What To Wear With Leggings + 10 Outfit Ideas

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Leggings are my jam. Why? Because although leggings aren’t technically pants, you can still style them in a way that makes them appropriate for almost anywhere you go.


I don’t know about you, but I’m SO much more comfortable wearing leggings than jeans. That’s why I’m super excited to be sharing this guide on what to wear with leggings plus 10 easy-to-recreate legging outfits to help along the way.


Since NJ is chilly and/or freezing about half the year, comfort is a must for me. I love getting dressed up every now and then but realistically leggings are much more practical. Who wants to be trucking through the snow in jeans and booties? Not me.


As I looked back through all my photos of legging outfits I realized a pattern. Almost all outfits had the same 5 key details which include:


6 Tips For Styling Leggings

1.) Cover the butt! Leggings look much more appropriate/put together when you pair them with a longer top.

2.) Opt for leggings with a thicker fabric. Leggings that are very thin or partially see-through definitely look cheaper and make the overall outfit look less put together.

3.) Layer, layer, layer. Layering up top takes away from the fact that you’re wearing leggings (like a tank top with an open flannel or a long tank top under a sweater).

4.) Experiment with different types of shoes. Don’t be afraid to pair leggings with booties. Sure, leggings with sneakers are great, but if you want to elevate your outfit don’t be scared to play with different shoes.

5.) Wear proper undergarments. Panty-lines aren’t generally a part of a well-thought-out outfit. Wearing the proper undergarments can easily take your leggings outfit from trashy to classy.


6.) Wear the right length. This is especially important if you’re pairing leggings with booties or sneakers.


What are Leggings?

Before we dive into what to wear with leggings, let’s first talk about the exact kind of leggings I’m referring to. This post is NOT sharing what to wear with workout leggings. It is specifically for leggings that you plan to wear as part of an everyday outfit.


Generally speaking, leggings that you plan to wear as part of an outfit are made of thicker fabric, are NOT opaque, and often feature a quality texture like faux leather.


Now that we know the exact leggings we’re referring to, let’s take a look at some of the simple ways you can create chic leggings outfits.


What To Wear With Leggings

plaid jacket with black leggings

1. Statement Jacket & Knee-High Boots

Adding a statement jacket to almost any leggings outfit can instantly change the entire look. All I’m wearing underneath this coat is a simple black turtleneck. A pair of classic, tan knee-high boots helps balance out the outfit while keeping it classy yet comfortable.


Notice that this coat is a longer than average length. Follow the same rule with coats when pairing with leggings that you would with a sweater or sweatshirt, try to cover the bum!


Shop The Look


what to wear with leggings

2.) Thermal Shirt & Denim Jacket

This top was long enough to wear with these leggings on its own, but I added the denim jacket tied around my waist for a little shape. Plus, October weather in NJ is so unpredictable. I tend to go for my solid black faux leather leggings the most but you could easily swap these out for a moto pair to add a little edge.


If you’re into the casual/sporty look this outfit is great with a baseball cap for weekends full of soccer, birthday parties, running errands, etc.


Shop The Look


what to wear with leggings

3.) White Tank Top & Flannel

A good white tank top goes a long way. I always keep a few in my closet because I love layering.  Plus, they can be worn in many different ways. This one is great because it’s a longer length (covers the bum) and it has a bit of stretch to it.


*For reference: I’m 5’4″ and have a long torso.


Although the flannel and tank are casual, I dressed up the look with a pair of knee-high boots for a little oomph. This outfit would totally work with sneakers, too. That’s one of the things I love about leggings – they are SO versatile.


Shop The Look


what to wear with leggings

4.) Oversized Sweatshirt & Winter Boots

Comfort is key! Pairing leggings with an oversized sweatshirt is an easy way to look great while staying warm. NJ gets FREEZING in the winter and we often get quite a bit of snow so I threw on my Sorel boots with this outfit to stay warm and not break my ass falling in the snow.


