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What to Wear With Leggings + 7 Style Tips

what to wear with leggings, how to wear leggings, 20+ outfit ideas with black leggings

You GUYS! I’m pretty pumped to FINALLY be pulling together all my thoughts to answer all your questions (literally, ALL) regarding what to wear with leggings, how to wear leggings and ALL THINGS acceptable-leggings-outfits! I feel like I’ve been wanting to put this blog post together for so long and just haven’t had the motivation. But after a few of you guys sent me personal emails with specific questions, it was JUST the fire I needed to get me moving on finishing this post! So let’s talk ALL about what to wear with leggings, shall we?!

I know there’s a lot of debate out there regarding legging’s legitimacy – they’re quite the controversial item!  And although I do agree with many of the critic’s arguments, I’m on team leggings 100% and here to argue that leggings (black, specifically) can also be a stylish essential for your everyday wardrobe. Further, there’s an art to making the notorious stretchy bottoms look chic in your day-to-day rather than just your sweaty/workout life.

7 Style Tips on How To Wear Leggings

Things To Keep in Mind When Considering What to Wear With Leggings:

  1. Make sure your leggings are opaque and made of a thick material.
  2. Pair with accessories to elevate your leggings outfit.
  3. Wear leggings that go to your ankles rather than cropped leggings unless you’re going for the athleisure look in which case I suppose you’d want your leggings to be cropped.
  4. Be sure to wear the right kind of underwear (aka make sure you can’t see panty lines!).
  5. Contrast tight leggings with an oversized, loose-fitting top or cardigan to balance out the look.
  6. Make sure whatever you wear on top covers your rear end or is long enough.
  7. Remember, leggings are not pants and shouldn’t be worn to substitute pants.
  8. Play up layering when wearing leggings to add more dimension and “umph” to your outfit making it more interesting.

What To Wear With Leggings

In order to truly answer the question “what to wear with leggings?,” I feel like I’ve GOT to actually give some evidence other than explanations and tips etc. In other words, I wanted to show y’all some outfit examples illustrating a few ways I’ve worn leggings in the past.

After looking through all my old outfits with leggings in order to put together this post, I noticed a few common denominators. Almost all of my outfits follow a similar formula: Longer Tunic or Shirt + Layering and/or Accessories + Knee-High Boots. As you scroll through the outfits, note how each look incorporates this easy formula in some way or another. I’m going to bring you through 3 different TYPES of outfits that work with leggings.

what to wear with leggings - plaid tunic button up and riding boots for a casual, laid back leggings outfit

1. With a Plaid Tunic Button Up

If it’s long enough to cover your rear, I’d argue that you’re safe wearing your fave plaid shirt with leggings. If you’re going for a super cozy, laid-back look for traveling or running errands around town throw on your favorite sneakers for a casual, cute look. But if you’re looking to elevate the look, throw on accessories and riding boots or maybe even a baseball cap to complete the look. Regardless of how you style it, I’d say that an oversized flannel or plaid paired with leggings is going to give you an all around casual, laid-back (but cute!) look.

what to wear with leggings: oversized chambray shirt, layred open cardigan and tall leather riding boots

2. Oversized Chambray Shirt

Or if you’ve got an oversized (tunic-length) chambray, you can put together a similar look. In this look above, I threw on a neutral cardigan over my denim shirt and leggings, adding an additional layer to give the outfit more dimension and make it a bit more interesting. But again, you’ll see that I’m wearing my Frye boots to distract from the fact that I’m not wearing pants (ha!) and get away with wearing leggings!

what to wear with leggings - fall outfit, leggings outfit with plaid shirt, tunic plaid shirt with leggings, tory burch junction riding boots, basebal cap, white hanes tee, comfy black leggings outfit for fall

3. Paired With an Unbuttoned Plaid Shirt

Instead of wearing the plaid shirt buttoned-up like in the previous two outfits, opt to wear it unbuttoned with a longer white tee or tunic underneath for an EVEN more laid back look. In this case, I added my Patagonia better sweater vest to add more of a layered look to my casual leggings and riding boots ensemble.

