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How to Wear Leggings: 16 Ways to Style Leggings

Are you a legging-lover with a growing collection of leggings? Or are you a one-pair, purist with a single black pair? No matter where you fall on the spectrum, you want to know how to wear leggings. 

How do you wear leggings? 

It can be a struggle. Celebrities and Pinterest posts make styling outfits with leggings look effortless. As you probably have found, there’s a fine line between athleisure and just-rolled-out-of-bed. It’s time to unleash your inner runway model and learn how to walk that line. Learn how to wear leggings (and elevate your style)  with these 16 ways to wear leggings. 

1. Create a Stylish Combo by Wearing Leggings with Boots

This one’s a classic. You can’t go wrong with leggings and a good pair of boots. Perfect for the fall and winter months, you can style this look to be casual or professional.

Depending on the type of boot you choose, it can completely change the look. 

Let’s look at how to wear leggings with boots.  

  1. Ankle Boots (Booties): These chic, versatile boots can go from professional to an evening out with friends. Go for a monochrome look to elongate your legs, and pair with a dressy shirt and blazer. Ditch the blazer after work.
  2. Knee High Boots: What goes best with a pumpkin spice latte? Tall boots, of course! For an undeniably autumn look, pair brown boots with black leggings. Wear a flannel or tunic to match.
  3. Combat Boots: Introduce a more masculine touch to your outfit with combat boots. Pair with a denim jacket to complete the look (and maybe add a band shirt in the mix.) 

2. Mix It Up With Capri Leggings

Capris can be tricky to style. If you’re not careful, they can visually cut your legs in half, making you appear shorter. Don’t give up on your capri leggings, though. They’re comfortable to wear—especially when the weather gets warmer. 

To avoid looking shorter, stick to the rule of thirds. Choose outfits that divide your silhouette into 1/3 and 2/3. For example, pair high wasted capris (2/3) with a crop top (1/3). Check out these ideas for how to wear capri leggings.

  1. High-waisted capris with a crop top
  2. High-waisted capris with a tucked-in shirt 
  3. Capris with a long tunic 
  4. Capris with a dress 

Our Women's Go Anywhere® 3/4 Pocket Legging is the perfect capri to pair with a crop top, tucked-in shirt tunic or dress!

Pink and maroon image comparing the correct way and incorrect way to wear capri leggings

3. Brighten Up Your Look With White Leggings

Black leggings are great and versatile, but what do you do when you want to wear an airy, pastel top? Unfortunately, black leggings will just weigh your outfit down. White leggings to the rescue.  

To wear white leggings, pair them with bright, patterned, floral tops and dresses. White leggings are especially great for spring and summer. When shopping for white leggings, pay attention to the thickness of the fabric (so nobody says “I see London, I see France”) Keep your undergarments on the down-low with these tips to banish panty lines

4. Add Some Fun With Patterned Leggings

Wondering how to wear patterned leggings? Whether they’re animal print, zigzag, polka-dots or anything in between, finding a matching top for those zany bottoms isn’t as hard as you think! There's one rule you should stick to when styling patterned leggings:

The Golden Rule: Don't mix patterned leggings with patterned tops. Other patterns are sure to clash with your already busy leggings. Let your leggings be the star of the show by rocking a solid color top.

If you’re going for a colorful look, find a solid color top using one of the colors from your leggings. If your leggings have black accents, consider a black top. Looking for an easy pair of patterned leggings to style? Check out our Women's Go Anywhere® Pocket Legging in Camo. This black and grey camo goes with anything! 

5. Find a Cool, Classic Look With a Denim Jacket and Leggings 

These closet essentials are a match made in heaven. Pair a denim jacket with leggings for an effortlessly cool look. You can dress this look up or down by changing your shoes or adding jewelry. Here are a few ideas for how to wear a denim jacket with leggings: 

  1. Classic: Denim jacket + white striped shirt + black leggings + booties
  2. Cute: Denim jacket + dress + black leggings + flats 
  3. Sporty: Denim jacket + hoodie + black leggings + sneakers 
  4. Boho: Denim jacket + solid tunic + patterned leggings + chunky jewelry 

Four circles filled with illustrations of different ways to wear a denim jacket and leggings such as in a classic, cute and sporty style

6. Stay Comfy and Casual With a Shirt Dress and Leggings 

Looking for a comfy, casual look? Pair leggings with a shirt dress for an outfit that’s both fashionable and functional. You could even wear this look as loungewear.

