but I noticed you wear dresses always with the leggings. BRINGING me to my poing. hehe. Any tips on hiding the tum while wearing leggings??


  10. Elissa Glyn

    I'm a grad student, and the undergrads at my university seem to all wear leggings with long shirts and Uggs. I have avoided leggings because I don't want to dress like the undergrads I teach, but your pairings are very tempting. I might do some experimenting, especially with the long cold winter on its way.

  11. Mrs.M in MI

    A word of warning: Please make sure your leggings are really truly opaque, especially if you choose to wear them as pants.

    My sister-in-law and I were at the movies this summer and there was a girl who thought her leggings were much more opaque than they were. Now, she was wearing them as pants, which is mistake #1 in my book, but when she bent over we saw her underwear and ENTIRE anatomy in sparkling clear detail. Yikes.

  12. Kafine

    Thanks for "leggings are not the same as tights". I have seen so many people around wearing these footless tights things with short tops, apparently mistaking them for opaque leggings, every aspect of their undercarriage plainly visible to the general public. Hrm. Flattering.

  13. becky f.

    Thanks for the tips, Sal! Last winter was my first experimenting with leggings, and I liked them more than I expected. I also wanted to add that there is a difference between ankle-length and full-length if you're very short — my 24" inseam means that full-length leggings are pretty much leggings + socks for me. 🙂

  14. Diana

    I wear cropped leggings under short skirts with sandals, and long ones under dresses and skirts with boots. I really want to try the long leggings (especially the ones with cool zipper/button details at the cuffs) with non-boot shoes, but I can't wear ballet flats and generally have problems with closed-toe shoes without socks, so I'm a little stumped about footwear…

    Also, leggings are definitely NOT PANTS! I am kind of paranoid about people thinking that I'm wearing my leggings as pants, so I'm even leery of long tunic tops that don't look like dresses… a very short dress for some reason is fine though.

    A good trick for the cropped leggings is to push them up a little so they end ABOVE the widest part of your calf, which is very flattering.

  15. Louise

    Great informational post! I just got some GREAT denim leggings from Old Navy of all places! For SIX bucks! The original price is only 14.50. They are so soft and just look like denim, but they are really just cotton and poly and spandex. Okay, this comment sounds like spam, but it isn't, I promise.

    Thanks for the tips!

  16. LAP

    I just want to say great post. There's something about wearing leggings that make me feel extra secure. They're like an everyday superhero costume, especially if they're in fun colors. As a plus size girl, I can't recommend the Vera Wang footless tights and leggings from Kohl's enough. The XL never give me a problem with crotch hang, and I am just tall enough (5'8") that it can be a considerable issue.

  17. amal

    Where do you get your BOOTS?!!!!??? so fabulous. the pair in the last photo, especially! thanks for post,

  18. Sal

    LAP: Man, me too. There is something so comforting and secure-feeling about pulling on a cozy pair of leggings.

  19. Julia

    Thanks so much for addressing my question, Sal. I love your look in each outfit – thanks for all the great info and detals! I'm excited to try my hand at some of these styles.

  20. Sal

    amal: The last pair are Diesel, a style called Go-go, which were purchased two years back. You might be able to find a pair on eBay.

  21. Julie at MDMA

    I'm happy to see your white tights with white tunic/dress! I have put that combo on 10 times but abandoned it before I left the house because I felt so "nursey." It looks great with a pop of color on top … it's still hot here so my window for wearing white AND a second layer on top is limited but I'm going for it.

    Thanks for the great tips. Have we seen where you keep your shoes? You must have a warehouse to keep all those pairs of fab shoes…

  22. grace

    A quick suggestion for tall girls who want full-length leggings–Victoria's Secret has a pretty good color palette in their yoga leggings, with a 32" inseam.

  23. GlamaRuth

    I had lots of leggings the first time around (elementary school), all worn with matching giant shirts, and I like them again (and so much better!) in their modern incarnation. I do use them in lieu of (or over) tights on really cold days. I'm also lucky enough to be able to wear them to work on non-meeting days, though nevah evah evah as pants! I also love jeggings because they are actaully fitted enough on my bony ankles as slim jeans never are (esp as I always have to hem them, and lose a lot of the taper). Still not really pants though – if they are heavy enough denim, you can go a bit shorter on top, but it still must skim the hips and absolutely cover the waist, because even 15 year old Kate Moss would have muffin top in elastic-waist denim.
    My favorite plain cotton leggings are by Rebecca Beeson, but I bought them at TJ Maxx for about $12. If you want to splash out a bit, go to I Heart Norwegian Wood on Etsy – Angie will work with you to custom make amazing leggings. My two pairs have insets of different fabric at the knee, or faux-leather knee patches (I think she calls the style "winter warmer"), and she used my measurements to make sure they fell correctly on my legs since I'm a shortie.