Brighton The Day wearing a long cardigan with leggings and riding boots, valentino bag, marled cardigan

4. Oversized Cardigans & Sweaters

Similar to wearing leggings with an oversized plaid or chambray shirt, you can wear a longer cardigan or oversized sweater. Pairing an oversized knit with your leggings is a great opportunity to use juxtaposition to your advantage, contrasting the tightness of the leggings with a loose-fitting, oversized (maybe even chunky!) cardigan or cozy sweater!

I remember I wore this look (above) to run a few errands last Fall and then to my small group bible study. The tall, leather boots coupled with the cardigan (layers!) elevate the look, bringing it from sloppy to pulled together and cute.

airport outfit, lake tahoe, comfy chic, oversized cardigan, plaid scarf

5. An Oversized Cardigan

I’m actually NOT wearing leggings in this outfit, BUT I wanted to include it to show that if the underneath sweater layer was a little longer, then this look would be a cute leggings outfit! Except instead of the booties, I’d probably wear my Frye boots or some other knee-high boot option!

This outfit is from my trip to Lake Tahoe with The Ritz Carlton – Check Out the full Lake Tahoe Travel Guide

brightonkeller instagram january tunic sweater, leggings, tall brown boots, waterfall open front vest, gold pendant necklace winter outfit

6. Tunic-Length Sweater & Waterfall-front Vest

And lastly, for the outfit above, I think what makes it work is the fact that (a) the sweater is tunic length (a given!), (b) the sweater and the open-front vest are different textures (ribbed sweater vs. smooth knit vest) and lastly the fact that (c) the leather boots elevate the entire outfit. I think this might be one of my absolute favorite leggings looks I’ve ever put together – the color palette is what makes me love it! And the fact that it’s got such a cozy, cute feel to it!

7. Wear leggings with A Tunic Tee  & Layers

Similar to wearing leggings with an oversized sweater or cardigan, you can also wear them with longer tees and tunics. This is probably the most common “leggings outfit” – according to what I’ve seen on Pinterest at least. I’ve also seen people wear leggings under dresses, which can be cute too! (although I think I’m too short to wear this combo – I prefer to wear tights in that case). I’ve put together a few example of wearing leggings with tunic tees for y’all below.

cargo jacket + skinny jeans + riding boots + striped tee

8. Striped tunic tee & utility jacket

In this outfit I wanted to wear my striped tunic tee with my utility jacket and riding boots because I love the way these 3 items look together. I could have easily worn my blue jeans but I felt like it would be too many colors going on, plus I wanted something a little more laid-back and comfortable – and leggings were just the answer for completing this look. Plus, the taller riding boots and the longer tunic lave only a little bit of room for my leggings to show anyway so I felt like wearing a pant (like a blue jean) would have been a bit bulky.

how to wear leggings - wear leggings on a rainy day, rain day outfit with hunter boots, hoodie, puffer vest, baseball cap, black hunter boots

9. Cozy Hoodie, puffer vest & Hunter Boots

If it’s chilly outside and I’m not wearing my blue jeans with my hunter boots, then odds are I’m wearing leggings and something oversized on top. I love a good hunter boots and leggings combo for a rainy day – especially when I don’t need to be dressed up for anything (like just running around town like I did in this post).

what to wear with leggings, leggings travel outfit, comfy casual outfit leggings and sneakers, denim jacket, babeball cap, celine bag

10. Tunic-Tee, Denim Jacket & Blanket Scarf

Again in this outfit above, I’m wearing my leggings with a tunic-length tee and piled on a few layers to add a little more dimension and interest to this laid-back, casual get up. This would (obviously) be an idea look for traveling or running around town when it’s chilly out!

What shoes can you wear with leggings?

First, I want to say that this is a difficult question to answer because you could go a lot of different ways with the answer. Plus, it’s hard to answer something like this in general terms because there will always be exceptions to generalities or best practice suggestions. But I’ll do my best to answer in the most informative way for those of you curious!

