How To Wear - November 15, 2016

What to Wear With Leggings + 7 Style Tips

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

I’m always looking for an excuse to put together an outfit with leggings. I practically live in mine! So I’m particularly stocked to be putting together this comprehensive guide on what to wear with leggings.

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 I’m here to argue that leggings (black, specifically) can also be a stylish essential for your everyday wardrobe. There’s an art to pulling off a cute leggings outfit in your day-to-day life rather than just your sweaty/workout life.

8 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 longer leggings rather than cropped; it gives you a more “finished” look
  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 showcase some outfits illustrating a few ways I’ve worn leggings.

After looking through all my old outfits with leggings, 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.

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, throw on your favorite sneakers for a casual, cute look. But if you’re looking to elevate the look, add accessories and riding boots.

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 examples 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 from 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!