  24. Marianne

    I've still not tried the leggings look, probably every girl I went to college with wore calf-length leggings under denim skirts, so they always make me think of boring sorority girl style. This tutorial, though, makes me want to start experimenting…

    Also, reading Corporette the other day made me realize how grateful I am that your body-positive blog exists. A post about jeggings attracted some commenters who were horrified that "fat girls" thought they could wear jean-leggings. Ugh.

  25. text machine

    I like leggings as a warmer tights alternative. I have ventured out in my full length leggings and flats on occasion. But I really can't get behind the mid calf or knee length leggings. I don't think it does anyone any favours. There's something a bit tacky about it to me, somehow. Why not just wear the long kind and avoid chopping yourself into a million pieces? I understand sometimes you just need a layer for decency and it's hot and you don't want to be covered. Now that it's fall, however, I'm strictly anti.

  26. Stephanie

    I just started wearing them again this spring when I found your blog. I do use them as a tights substitute but my life is much more casual then yours and I find that leggings hold up better then tights do for a sahm who likes to run around bare foot at home.

  27. MelD

    I see Diana already made that comment I wanted to add: pushing the cropped legging up slightly to the dip under your knee makes all the difference if you have calves, as I do (no tall boots EVER fit round my calf!) but since I started wearing them like this, with a pretty tunic top (I am short so they are long enough!), I have had a lot of compliments that my legs look so long, no matter what heel height I wore… as I said, I am only barely 5'2" and wear a US16-18, so that is nice to hear ;))
    So I may continue to wear them like this with tights as the weather cools, hm, have to try that out, especially with the shoes…

  28. lisa

    Thank you for saying that leggings shouldn't be worn as pants. I mostly use them as alterna-tights: something opaque to wear under sweater dresses or to winterize summer dresses which will keep my legs warm and tuck into boots nicely. Or I wear them under shirtdresses with ballet flats. Because a lot of my dresses used to rub against cotton leggings and stick to them, I switched over to the nylon tricot blend ones from American Apparel. They're holding up well so far.

  29. Couture Allure Vintage Fashion

    I love the leopard leggings look! Thanks for the tips!

  30. Kyla

    That outfit with the leopard leggings and kick ass boots may be the most f'n awesome outfit/photo of you ever! You look so BAD ASS!

  31. Laikabear

    Where do you get leggings if you are tall? I am 5'10" and "full length" would be above the ankle on me. Every time I look at Target they don't have them. Since I don't understand fashion seasons, am I going at the wrong time of year? 🙂

    Your "likes dressing comfortably and casually" and "works with animals" is ME! Clearly I need some leggings.

  32. rubybastille

    This is awesome! I agree that they do not qualify as actual pants, although when I was in Ireland I noticed most girls there would beg to differ.

  33. Nifty Girl

    After reading all those tips and comments about leggings, I was inspired to wear leggings-as-pants today. Somehow, I don't have the same ladyparts problem as you–at least in these leggings–and I made sure there were no opacity or pantyline problems… It worked out rather well!

  34. Maggiethecat

    One of the things that intrigued me the most when I first found this blog was the leggings looks. I thought those were something I'd never have any use for, mostly because of my pearish hips and the ladyparts-shaping thing (ack!) but Sal's pointers have made me reconsider them, and now they're definitely in my shopping list for this fall. Don't think I'll be doing cropped leggings though, and at my height I doubt they'll be easy to find anyway, which suits me fine. And I love the animal-print leggings pic! Now that's something I never thought I'd say, but that pic exemplifies the look done right to me… hmm, dare I try it myself?

    For some reason my word verif just cracked me up, btw: anept. As in, seeing so many examples of anept use of leggings turned me off them for years.

  35. liz

    i too absolutely love leggings and they make short summery dresses practical 3/4 seasons. something ive learned is cotton leggings + cotton dress + silky slip = no static [thanks to you!!].

  36. spacegeek

    Wanted to say, I tried the denim-dress as coatlike thing over leggings and a tunic, and my officemates couldn't handle it! Got too many comments about my "trench coat" and it was unfortunate. Oh well, can't win 'em all.

    I like your tips about ankle length and shorter leggings though–I've never tried the shorter ones and think I might do so–S. CA we can get away with more skin year 'round. (But they would be weekend-wear for me in any case.)