Wear Leggings with Taller Boots and/or Sneakers

For the most part, I think taller boots look best because they distract from the fact that you’re wearing leggings. But again, there are of course circumstances where you can make other types of (non tall) shoes work! I’ve noticed celebrities are notorious for wearing leggings (with loafers or other chic shoes) while traveling and they always make them look chic!

fall outfit idea, duck boots, buffalo plaid puffer vest, stripe turtleneck, fall layers

Same with this look – it’s more of a comfy/lounge look but not really an “actual” outfit. Plus, now that I look at it, I think my shirt is too short to be wearing with leggings anyway (ha!)

What about leggings and sneakers?

Sneakers and leggings are a great combo if you’re going for a super athleisure or laid-back casual/cool look for lounging around, running around town, or even traveling. Here is an example of leggings with a tunic-length shirt and layers worn with sneakers:

what to wear with leggings, leggings travel outfit, comfy casual outfit leggings and sneakers, denim jacket, babeball cap, celine bag

What about leggings and pumps?

In the case of dressing up your leggings or wearing them with pumps, I’m just going to go ahead and say DON’T (unless you’re wearing faux leather leggings – in which case is totally FINE! like I did in this outfit!). You can just substitute your leggings with tight black pants and not have to worry about it. I really don’t see where you’d need to wear leggings in a dressier-looking outfit and couldn’t wear black pants instead.

black leggings outfit with grey tunic, scarf, brown booties 11

Can you wear leggings with ankle booties?

I’ve changed my opinion and I now say YES! I used to think that it was hard to pull off wearing leggings with ankle booties. Wait actually, I used to say you couldn’t wear the two together actually. But I have since changed my mind! I think the key is that you need to show a little bit of ankle in order to pull it off? I can’t quite articular WHY this is the case, but I THINK this is what makes the difference! This outfit is originally form this blog post!


WHEW! OK that about sums up EVERYTHING I’ve got in my brain and years of experience when it comes to how to BEST wear leggings! I hope I’ve given you plenty of inspiration on what to wear with leggings so that you can find any and every excuse to style them yourselves. After all, they’re by far the most comfortable things out there!

What did you think?!

Did you find this article helpful?! Did I miss anything? Comment below with your thoughts, friends!

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  • Reply
    December 27, 2017 at 11:25 am

    I am 75 years old and have just taken a like to leggings this past year. My aunt had been wearing Fadeded Glory
    Via Walmart for years-she would buy 6 or 7 pairs at a time. She was a real close horse even at 90 years when she
    passed away. I ‘m so glad I came upon your sight, which is so informative. For Christmas I even bought myself
    some tunic tops and I think my husband even liked them. I think all your outfits were very stylish. Hot dog!


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  • Reply
    November 4, 2017 at 12:38 pm

    Thank you for the ideas! I’m in my fifties, and although my generation thinks of themselves as still kids…the new thirties…it’s a little difficult trying to get away with wearing leggings. I go abroad a lot, and the tennis shoe and legging idea works very well! I pair them with a dress jacket, usually a wool riding jacket..longer, and a great scarf. Thank you for throwing in the Hunter boots. I wear mine, my Bean boots and regular leather tall boots a lot, and with leggings, I think it gives a younger look. When I want, I put my half chaps over my Bean or booties for a tall look. Thank you for the ideas, and putting into words, the feeling of reserve I’ve had, when wanting to wear leggings. Sometimes I’m not sure! You made it right!

  • Reply
    January 10, 2017 at 12:37 pm

    I noticed you mostly wear brown boots with your black leggings. How do you feel about black boots over black leggings? More specifically, black OTK boots?

    • Reply
      November 4, 2017 at 12:39 pm

      I think black with black is slimming and pretty!

  • Reply
    January 9, 2017 at 5:44 pm

    I loved the post especially since you shared multiple ways how to wear it (most blogs just have like one or two options). I personally am a big fan of black lululemon leggins. I love wearing them with short casual dresses or with a long top that has a wide lace seam at the bottom that lengthens it optically. Also i need to walk a lot (Hello, Europe) so sneakers are usually my go-to shoe choice.