The great thing about shirt dresses is you can quickly style them to be more fitted or baggy depending on your mood. Wondering how to wear a shirt dress with leggings? Here’s some inspo:

  1. Casual: Shirt dress + denim jacket + leggings + sneakers
  2. Comfy: Shirt dress + cardigan + scarf + boots 
  3. Elevated: Shirt dress + belt + blazer + heels

7. Keep Cool While Wearing Leggings in the Summer 

Leggings aren’t just for jackets and boots—you can wear leggings in the summer too! When the weather gets hot, remember to keep your outfits light and breezy. Check out these tips for styling leggings for summer vacation:

Tip #1: Choose leggings that are light and breathable. Athletic leggings are great for the summer since they are often moisture-wicking. 

Tip #2: Avoid black leggings. Not only will black leggings hold in the heat, they will also make your outfit look heavy. Stick to brighter, lighter colors for the summer months.

Tip #3: Pair with flowy tops and dresses. Since leggings are form-fitting, create contrast by wearing a flowy top. Not only will it look great, but it will also keep you cool when it’s hot. 

Tip #4: Try out capri leggings. It’s all about staying cool in the summer. Want more coverage, but want to stay cool? Try pairing a shorter dress with capri leggings. 

8. Dress Up Your Leggings to Wear to Work 

Can you wear leggings to work? The answer is yes! You just have to be smart about how you style them. Consider choosing a sophisticated fabric for your work leggings, like leather or velvet. Then add jewelry to elevate the look. Finally, avoid neon and loud patterns. Neutral colors are great for the office.

Test out these tried-and-true ways to wear leggings to work: 

  1. Chic: Pencil skirt + black leggings + a tucked in blouse + heels 
  2. Comfy: Sweater dress + belt + leggings + booties 
  3. Classic: Long blouse + cardigan + leggings + slides 

Three circles filled with illustrations showing the different ways to wear leggings at work such as in a chic, comfy or classic style

9. Tips for Styling Leggings for Women Over 50 

Everyone can enjoy the comfort and flexibility of leggings—even women over 50. If you’re worried about showing too many curves, consider buying more structured leggings with thicker fabric. In the same vein, if you want to conceal your tummy, look for high-waisted leggings when you shop. 

Check out Tommy John’s legging collection, all with a double-layered waistband for extra support. 

10. Add Leggings to Your Winter Wardrobe 

Leggings go perfectly with jackets and boots—so of course, they are the ideal clothing item for the colder months. When shopping for leggings for winter, look for thicker fabric and full-length styles. 

Consider fleece-lined leggings if you like to be warm and cozy while on the go, like our Women's Go Anywhere® Fleece Lined Brushed Legging

Here are a few outfit ideas for how to wear leggings in the winter:

  1. Classic: Sweater dress + leggings + tall boots 
  2. Cool: Denim jacket + hoodie + leggings + sneakers 
  3. Cozy: Flannel shirt dress + cardigan + leggings + slides 
  4. Festive: Printed leggings + solid color sweater dress + booties 

11. Keep It Classy With Leather Leggings 

Sometimes you want to wear leather pants, without wearing leather pants. Leather looks chic, but can be uncomfortable. Leather leggings bring the best of both worlds to your closet: style and mobility. Wondering how to wear leather leggings?

A better question is how not to wear leather leggings because this wardrobe staple goes with anything. Combine with a stylish top and statement shoes for a fun night out, or dress them up to go into the office. 

12. Style in a Snap With a Denim Shirt and Leggings 

If you’re in a rush and need a simple, stylish outfit, make this your new go to. To wear a denim shirt with leggings, simply throw a denim shirt on top of a white tee, and you’re ready to go. If your denim shirt is long enough, you can wear it buttoned up by itself with leggings. Here are a few more ideas for how to wear a denim shirt and leggings.

  1. Denim shirt + white button-up + black leggings 
  2. Light denim shirt + black top + black leggings + black booties 
  3. Long denim shirt + belt + scarf + leggings + tall boots 

Pair your favorite top with our Women's Go Anywhere® Legging in black and a denim jacket, and you’re ready to go. 

Three outfit combinations including illustrations of denim shirts, leggings, booties and scarves

13. Lighten Up Your Look With Grey Leggings   

You probably own a pair of black leggings, but have you tried grey? If you want a wardrobe piece that’s just as versatile as black leggings, but visually less heavy, you will love grey leggings. Wearing grey leggings can be a little tricky, simply because there are so many shades out there. Here are some general guidelines for wearing grey leggings: 

  1. Light Grey: Provides a fresh alternative to black leggings. Pair with lighter, pastel colors for a more feminine look.
  2. Heather Grey: Looks sporty and pairs well with athletic tops and shoes. Style similarly to grey sweatpants.
  3. Dark Grey: Style these leggings the same as black leggings. Great for fall or winter.
  4. Metallic: Add some spontaneity to your wardrobe. These eye-catching leggings are great for a night out with friends. 