Shop The Look


black leggings and white sweater outfit

5.) Cowl-Neck Sweater & Fur Boots

If you can’t tell by now, I don’t believe that leggings can only be worn with sneakers. You can easily elevate your leggings outfit with a statement pair of boots like the ones above. I kept the top simple with a classic ribbed cowl-neck sweater and let the boots do the talking.


Side note – I can’t rave enough about these boots. They are SO COMFY and go with both leggings and jeans!


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what to wear with leggings

6.) Long Sleeve Tee, Vest, & Sneakers

As you can see by the cute little bundle in the back, I’m a mom. Most days of the week I’m chasing children around all day, which is why my outfits tend to look like this most of the time.


Wearing sneakers doesn’t have to look sloppy. Throw on a nice clean pair with a comfortable t-shirt and an unzipped vest for a sporty yet sleek look.


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what to wear with leggings

7.) Cozy Hoodie & Slip-On Sneakers

Another practical way for moms to wear leggings is with a cozy hoodie and some easy throw-on-and-go sneakers. Accessorize with your favorite bag and a great pair of sunnies for a polished look that is still easy to run around in all day.


I usually stick to oversized hoodies but this circle hem sweater-hoodie works, too. If you prefer more of a sweater look than a sweatshirt, check out Express, Aerie, and H&M. They tend to carry styles like the one I’m wearing above.


Shop The Look


what to wear with leggings

8.) Cardigan/Blazer & Booties

An easy way to dress up a casual leggings outfit is to add a chic cardigan. This one is soft and warm – perfect for cold winter days. I paired it with a basic black tee to let the print of the cardigan stand out. The black on black also helps to create a nice lean look from top to bottom.


I don’t typically wear booties with leggings but I thought it paired perfectly with this combo! Again, I polished off the look with a statement bag and a pair of my favorite sunglasses.


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what to wear with leggings

9.) Go Monochromatic

There’s something about a black-on-black outfit with a pop of color that just gets me every time. I LOVE tan and black together so I threw on this long black sweater and added the pop of color with my boots.


This look is so simple yet can easily go from running errands to date night.


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what to wear with leggings

10.) A Tunic & Knee-High Boots

A tunic and leggings outfit is hands-down one of the easiest to put together. This tunic, in particular, works well because not only is it a tunic but it’s also a sweater, making it a bit more “dressy” so to speak.


Shop The Look


Knee-high boots make dressing up any outfit a breeze, so finding a pair you love is an investment worth making. Here are a few below with great reviews.


What shoes can you wear with leggings?

Obviously, as you can tell from this post, I don’t think there’s one specific answer to this question. Typically, I don’t find booties to go well with most of my leggings outfits. However, there are exceptions – see number 8 above!


Sneakers and knee-high boots seem to be the easiest to pair with leggings, but if you have another preference, give it a try! You never know until you put it on and see how it looks.


Pumps and/or a blazer can elevate your leggings outfit and turn it from a casual day look to a date night look or office attire. I don’t work in an office setting so I don’t wear blazers often, but a pair of quality leggings with pumps, a tunic/tank, and a blazer could totally work for the office.


Take a look at this outfit below for office inspiration.

Blazer | Leggings | Pumps


Notice her tank top underneath the blazer isn’t long enough to cover her front/back but it still works because the blazer balances it out.


Mules also work with leggings and tend to look best with a print like leopard or snakeskin, or with a contrasting color.


Here are some affordable options with great reviews.

Are leggings in style for 2020?

HECK YES! Leggings are totally in style, especially because there are so many different ways you can wear them. Take a look through your closet and I bet you’ll be surprised at how many different legging outfits you can put together with what you already have on hand.

How NOT to wear leggings

Unless you’re intentionally pairing a crop top with leggings for a specific look, I recommend staying away from shirts that don’t cover your butt. Additionally, tops that are too tight are another no-go.