  • Reply
    Haley Henderson
    December 30, 2016 at 2:39 pm

    Found this through your Best of 2016 post, and it is truly the BEST blog post I’ve read maybe ever! Thank you so, so much for putting this together. I am in law school, and very frequently find myself in the fashion rut of wanting to be comfy (long nights in the library), but needing to look put together. I will definitely be referencing this post all semester long for inspiration :) Happy New Year!

  • Reply
    Mrs DailyGrindFree
    December 20, 2016 at 7:55 pm

    Great post! I’ve had trouble trying to style them but you’ve given some great tips:) Have you ever tried Lysee? Wow, talk about sucking you in yet still feeling super comfy!

  • Reply
    December 4, 2016 at 5:49 pm

    Cute! Where can I buy the striped tunic in the set with the utility jacket? I clicked the link and Nordstrom is sold out. 😟

  • Reply
    November 30, 2016 at 10:26 am

    This was so helpful to me! I just want to buy all these pieces and copy your outfits just for the ease of it! BTW, it’s very helpful that so many of your pieces are from Nordstrom- makes it easy to shop! I already put two things in my cart. It’s nice to see a woman who is “not so tall” do leggings so well!!! Thank you!!!

  • Reply
    November 24, 2016 at 8:13 pm

    I LOVE all of your suggestions! I’m a huge fan of leggings and take advantage of any opportunity to wear them, so this is perfect! I have 2 questions. I really like the Halogen Open front cardigan and the Patagonia vest. I noticed the Halogen cardigan is OS- do you still like the way it fit you? I read some reviews and people weren’t crazy about the OS because it was too big. I’m 5’6 and 120 pounds so I don’t know if it would be way too big or not. As for the Patagonia vest, what size did you get? I’m typically between an XS and a S, but don’t know if it runs big, TTS, or small.

    Thanks in advance for your feedback :) Happy Thanksgiving!

    • Reply
      Brighton Keller
      November 25, 2016 at 3:44 pm

      Hey girl!! Yes it’s very oversized but I LOVE it! I feel like I throw it on all the time! In fact i wore it on a date last week! I got a size XS in the Patagonia vest! hope that helps!

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    Meals in Heels MKT
    November 21, 2016 at 8:43 am

    Love this post!! All of these are such great looks


  • Reply
    Niamh Marie
    November 20, 2016 at 9:29 pm

    I totally appreciate this post and all the ideas of how to wear leggings and still look cute and polished :) My favorite combo is the sweater/vest/hunter boots combo. Totally a cold weather staple for me!

  • Reply
    Emily Hildreth
    November 17, 2016 at 6:18 pm

    What is your favorite brand of leggings/what kind do you wear most? I want them to be thick without being “athletic” looking at all! Thanks Brighton, I love your posts!

    • Reply
      Brighton Keller
      November 18, 2016 at 10:12 am

      wait I feel so silly – did I not recommend any in this post lol? I think I need to make that more clear bc that would for sure be my question at the end of an article all about leggings too! I personally love these [[ ]] because they’re thicker and suck you ALL in! I also love that they’re high-waisted, which I think is a MUST bc it’s just comfy and “Feels” better! I don’t recommend the “HUE” ones (although they’re a great brand) because I think they’re too thin and don’t feel as secure – if that makes sense!

      Also, I love the tights & leggings (!) by SPANX as well! Talk about SUCK ya in! They’re worth a shot too!! here’s the link:

  • Reply
    Indi Stilling
    November 16, 2016 at 2:11 pm

    I love this post, great tips!

    • Reply
      Brighton Keller
      November 17, 2016 at 1:28 pm

      yay! Thanks so much! It was fun to put together!

  • Reply
    Amy Michelle
    November 15, 2016 at 8:03 pm

    I am definitely team leggings! I love how you were able to put together these tips and examples of what to wear with them!


  • Reply
    Charmaine Ng
    November 15, 2016 at 3:37 pm

    I LOVE leggings! They’re my favourite clothing items and these are cute new ways to wear them!
    – Charmaine

  • Reply
    Davida Janae
    November 15, 2016 at 1:24 pm

    Great tips as usual Brighton!!! You have great legs by the way!

