Eke Esther

Leggings are some of the most comfortable pieces of clothing you can own, but they also have their critics. It can be difficult to know how to wear them and what to wear them with. I am a huge fan of leggings, so I am here to help you turn this beloved item into fashionable leggings for fall, winter and spring outfits.

For centuries, leggings have been made of different materials and used for various purposes. They have adapted, updated and transformed into a wardrobe staple, and they are still going strong today. They may change in material and colors from year to year, but you can still wear a classic black pair of leggings year after year.

If you’ve been hesitant to try out leggings, have been criticized for wearing them, or just want to update your look for cooler weather, then make sure you read the entire post. I will show you what you need to know to create cute legging outfits that will get you almost anywhere.


How to wear leggings

Before we dive into what to pair leggings with, I want to be clear about what I mean by “leggings”. I don’t mean workout leggings you want to pass off as casual everyday wear. The type of leggings I’m referring to in this style guide is black leggings, sometimes black leather leggings, or dark grey end at the ankle leggings. These are made from a thicker fabric and don’t extend to cover your foot.

In previous blog posts, I’ve also talked about how leggings are sometimes confused with “tights.” Tights, on the other hand, go from the waist up to the toes and come in completely opaque, opaque, or sheer. Tights come in all sorts of crazy colours, prints and textures.


When looking for a good pair of leggings, make sure they are made of thick, dressy material. You don’t want anything that’s see-through, so make sure they’re soft and comfortable. They should also be in a form-fitting way, so they don’t hug your legs and clump together. Too thin leggings can make you feel unsupported and uncomfortable, so make sure you’re getting the right fit.

A good quality legging will cost more and may seem like an investment, but it’s worth it if you can wear it for different occasions all year round. A good quality legging is also versatile, so you can wear it to work, to a cocktail party, or on a casual weekend, with a cardigan or a tunic.


I’m going to go over some dos and don’ts for leggings that I’d like to share with you. These are just general style tips to follow, but sometimes they can be broken if the outfit looks really nice. (For example, see our winter legging outfits below).

These are just some general style tips for leggings:

  • Wear proper-fitting, dark-coloured, solid-coloured, classy leggings, not sexy leggings (unless you’re going for sexy)
  • Wear long-sleeved tops or sweater that cover the derriere
  • Wear the right underwear
  • Layer your tops for balance
  • Wear leggings and the right shoes
  • Make sure your legging is the right length


In addition to the Do’s, there are also the Don’ts. Here are some general tips to keep in mind when it comes to leggings: 

  • Don’t wear crazy patterns, 
  • Avoid bright neon colours, 
  • Don’t wear bright spandex, 
  • Don’t wear faded, in any colour
  • Don’t be too loose or stretchy
  • Don’t have a see-through, too thin, or too see-through legging
  • Don’t pair them with a tight top unless you’re dressing them up
  • Don’t ever pair them with a long shirt or tunic unless you’re wearing them with a long-sleeved shirt or dress.
  • Most importantly, don’t wear them if you don’t feel comfortable in them or if you’re not confident in them.


Now that you’re familiar with the basics of leggings, the best ones to buy, and some legging style tips, let’s take a look at some of the most fashionable ways you can wear them.

Leggings are not only comfortable, but they’re also very versatile. In the spring, you can pair them with a tunic, in the fall with a cardigan, and in the winter with a coat. You can switch up your shoes from flats to heels, and they can go from casual to formal.

Let’s look at the different types of leggings you can wear, from shirts and sweaters to dresses and shoes.


Long shirts are the best for pairing with leggings as they cover your behind and add a touch of elegance to your outfit. As mentioned earlier in the style tips, don’t go for shirts that are too loose, too short or too sexy. A button-down, a slightly longer shirt is a great example of a shirt that can be paired with leggings for a cute spring outfit. For example, I am wearing this polka dot shirt in the below outfit.

Tunics and leggings are another popular combo. I personally don’t like this one as it looks bulky, and the tunic will just take over your outfit. I have seen many tunic and legging outfits and most of them look sloppy and oversized. This is because the tunic stops at the middle of your leg, which is the most thick part of your leg.


Combining long sweaters with leggings is one of my favourite outfits! Not only is it an easy combo, but it is also one of the most stylish! You can pair your leggings with gray cardigans, white ones, coloured ones, or even an off-white cardigan as shown below.

Here are a few style tips to remember when creating this outfit combination:

For the shirt, wear it under your long sweater. Experiment with different colours and patterns. Because you are wearing a long sweater over the top of your leggings, you can choose a form-fitting, shorter shirt. Don’t wear a shirt that is the same length as the sweater, as it will look bulky and out of place. Instead, wear a shorter shirt, which may end at your hips, or slightly higher.


A dress with a pair of leggings isn’t the same as a dress with no leggings at all. I love wearing a dress and tights together in the fall/winter. Just think forest green sweater dresses with black leggings and matching knee boots! I love it! 

However, I do not wear a dress and pair leggings together. Remember what I said above about tights vs leggings? They’re not the same. If you’re thinking about pairing leggings and a dress, it depends on the outfit you’re wearing and the event you’re attending. I would suggest pairing them with tights and seeing how you feel about it.


Leggings are meant for casual wear, so stick to more casual shoes like flats, sneakers, and converse. In the spring, a nice flat is a great casual option to pair with leggings, the falts can be point or round, embellished, or patterned (love the leopard print!). Don’t wear flats with an ankle strap, or multiple straps that wrap around the ankle, as this will make your leggings look weird and clumsy.

Leggings pair perfectly with boots and booties, whether it’s cold, rain, or snow. If you’re headed to the snow, pair your leggings with snow boots. As shown in the outfit example below, you can wear a black leggings outfit with brown boots.

If you’re looking to dress your leggings up, pair them with heels. A legging outfit for a night on the town calls for a pair of black pointy-toe heels, and a pair of black heels for a classic outfit.


As you may have guessed by now, the best type of leggings to wear to work is high quality thick black leggings. I know you are probably thinking enough about the black tights, but I will reiterate it again under this topic, black leggings are best for work! 

A good quality black pair of high quality leggings can look like skinny pants and be suitable for work when paired with a fitted blazer. 


I hope this guide has provided you with all the information you need to know about how to style your own leggings outfits. Now that you have all the style tips you need to create your own cute leggings outfits, let me know what you think in the comments section below!

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Eke Esther is a professional content writer that focuses on fashion and lifestyle. She has worked as a freelancer for years, helping several organizations achieve remarkable results. Giving you the newest fashion designs and trends is her main goal. You'll get blogs of the highest caliber that fit your tastes.
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