Leggings tend to be fitted around the waist so you don’t want to have the line of your leggings accentuated but a top that is too tight. A looser, flowy top also helps to balance out the tightness of leggings.


Another no-no is wearing leggings with visible underwear lines. When wearing leggings you should always opt for undergarments that are easy to conceal.


What is the best pair of leggings (quality, comfort, style)?

Hands down, without a question, no argument here – SPANX. If you didn’t notice from the pictures above, I’m wearing the same pair of leggings in every. single. photo. Spanx faux leather leggings are nothing short of incredible.


I do find Spanx leggings to run small. I am a size 4 or 27 in almost every bottom I own but in Spanx, I size up to a medium and they are PERFECT. They are totally an investment and I’ll admit it took me a while to take the leap, but holy cow am I glad I did. I promise you won’t regret it.


The quality of Spanx leggings is the best I’ve ever tried and they don’t look like the typical bum-around legging. Dress them up, dress them down, do whatever the heck you want because YOU CAN. I can’t rave about them enough.


Spanx does have a wide variety of leggings but the ones I get the most use out of (and believe you will, too) are the plain faux leather leggings.



Tops To Wear With Leggings

As mentioned above, the best tops to wear with leggings are those that cover your behind and help to balance out the “tightness” of your leggings. However, there are many different styles that fit this bill! Here are the best style tops to wear with leggings:


  1. Tunics
  2. Oversized hoodies
  3. Long tank tops
  4. Flannels
  5. Chambray shirts
  6. Long sweaters
  7. Long t-shirts
  8. Vests
  9. Cardigans


Where to find quality leggings

By now you know that Spanx is my go-to. However, there are several other brands/retailers that offer high-quality black leggings as well. Whether you’re looking for leggings for everyday wear or a pair that’s suitable for the office, this list is a great starting point.


  1. Banana Republic – As a retailer that keeps the working girl in mind, it’s leggings are on the classic/preppy side and often have incredible reviews.
  2. Express At Express you’ll find leggings that feature the latest and hottest trends such as vegan faux leather, sequins, velvet, etc. If you’re looking to add a little edge to your leggings outfit, Express is the way to go.
  3. Loft – If ponte leggings and cozy fleece options are more your style, Loft is the way to go.
  4. J. Crew – J Crew leggings are definitely on the pricier side but also offer the most options with 6 different fits, all featuring high-quality fabrics. Side note – J. Crew frequently has HUGE sales.


That’s it for this “What To Wear With Leggings” post. I hope you found some inspiration here to get you started with your leggings outfits!


Be sure to follow me on Instagram where I share daily outfit inspo, free workouts, and weekly sales!


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Lauren is a wife, mom of 3, and personal trainer with a passion for fitness, fashion, and blogging. She shares affordable fashion finds, fitness tips, and helps you learn how to make money with YOUR blog!


  1. Cristina Soarés
    May 5, 2021 / 12:46 pm

    LOVE your style options with leggings! I’m 35 (and a sz 10); so, it often seems difficult -on the younger side of middle age- to try to not look either like I’m trying to be a sz 0 20 y.o. (or, lol, on the opposite extreme: like a slob letting myself go!). I have a pear figure (which I’m completely proud of, thank you!) and, think leggings accentuate it better than trying to hide it by wearing bulky/drapey clothes which make my sides only look heavier. My go-to pairings with leggings are (for formal-casual): black knit ones with a satin cami shell top and a blazer or velour tuxedo/dinner-type jacket over that. For everything else: ultra fleece hoodies or long cardigans. Don’t get me started on “jeggings” though! I CANNOT STAND THEM. I love the vintage real denim of the ’70s and ’80s, in that case.

    • Lauren
      June 14, 2021 / 2:09 pm

      haha! I love denim too. I love blazers as well, but I have big arms and broad shoulders so finding ones that fit me well throughout the midsection as well as the shoulders/arms is soooo hard for me!!! Blazers instantly dress up any outfit!

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