14. Get Up and Go With Sneakers and Leggings 

Did somebody say everyday outfit? Sneakers and leggings go together like cookies and cream. They are the pinnacle of athleisure and a staple for any legging aficionado. Check out these different styles of sneakers you can wear with leggings: 

  1. White sneakers: Great for a bright, minimalist look. Looks casual, but still put together. Consider pairing it with light grey leggings and a denim shirt.
  2. Athletic sneakers: Perfect for going to the gym, put on your favorite athletic shoes, and you’re ready to go. Pair with a hoodie or athletic jacket.
  3. Fashion sneakers: Eye-catching sneakers with a chunky heel or gold accents can take your leggings to the next level. Make it fashion, or make it office savvy.
  4. Slip-on sneakers: Slip-on sneakers are a great medium between athletic sneakers and fashion sneakers. Choose a solid color to pair with any outfit. 

15. Plan for Fall With a Flannel Shirt and Leggings 

Picture yourself at a pumpkin patch, under a tree with beautiful autumn leaves falling all around you. Maybe you even have a hot apple cider in your hand or a pumpkin spice latte. Ahh...life is good.

If this sounds like where you want to be, a flannel and leggings is the perfect look for you. To wear a flannel shirt with leggings, you have a few options. Wear a long flannel, buttoned-up by itself with leggings, or wear your flannel like a light jacket over a white shirt. If it’s cold, try adding a scarf, boots, and maybe even a beanie. 

Blonde woman wearing a dark flannel, leggings, and a hat looking over her right shoulder with her back turned

16. Stay Warm With Velvet Leggings 

Velvet leggings can be a great way to introduce a pop of color into your outfit—while still looking sophisticated. These soft leggings are great when the weather gets a little colder. They can even add some texture to your outfit, that leggings often leave out. Check out these ideas for how to wear velvet leggings: 

  1. Monochrome: Pair black velvet leggings with an all black outfit. The texture of velvet will help break up your outfit.
  2. Nude top: Wear a nude or neutral top to let the elegance of velvet leggings shine through.
  3. Sweater: Rock a sweater and velvet leggings for a warm and cozy winter look. 

What to Wear With Leggings?

Looking for more legging outfit ideas? Thankfully, leggings go with just about anything. They are a great wardrobe staple that you can style for almost any occasion. 

Here is a list of popular items to pair with leggings:

  1. Denim jacket
  2. White shirt 
  3. Flannel shirt 
  4. White and black striped shirt 
  5. Tunic 
  6. T-shirt dress
  7. Sweater dress 
  8. Booties or ankle boots
  9. Tall boots or knee-high boots 
  10. White sneakers
  11. Fashion sneakers 

Additional Considerations When Choosing Leggings 

Ready to find the perfect legging to match your style? There are a few things you should consider when shopping: color, length, and fabric. Also, think about your overall style. Are you looking for a statement piece or a versatile staple to add to your wardrobe? 

Color

Black is the most popular color for leggings—and for a good reason. It truly goes with anything and goes anywhere like our Women's Go Anywhere® Legging

A close neighbor of black is dark grey or light grey. These neutral colors are still versatile, but look a bit more modern. In the same vein, white leggings are also a team player. They go with anything, but might be better for you if you plan on styling brighter colored outfits. 

Finally, consider stepping outside the box and choosing a colored velvet legging or patterned legging. These pieces will add some spice and variety to your closet. 

Length

Full-length leggings are the standard. These leggings are great for working out, since you won’t have to worry about your leggings moving around while you work out. Long leggings work well as pants or tights. 

If you like wearing leggings in the summer, consider buying capri leggings. Not sure how to wear them? If you have a short dress, you can make it look more modest by adding capri leggings. These cropped leggings are great for transitioning in-between seasons. 

Fabric

Which fabric works best for you? If you work out or travel frequently, look for breathable, moisture-wicking fabric. With any legging, make sure the fabric is thick enough that it’s not see-through.

If you plan on styling more formal outfits, consider introducing some texture with either velvet or leather leggings. Finally, if warmth is important, consider looking for thicker leggings or fleece-lined leggings. 

As you can see, leggings can do a lot. They’re not just for working out, they’re also great for going to the office, traveling on a plane, or just everyday wear. If you felt lost before about how to wear leggings, you now have lots of options. 

Looking for a versatile, everyday legging? Check out Tommy John’s collection of leggings. They have a variety of colors and designs to fit any style.