What to Wear With Leggings & 20 Style Tips on How to Wear Them

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Leggings Style Guide

Leggings are one of the most comfortable items you can wear, but this go-to wardrobe staple has its detractors. It can be challenging to decipher at times how to wear leggings and what to wear with leggings. I love leggings, and I’m here to help you style this much-loved staple into stylish leggings outfits for fall, winter, and spring.

Leggings have been around for centuries; they have been made of various materials and used for different purposes. They have been adapted, updated, and transformed into a closet staple and are still holding steady. They may change material and colors from season to season, but you can wear classic black leggings every year.

So if you have been hesitant to try leggings, criticized for wearing leggings, or want to update your style for cooler weather, make sure you read this entire post. I’ll show you what to wear with leggings so you can put together cute leggings outfits that will take you almost anywhere you want to go.

What Are Leggings?

Before we get into what to wear with leggings, I want to clarify what I mean by leggings. I am not referring to workout leggings that you’re trying to pass off as everyday casual wear. The leggings I am talking about in this style guide are black, sometimes black leather, or dark gray leggings that end at the ankle. These leggings are made from thicker fabric and do not extend to cover your feet.

In other blog posts, leggings are also sometimes confused with tights. Tights go from your waist to your toes and come in absolute opaque, opaque, and sheer. Tights are also more commonly worn in crazy colors, prints, and textures.

Shopping for Women’s Leggings

When shopping for leggings look for dressy leggings made of thick material, you don’t want anything that is see-through. Make sure they are soft, so they are comfortable to wear. They need to be form-fitting, so they flatter your legs and hold you together. If you purchase leggings that are too thin, you run the risk of feeling unsupported, and in turn, you will feel very uncomfortable.

Lastly, a great legging is versatile and can be worn to work, a dressy night out, or for a casual weekend with a long cardigan or tunic. Good quality leggings might cost more and you might see it as an investment but they are worth it if they fit you correctly and you can wear them for various occasions throughout the year.

Most of the time I prefer black leggings, a black legging is what I wear most of the time and what I would invest in adding to my wardrobe. Don’t drop more than $100 on leggings that you don’t know how often you will wear or that are not classic black. They are not worth it.

I own a pair of black leggings that I love, and they were only $50 from LOFT. They are the Leggings In Ponte, as of writing this they have 179 reviews with an average of 4.7 stars! Worth the price! If you want to try on a variety of leggings in one stop, I recommend going to Nordstrom.

My last shopping tip, make sure you try them on! I know it, ugh! I have to go to the store, select a handful of leggings, go to the fitting room, try each of them on! So much work, blah, blah, blah. I hear it all the time, I’ll just buy them and try them on at home, and if I don’t like them I’ll return them. NO! That never happens, you end up wasting money and with no black leggings. Try them on at the store, ask for shopping assistance! The Nordstrom department assistants are more than happy to help you put together outfits. They help you see what works and what doesn’t and what to wear with leggings.

How to Wear Leggings

I want to review some of the dos when it comes to wearing leggings. These style tips are general tips to follow. Sometimes when the outfit looks very nice, these style tips can be broken. (As you’ll see in the winter leggings outfits example below). Use these as guidelines; they are meant to help you decide on the types of leggings to wear, and how to wear them, so you look and feel your best.

Again, these are style tips that I use because I always want to look stylish you don’t HAVE to follow them, but it’s advisable.

1. DO wear proper-fitting leggings
2. DO stick to dark-colored leggings.
3. DO stick to solid colors.
4. DO keep it classy, not sexy—unless you are going for sexy, of course. (Read this post on how to dress classy)
5. DO wear long tops or sweaters that cover your derriere.
6. DO wear the right underwear with leggings.
7. DO layer your tops to achieve balance.
8. DO wear leggings with the right shoes.
9. DO make sure your leggings are the right length.
10. DO make sure they are comfortable!

How Not to Wear Leggings

Along with the Do’s, there are Dont’s. These are the things you should avoid when wearing leggings. Again, these are some general guidelines.

11. DON’T wear crazy patterned leggings.
12. DON’T wear bright neon-colored leggings.
13. DON’T wear shiny spandex leggings
14. DON’T wear faded leggings, in any color.
15. DON’T wear leggings that are too loose or stretched out.
16. DON’T wear leggings that are too thin or see-through.
17. DON’T wear leggings to the office unless you dress them up.
18. DON’T wear leggings with holes, rips, or loose seams.
19. DON’T wear leggings with only a tight top
20. DON’T ever wear white leggings unless you’re wearing a long shirt, tunic, or dress with them.

Above all, make sure you feel comfortable in leggings, or don’t wear them at all. Confidence is key!

What to Wear With Leggings

Now that you know what leggings are, the best leggings to shop for, and some leggings style tips let’s review several stylish ways you can wear leggings.

Besides being comfortable, leggings are pretty versatile. You can wear leggings with a long tunic in the spring, with a cardigan for the fall and a coat for the winter. Switch up the shoes you wear with leggings from flats to heels and they go from casual to dressy. Let’s go over what shirts, sweaters, dresses, and shoes to wear with leggings.

Shirts to Wear With Leggings

The best shirts to wear with leggings are long ones. They cover your behind and make your outfit a little more presentable and elegant. Like mentioned in the style tips above, avoid shirts that are too tight, too short, or too sexy.

A button-down, slightly longer shirt is an excellent example of a shirt you can pair with leggings to create a cute outfit for spring. Like the polka dot shirt, I’m wearing in the outfit below.