  37. Sal

    spacegeek: WHAT?!??!? OK, just tell me who to beat up, and I'm SO on it … how dare they be obnoxious at you for trying out a new look?!?

  38. Emma at Daily Clothes Fix

    I swore off leggings and said I would never wear them. Then I bought a tunic which is indecently short at the back so I bought some. They have turned out to be really useful and I think I might buy a 2nd pair.

    My favourite way of wearing them is either with flats or heels but having a sneaky peek of ankle showing – I like the contrast and it shows they aren't tights.

    And I agree 100% that they are not a substitute for trousers.

    Great post.

  39. Audi

    I love the leggings, and thank you for pointing out that they are NOT pants.

    For cold climates like yours Sal, I think leggings are especially useful in winter, when you can pull a pair of long socks over them (go for thigh high socks if you don't want the tops to show under your skirt). The dual leg layers gives you extra warmth, the leggings keep the socks from falling down while the socks keep the leggings from riding up, and there's still just one layer inside your shoes, so they don't get too tight.

  40. thatgirl

    I love the legging fad… as a petite girl I keep running into these "tunic" tops that are too long on me to be a tunic, but too short to be decent as a dress. Pair with leggings, bingo, instant outfit. Your shoe tips are super helpful though, I haven't been able to get beyond ankle leggings + ballet flats, which I know is a shortening look.

  41. Cindy

    I am considering getting some leggings for winter, but being a "plus-size" woman, I'm not sure about the best way to wear them.
    Any tips for us full-figured gals?

  42. Sal

    Cindy: Since plus-sized women come in all body shapes, I can't really give a simple answer … but since I prefer leggings with above-the-knee tunics on just about all women, if there's a tunic style you like on your figure, start there!

  43. veronica

    Thanks for this! I wanted to wear leggings but didn’t know how. Glad this is up, it’s very usefull!

  44. Lindsay

    Thank you for the pictures and explanation on how to wear leggings. I just bought a pair in Black and have tunics to wear with them that fit just below my hips along with my flat ankle boots. Unfortunately, my Boyfriend doesn’t want me to wear them as he says they look “Trashy” on all Women. Any tips to convince him otherwise?

    • Sal

      Hmm, maybe a longer length of tunic? Or do several layers? Some people just loathe leggings, though. You might not be able to change his mind. My advice would be to style them in a way that YOU love, stick to your guns, and see if he comes around. If not, well, he can love some of your other clothes. (If I may be so bold.)

      • Lindsay

        Thanks Sal. I will try to wear the leggings with the longer Tunics I have and see if that’ll change his mind. 😉

  45. Linda

    I wear leggings with my ballet flats barefooted. I wear them for stlye and comfort barefooted.

  46. Daytime Night Owl

    My only issue with leggings is that I end up wearing a slip too because they stick. I feel like I have to wear 12 layers just so things aren’t sticking.

  47. Natalie Sztern

    I have seen on the market a bandeau out of t-shirt material that one can wear to cover their butt if the t-shirt is not long enough instead of a skirt but I cannot remember the name of them…does anyone know?

    It is a bandeau that can also be worn under a low cut shirt…HELP

  48. Beverly Triplett

    These are by far the most classiest and proper ways I have ever seen leggins worn. MOST women, celebrities included, do NOT know how to wear leggins and are creating major fashion faux pas! Thank you!

  49. allison

    hi i am 20 and 4 years ago when i was 16 i went thru catholic confirmation and per parish requirements had to wear a white,formal,poofy ankle length dress with a veil,elbow length gloves,white knee high leggings and white mary jane shoes.the leggings were supposed to look like we had tights on under our dresses.we also had to wear the required cloth diaper and adult plastic pants and undershirt under the dress to symbolize the purity of our baptisms.the leggings were weird to wear as the elastic was tight fitting around the knees.that is the only time i have ever worn leggings.

  50. Cameron

    Wow, you are so beautiful.

    I especially love the photo of the FULL-LENGTH LEGGINGS WITH SHORT BOOTS on you. So classy!! Leggings are so amazingly comfy and you rock them with amazing style 🙂

  51. Lynda

    I have a very cute dress that comes to middle of my knee and ankle leggings. Is the dress too long?

  52. Tata

    It is so hard for me to find legging that do not ride down. I keep pulling them up and it is very uncomfortable. Can you please tell me what type I should buy?

    • Sally

      Tata, it sounds like you might be buying your leggings too big. Have you tried smaller sizes? Otherwise, look for styles with high spandex content as they tend to be stretchier.