    • Reply
      Brighton Keller
      November 18, 2016 at 10:12 am

      aww thanks so much!! That’s actually my most self-conscious area (we all have one!) so that means a lot!

  • Reply
    November 15, 2016 at 12:10 pm

    I feel like this blog post needs to be a PSA of sorts! I think we have seen ones wear leggings and it wasn’t quite right. ALL of your outfits were just perfect!

    • Reply
      Brighton Keller
      November 18, 2016 at 10:13 am

      I just LOLd reading this comment! Thanks so much!!

  • Reply
    Abigail @ Belle of the Brier
    November 15, 2016 at 12:08 pm

    As someone who is obsessed with leggings, I LOVED this post! Such helpful info! Pinning it for future reference for sure!

  • Reply
    Rach Martin
    November 15, 2016 at 10:51 am

    I love leggings but I try so hard not to wear them out of the house unless I’m doing something casual! The second I start wearing them more often, I tend to forget what jeans are all together, haha! Love these tips (especially the underwear one!).

    Rachel /

    • Reply
      Brighton Keller
      November 18, 2016 at 10:15 am

      omg girl me too! Same with my FRAT tees…there’s just so thick and comfy – I could legit live in those tees and leggings for LIFE. hope you have a great weekend, Rach!

  • Reply
    From Aliona With Love
    November 15, 2016 at 10:37 am

    Loved reading this. Please check out my latest winter trend alert!

    Kisses xo | From Aliona With Love

    Instagram @alionawithlove

    Twitter @alionawithlove

  • Reply
    Courtney Gwin
    November 15, 2016 at 9:04 am

    I have been having issues finding cute shoes to wear with leggings recently so this post was perfect! Love your blog!

    • Reply
      Brighton Keller
      November 18, 2016 at 10:14 am

      aww I’m so glad to hear it!! Thanks so much! hopefully you got some outfit inspiration and have been able to put some looks together yourself! hope you have a lovely weekend, Courtney!

  • Reply
    Jess @ Just Jess
    November 15, 2016 at 8:40 am

    I love all of your outfits. I love leggings for traveling and running to the store but that’s about the only time I wear them. Jess at Just Jess

    • Reply
      Brighton Keller
      November 18, 2016 at 10:14 am

      they’re so comfy! I don’t blame you :) thanks for stopping by, Jess!

  • Reply
    Leeann Bienfang
    November 15, 2016 at 8:27 am

    Love these outfits! Thanks for sharing :)

  • Reply
    November 15, 2016 at 6:50 am

    I’m pretty much in agreement with you here. I’m all for leggings too as long as there is nothing showing that shouldn’t be! I have an obsession with Lush tunics and I love wearing them with leggings. I have actually them with booties too -although it was a monochromatic look with black. I felt like it worked, but it’s not a look I do often. Thanks for the great tips!

    • Reply
      Brighton Keller
      November 18, 2016 at 10:14 am

      hehe glad we’re on the same page!! And omg yeah, I’m obsessed with them too! I actually did an entire post on WHY I’m so in love with them :)

    • Reply
      August 18, 2017 at 12:34 pm

      I love that look and it’s one of my fav seasonal outfits, I wear leggings nearly all Fall and Winter. I have worn leather bootie Boots with leggings, however when doing that style I really dress it up with accessories and make the whole look very “Classy” The question I always get is…..”Where did you get that”? As if I bought the whole outfit off the maniquin, silly.
      I think some just don’t know how or what to wear with leggings. As mentioned, please keep those backsides covered up.
      I love the monochrome – Black leggings, long black sweater, and waistline leather jacket, I add a scarf in the dark grey family and tie in my eye makeup.
      Leggings are wonderful, and can make you look and feel beautiful, if your not sure how to wear them, look for a blog or someone that knows. The rule to live by is cover that backside….Enjoy Ladies and thank you for sharing…..Happy Day, Yakti ¥

  • Reply
    November 15, 2016 at 6:30 am

    I’m 100% with team leggings! They’re just too comfortable! I love your ideas on how to wear them!

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