In the springtime, the best shirts to wear with leggings are light flowy shirts. They create a great balance between form-fitting leggings and a lightweight shirt. (Do you want to learn more about what I mean by “balance” read How to Look Stylish Everyday – Your 5 Step Checklist). Look for long shirts made from silk, 100% polyester, or rayon fabrics. Also, since most likely you are wearing black leggings, add color, patterns, and dimension to your leggings outfit with the shirt! Have fun and pair your leggings with a paisley, floral, striped, or polka dot shirt.

For a dressy or business, casual outfit wear, a long shirt with black leggings. This is an example of a slightly long shirt you can wear with leggings. The black polka dots add some pattern and fun to this leggings outfit. I added a thick black belt to accentuate my waist because the shirt was too loose and flowy without the belt. A pair of burgundy pumps and a forest green bag complete this outfit. This is an example of how you can dress up a pair of leggings to look chic.

For casual days or a road trip, you could wear leggings with a chambray shirt, and a comfortable boyfriend tee. Complete this casual leggings outfit with a pair of flats, booties, or boots, and you are good to go. This combination is my preferred outfit for looking stylish on a road trip. Leggings are the most comfortable and stylish option for long hours of sitting. The layers allow me to peel off or add to, depending on the temperature in the car or outside.

Another popular combination is pairing a tunic with leggings. I don’t prefer this combination because it looks bulky and the tunic just takes over the outfit. I’ve seen plenty of tunic and leggings outfits and most of the time they look sloppy and too big. It might be because the tunic ends at mid-thigh, which is the thickest part of your leg, so the tunic only accentuates that.

Shop Tunics for Leggings

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Long Sweaters to Wear with Leggings

Long sweaters and leggings are some of my favorite combinations! This is not only an easy outfit combination but a stylish one too! Pair your black leggings with a gray, white, colored, or even off-white patterned cardigan like in the outfit example below.

A few style tips to keep in mind when putting together this outfit combination. For the shirt, you wear under your long sweater have fun and play with colors and patterns. Since you are adding a long sweater over your shirt, you can wear a form-fitting or shorter shirt. You don’t want the shirt you wear under your sweater to be the same length as your sweater, that will look too bulky and out of balance. Wear a shirt that is shorter, maybe ending at your hips or slightly higher.

When pairing your leggings with a long sweater wear a simple shirt, meaning no button-downs or anything with too much texture. The simplicity of the style of the shirt keeps your leggings outfit from being too much or too bulky. Think clean lines and correct proportions.

Pairing leggings with an oversized cardigan and high boots are classic for fall, not to mention warm and comfy. The bulk of the sweater offsets the narrowness of the leggings. I opted for a patterned cardigan that brought the eye up and paired it with a mustard tee to add a splash of color. This outfit is stylish, cozy, and my favorite way to wear leggings in the colder months.

Shop Sweaters to Wear with Leggings

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Dress with Leggings

A dress with leggings is very different from a dress with tights. I love pairing a dress with tights in the fall and winter. Just imagine, a forest green sweater dress with black tights and knee boots. I love it!! But I don’t wear a dress with leggings.

Remember the distinction I made above between tights and leggings; they are different. If you are considering wearing leggings with a dress, depending on the entire outfit and the occasion I would recommend switching them out for tights and see what you think.

Shoes to Wear With Leggings

Leggings are, first and foremost, casual wear, so that means that you can stick to more casual shoe options: flats, sneakers, converse, low ankle boots, and the like.

In the spring, a beautiful flat is a good casual option to wear with leggings. The falts can be a point or round toe, embellished or patterned (gotta love a good leopard print!). But do not wear flats that have an ankle strap or multiple straps that wind up the ankle. The strap will wrap around the end of your leggings creating a weird, clumsy look.

Boots and booties pair perfectly with leggings for cold weather, rain, and snow. The boots you wear with leggings can be flat, wedged, or heeled. If you are going to the snow, you can wear snow boots with your leggings outfit. And as you can see in the outfit example in this post, you can wear black leggings with brown boots!

If you need to dress up your leggings pair them with heels! A leggings outfit for a night out or work calls for pumps. Black pointy-toe black heels work for both day and night and create a classic outfit.

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Best Leggings for Work

As you can guess by now the best leggings for work, are high quality, thick black ones! I know, you’re probably thinking enough with the black tights I get it, but especially under this topic, I should reiterate it one last time. Black leggings are the best leggings for work!

A solid black pair of high-quality leggings can mimic skinny pants and be appropriate for work with the right fitted blazer. In this outfit, I kept a black-and-white theme. I paired black leggings with a white blazer and a large white scarf. This is an example of a no-nonsense outfit; I kept it classy and stylish to make it work-appropriate.

Pairing your leggings with a button-down is one of the simplest ways to pull them off. This look can go casual or slightly dressy, depending on the shirt, shoes, and accessories. Make sure that the shirt is long enough to cover your behind, and you can belt it to keep your shape as I did in this photo. Since a button-down is a classic shirt, keep the leggings classic as well and stick with black, chocolate brown or a dark navy, especially if you are wearing them to work.

When putting together a leggings outfit for work your shirt can be solid in a light color, or you can go with a print like this black-and-white polka dot. Note: If you are going to wear a patterned blouse, make sure that it’s a subtle and classic pattern that matches the outfit. You could also opt to wear a long-sleeve printed button-down shirt with your leggings and add a blazer and pumps for a stylish work outfit.

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Create Your Own Cute Outfits with Leggings

I hope this leggings style guide has answered many of your what to wear with leggings questions. You are now armed with the style tips to put together your own cute outfits with leggings.

If you have any questions or need specific outfit advice, please leave me a comment below!

Stay Stylish,
-V

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