As far as comfort goes, not many clothing items can compare with leggings. They hug your legs and hips snuggly without being too tight, and they come in many different styles, colors, and sizes. 

However, their versatility can make them a bit challenging to style. Namely, most people aren’t sure what to wear with leggings and how to make them fit into their everyday outfits. 

Fortunately, this article is here to help you. Follow along to see the season’s 6 best looks for leggings!

What to Wear With Leggings: Stylish Ideas 

Classic Button-Down Shirt

Leggings and a button-down are one of the most common casual combinations you can go for. When styled right, this mix can be suitable for any occasion, from a day in the office to an evening out with friends. 

The most important thing to remember when styling leggings this way is that your shirt should be on the longer side. In other words, it should cover your behind at least partly and reach the beginnings of your thighs. 

As for the size, always go for shirts that are slightly bigger than what you usually wear. That way, the looseness shirt will offset the form-fitting nature of the leggings nicely.

Moreover, you should never tuck the shirt inside the leggings, since they are too tight for it. Instead, leave the shirt out and button it up completely. To finish the look, you can go for some nice flats or sneakers. Remember that this outfit is all about feeling good in your skin while still looking great, so only pick footwear that is comfortable. 

Oversized Jumper

Just like a flowy shirt, long oversized jumpers also look great with leggings. This combo is equally cozy and stylish, and it will keep you warm despite the temperature outside. 

You can pick pretty much any style of jumper for this outfit, be it a one-piece or a button-down model. As long as it’s warm and long, it can work. In addition, any color goes as long as it matches the leggings themselves. 

As for your footwear, this particular combination requires something sturdy but fashionable. Thus, you cannot go wrong with a pair of quality ankle boots, be it a flat or heeled model. 

T-Shirt-Cardigan Combo

This particular look is ideal for long days at work where you need to look sharp but you still want to feel comfortable. However, it is just as suitable for going out to lunch or dinner with friends or a casual date. 

After you pick your leggings, you should go for a tee in a neutral color. That includes white, black, beige, or gray. Then, complete the outfit with an oversized cardigan. It can be a model with buttons or one that doesn’t close at all. 

The cardigan should be longer, reaching to about mid-thigh. As for the tee, it’s best to opt for a model of medium length that reaches right to your hips. If you have a longer model in mind, you can tie it and integrate it into the outfit that way. 

And last but not least, you can pick pretty much any shoes for this outfit. From flats and sneakers to ankle boots and converse, anything goes as long as you can color-coordinate it with the rest. 


Of course, no list of stylish looks with leggings can go without the classic hoodie pairing. Perfect for lounging at home, running errands, or going to class or the gym, this outfit puts comfort above everything else. Plus, it’s incredibly warm and great if you have to spend a lot of time outside. 

For this outfit, you should put on your favorite pair of sneakers. In addition, you can don a leather jacket and complete everything with a pair of sunglasses. Even if there isn’t much sunlight outside, they’ll complement your outfit wonderfully. 

Fitted Blazer

Are you looking for a way to make leggings a staple piece in your work outfits? Well, all you need is to find a pair of solid black leggings made of quality cotton and polyester. For one, they can easily mimic black skinny pants. Even more importantly, they can make you look serious and elegant when combined with an appropriate fitted blazer. 

This blazer can be in a solid color or with a plaid pattern of some kind. You can also pick a black one, so it fits the leggings perfectly. However, if that’s what you go for, make sure you pick a tee or shirt that is bright to offset the colors and make your outfit pop. 

Finally, this look cannot be complete without a pair of high heels, a big handbag, and some cute jewelry. Just make sure it fits with the rest of your clothes color-wise, and you’ll be good. 

Denim Shirt and Tee

Last but not least, we have another casual outfit that can become dressy with the right accessories. Namely, you can combine your favorite leggings with a light denim shirt and a T-shirt underneath. 

While any leggings can work with this idea, we suggest you go with a black model made of leather. They will add an edgy note to your outfit and make you look stylish and mysterious. 

The denim shirt can be in any shade you like, although lighter models will work best against the darkness of your leggings. Length-wise, you should opt for a shirt that either comes to your hip or your mid-thigh. 

Lastly, the key to this outfit is to leave the shirt open so that the tee underneath is fully visible. You have two choices when it comes to the T-shirt: you can pick either a neutral one or a vintage model with a funky print on it. Add some jewelry and your favorite heels, and you’ll be ready for your day!

What to Wear With Leggings: Final Thoughts

Now that you know what to wear with leggings, it is time to think of all your upcoming outfits. From hoodies that will keep you warm to fitted blazers appropriate for work, there are no limits to what you can combine with this versatile garment. So, get creative, and don’t be scared to experiment!