What To Wear With Leggings

As the world transitions to colder weather, it’s time to put the biker shorts away for the winter and replace them with a tried-and-true favorite of mine. That’s right; it’s officially leggings season.

While many associate a pair of leggings with comfy athleisure, there are so many ways to style leggings ranging from a casual look to a classy and chic vibe. Luckily, I have some outfit ideas in mind that will make you love leggings this season. 

Read on for eight different ways to style leggings for any occasion.

What Exactly Are Leggings?

Before I can give you tips on what to wear with leggings, I have to clarify and distinguish what leggings actually are. That way, you know what to look for when you add some to your wardrobe.

It’s important to know the difference between leggings and tights because they suit different purposes. Tights are almost always made out of sheer fabric, while leggings are typically made with opaque fabric.

Leggings and jeggings (leggings that emulate skinny jeans) also end at the ankle, while tights cover the whole foot. While they serve similar purposes, oftentimes, leggings are a versatile garment that can be worn as both athleisure and a classy outfit.

Pair With a Blazer To Achieve a Classy Look

This look is perfect for all the girl bosses out there who want a professional and simultaneously comfy outfit. To achieve this look, start with thick, high-quality black leggings. Then, grab your fav trendy button-down or a long tunic top. Finally, layer a blazer on top. Ta-da!

Keep in mind that not all leggings are made of cotton or super tight, so it’s easier than you think to make leggings look professional. For any work-from-home warriors out there, this is the perfect outfit for around the house.

If you’re wondering how to style a blazer, review the basic blazer guidelines and then shop with confidence.

Perhaps you’re going for a more laid-back look. In that case, an oversized blazer with a tighter pair of leggings is fabulous for fall. Also, I’ve said it before, but I love wearing white after Labor Day. It’s a snap to style a white blazer — statement jewelry and leggings have never looked so good.

Sport a Trendy Set

Surely you’ve seen the trend all over the place, and it’s for a good reason—I absolutely love athletic sets. Not only are they fashionable, but they are pretty perfect for making waves while walking. 

Matching sets are a classic, but you can also get creative. Some of my favorite sets are high-waisted leggings paired with a more cropped, sports bra-type tank top or shirt.

Take a look: Designer Lhasa Fitwear has an oh-so-chic solid color set (I love green, in particular for fall), and it’s extremely versatile. It can be worn to work out or to wear as athleisure around the house or to run errands.

Are you a trendsetter at the gym and a cozy comfort icon at your local coffee shop? Well, these abstract leggings are a great option if you’re going for a funkier, fashionable look. 

Stay Comfy and Cute With an Oversized or Long Sweater

This is the perfect outfit for one of those in-between-days when it’s not quite cold enough to bring out a jacket, but you’re definitely In need of a sweater. Oversized sweaters, whether turtlenecks, crews, or v-necks, are lovely with a pair of leggings. Make it a head-to-to ensemble with a soft beanie and suede booties.

Right now, chunky, curb-stomper-type boots are in style, and they complement the leggings nicely, like these Elán boots that are perfect for fall. This outfit with leggings is excellent for a casual dinner or a daytime fall activity.

Faux Leather Leggings

If you haven’t hopped on the faux leather pants trend yet, it’s becoming a wardrobe staple, and I don’t think you’ll regret buying a pair.

If you’re unsure how to style leather pants, consider trying out a pair of leather leggings. They immediately make your outfit look 100% more chic; they’re an easy way to get dressed up in the fall and winter time. What’s fab is that you can really wear whatever you want on top.

For colder weather, an oversized sweater looks great with leather leggings and boots. For going out, a pair of high-waisted leather leggings and a tank top, bodysuit, or crop is so cute for this season. If you need it, I have even more tips on how to style leather pants.

Button-Down or Long Cardigan With Leggings

There are several ways to pull off the look of this outfit; you could style a pair of high-waisted leggings with a bralette or crop top and pair it with an oversized or fitted button-down. This looks flawless with jeans, but to make it a little more comfy and casual, leggings are perfect.

If it’s colder out and you have a cardigan you’ve been dying to pull out of the sweater vault, this Is your chance. I like wearing an outfit like this around the house or cooking a meal at home. It’s also extremely versatile — you can style the same pair of leggings in so many ways.

Leggings Underneath a Sweater Dress

If it’s leggings season, that also means it’s sweater dress season, which is another necessary wardrobe staple. But have you tried incorporating them into one outfit before? Well, it’s certainly worth trying, especially on cold days when you want to wear a dress, but even tights are too cold.

The key to this outfit is to find the right length of the sweater dress and pair it with the right shoes. I adore a classic ballet flat, for instance. Or, if you want a bit dressier, knee-high boots or ankle-height boots are also a great option. (Ps: check out my tips on how to style a sweater dress for fall.)

Flare Leggings Forever

If you haven’t heard or seen it, it’s apparent that in 2022, yoga pants have become an evergreen wardrobe staple since their reinvention in 1998.

When you think about it, they’re essentially just flared leggings, and if you’re wondering what to wear with yoga pants, look no further.

Similar to traditional leggings, a comfortable tank top paired with a cardigan or jacket is perfect for a laid-back, more chill outfit for fall. While it’s harder to make yoga pants look dressy, they’re certainly comfortable and darling.

Oversized Hoodie, Denim Jacket, or Plaid Shirt

Matching sweatshirt-sweat pant sets are super trendy right now, but I think this trend should apply to a matching sweatshirt-legging combo as well! A simple hoodie and leggings paired with a denim jacket and a long top with a flannel pattern not only screams fall but will keep you so warm.

I believe that some good long-sleeve outerwear for fall is essential, and if you want an alternative to an all-denim look, leggings are it. For shoes, a pair of white sneakers or ankle boots will always look good with leggings.

This style is also an excellent opportunity to try out a pair of colored leggings. Don’t be afraid to have fun with it, especially if paired with a more low-key hoodie. 

Get a Leg Up On the Day

The best leggings are the ones you are comfortable in — so keep that in mind when you’re finding the perfect ensemble for whatever look you’re going for! Another reason I love wearing leggings is that they can really fly under the radar in an outfit, or they can be the main piece that draws the most attention.

And most importantly, they can be worn in nearly every situation, which makes it easier to put together outfits on a daily basis, in my humble opinion. Whether it’s a casual outfit or a classy event, you can always find an excuse to wear leggings.

I hope this inspired some ideas for what to wear with leggings as we approach cold weather, and remember to wear what makes you feel good!

Sources:

Is No White After Labor Day Fact or Fiction? Here's What the Experts Say | Newsweek

How Did Athleisure Take Over American Fashion? | The Atlantic

How America Became a Nation of Yoga Pants | Bloomberg