What To Wear With Leggings + 14 Easy 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 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.

If you happen to be in the same boat OR you just have a love of comfy outfits, check out the leggings outfit ideas we’ve rounded up in this blog post.

What To Wear With Leggings

Whether you prefer high-waisted leggings, faux leather styles, or solid black workout leggings, there is one thing that’s for sure – they are a girl’s best friend!

They work for every body type and can be styled so many different ways. 

Here are 10+ of my favorite ways to wear leggings for both casual and dressier looks.

a woman wearing a plaid jacket with black leggings

Shop my faux leather leggings

1. Statement Jacket & Tall 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 tan knee-high boots helps balance it out while creating a chic and classic look. 

Notice that this coat is a longer-than-average length. 

If you don’t know what jacket to wear with leggings follow the same rule that you would with a sweater or sweatshirt: try to cover the bum!

A long coat is typically your best bet.

Trench coats, pea caots, parkas, whichever is more your style – they all work!

Side note – These are my favorite leggings when I’m attempting a more elevated look – Highly recommend!

They are incredible quality but they run small so size up one!

a woman wearing a button down long sleeve top with leggings and a shirt tied around the waist

2. Long Shirt & Denim Jacket

A tunic-length top or oversized shirt is a good choice for a casual look.

This top was long enough to wear with these leggings on its own but tied a denim jacket around my waist because it’s a great way to add some shape. 

Plus, here in NJ we we usually have cooler weather in October, but it is unpredictable.

I tend to go for my solid black faux leather leggings or colorfulkoala leggings the most, but you could easily swap these out for a moto pair to add a little edge.

If you’re into casual wear this outfit is great with a baseball cap and white sneakers for casual days full of soccer, birthday parties, running errands, etc.

A woman sitting in a car wearing leggings, a sports bra, and a zip up hoodie.

3. Sports Bra, Workout Leggings, & Hoodie

Whether you’re actually exercising or just love workout wear, grab a zip-up hoodie to wear over your sports bra and leggings. 

This is one of the easiest ways to create a functional yet easy outfit with a sporty vibe. 

This set is an older one from Fabletics, but you can easily recreate this look with separates from Amazon.

a woman wearing a plaid button up with leggings and knee high boots

4. White Tank Top & Flannel Shirt

When talking specifically about the types of shirts to wear with leggings, don’t leave out a basic tank.

A good white tank top is a wardrobe staple that goes a long way.

I always keep a few longer tops in my closet because I love layering. Plus, they can be worn in many different ways.

This tank top 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 plaid shirts and tank tops are casual, I dressed up the look with a pair of knee-high boots for a little oomph.

This outfit would totally work with ankle booties or sneakers as well.

That’s one of the things I love about classic black leggings – they are SO versatile.

what to wear with leggings

5. Oversized Sweatshirt & Winter Boots

Comfort is key!

Pairing leggings with an oversized sweater or 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 snow boots are the perfect choice for a practical and laid-back look.

woman wearing a black leggings and white sweater outfit

6. 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.

Tip: It’s always a good idea to have a longer layer like an oversized leather jacket to wear over shorter tops when wearing leggings.

This helps to create balance and make the look more polished. 

a woman wearing a vest with leggings, a waffle knit top, and sneakers,

7. 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.

a woman wearing a tan sweater and black leggings

8. Cozy Hoodie & Slip-On Sneakers

Here’s another cute outfit that works for the colder months. 

A cozy hoodie, your favorite sneakers, and a pair of black leggings is a laid-back yet chic look. 

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. 

a woman wearing black leggings with a leopard cardigan

9. Blazer/Cardigan & Ankle Boots

An easy way to dress up a black leggings outfit is to add a blazer or long cardigan.

This one is soft and warm – perfect for cold winter days.

I also have this one and absolutely love it!

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.

a woman wearing a black sweater and black leggings

10. 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 sweater and added the pop of color with my boots.

This is one of my favorite black leggings outfits and it is so simple to recreate!

You can easily go from running errands to date night in this look.

A leggings and sweater outfit can be incredibly chic while still being comfortable and modest. 

If the weather calls for a coat, an oversized bomber jacket would be the perfect addition to this look. 

a woman wearing a tan tunic and black leggings with tan knee high boots

11. A Tunic & Knee-High Boots

A tunic, leggings, and boots outfit is hands-down one of the easiest to put together.

A tunic like this one is a great option because not only is it a tunic but it’s also a sweater, making it a bit more “dressy” so to speak.

Knee-high boots make dressing up any outfit a breeze, so finding a pair you love is an investment worth making.

If I had to choose out of all the shirt styles from above, I’d have to say that a tunic is the best top for leggings.

A smiling woman wearing a tshirt, zip up hoodie, leggings, and sneakers.

11. T-Shirt & Hoodie

Tanks and tees in solid colors are more my jam, but if you prefer a graphic t-shirt in bright colors, those work, too!

Throw on your preferred t-shirt and layer it with an oversized zip-up hoodie and coordinating sneakers for a cozy yet stylish outfit. 

A woman sitting on steps wearing a colorblock sweater, leggings, and chunky chelsea boots

12. Color Block Sweater & Chelsea Boots

For an edgier look, opt for a pair of chunky Chelsea boots

These are my go-to and they are available in several colors. 

While the sweater is on the shorter side, you could easily create a layered look with a long jacket. 

Bonus points for this whole look being available on Amazon!

A smiling woman wearing a long shacket, black leggings, and combat boots.

13. Shacket & Combat Boots

For an extra layer of warmth, consider adding a long shacket to your ensemble. 

As mentioned earlier, in NJ our fall weather is always questioable. 

It could be 45 degrees or 82, we just never know. 

That’s why I love the idea of adding a shacket over my top. 

Not to mention it’s a comfortable yet fashionable look!

A smiling woman wearing a tunic top, black leggings, and black boots.

14. Tunic & Combat Boots

This is my all-time favorite tunic and leggings combo.

This top is extra long, has a wide body but fitted sleeves, and comes in a ton of colors.

Paired with Boots its offers an edgier look while still being comfortable and casual enough for everyday.

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.

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 by 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.

Best Shirts 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. Tunic
  2. Oversized hoodie
  3. Long tops (tanks, tees, sweaters, etc.)
  4. Flannel
  5. Button-down shirt (like a chambray shirt)
  6. Vest
  7. Oversized Cardigan

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.

You shouldn’t feel stressed when trying to figure out what to wear over leggings or how to style them.

Take a quick look in your closet and I’ll bet you have most of these items already!

FAQS

Are leggings in style for 2023?

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.

Can you wear a dress with leggings and boots?

Pairing leggings underneath a dress that you feel is too short is a perfect idea.

Additionally, if the weather is just too cold for a dress, leggings are the perfect way to wear your dress without being too cold. 

Finish the look with the right shoes like a pair of over-the-knee boots, booties, or mules. 

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

This depends on the style you prefer. 

These are my go-to leggings in a cotton blend style for ultra casual outfits.

SPANX faux leather leggings are the best leggings for a more elevated look.

This is what I wear for looks that are a little bit more polished. 

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.

These leggings 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.

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.

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 or ballet flats, a tunic/tank, and a blazer could totally work for the office.

Conclusion

Leggings are one of the most versatile piees of clothing a girl can have in her closet. 

And while fashion trends come and go, leggings are one garment that has never gone completely out of style. 

There are so many different outfits you can create with them, plus they’re comfortable and generally quite affordable. 

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2 Comments

  1. 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.

    1. 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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