Leggings are one of the most comfortable items you can wear, but this go-to wardrobe staple has its detractors. The principal complaint from the naysayers is how leggings are worn and what leggings are worn with. Well, I love leggings and I’m here to help you pair those leggings with stylish options, especially now that fall is upon us.

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 strong. They may change material and colors from season to season, but you can wear classic leggings every year.

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

Let’s start with a few style tips….



  1. DO wear proper-fitting leggings.
  2. DO stick to dark colored leggings.
  3. DO stick to solid or Fair Isle leggings.
  4. DO keep it classy, not sexy—unless you are going for sexy, of course.
  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. DON’T wear leggings as pants.
  11. DON’T wear crazy patterned leggings.
  12. DON’T wear bright neon-colored leggings.
  13. DON’T wear shiny spandex or leather 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!


Now that you know what you should and shouldn’t do when wearing leggings, let’s review several stylish ways you can wear leggings.


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, like 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.

Your shirt can be a 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.) Since it is fall, you could opt to wear a long-sleeve printed button-down shirt with your leggings and add a scarf and some boots for warmth.

What do you think of my stylish leggings outfits? Tweet me “love it!” if you think I pulled off leggings in a classy and stylish way!


Pairing leggings with an oversized cardigan and high boots is classic for the 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 brings 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.

If a bulky cardigan isn’t your thing, try pairing your leggings with a tee and a boyfriend cardigan. These longer sweaters are slimming and hit mid-thigh, covering your assets.


For casual days, think leggings and chambray. It’s a nice play on wearing denim. I like to pair these two with a soft and comfy boyfriend tee. Finish it off with a pair of flats, booties or boots and you are good to go. In fact, this is by preferred outfit for long road trips. 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 when we stop.


Lastly, for a dressier option, pair leggings with a stylish blazer. A solid black pair of high-quality leggings can mimic a skinny pant and go upscale with the right fitted blazer or jacket. In this outfit, I kept a black-and-white theme. I paired black leggings with a white blazer and large white scarf. There was no nonsense with this outfit; I kept it classy.


One of my early style tips refers to wearing the right shoes with your leggings. Leggings are, first and foremost, casual wear, so that means that you should stick to more casual show options: flats, booties, knee-high boots or tennis shoes. The exception to this rule is if you have a good high-quality pair of black leggings paired with something more formal, like a blazer, you can wear a pair of pumps. (But steer clear of ankle strap, or stiletto heels with your legging outfits.)

When the weather isn’t too cold, a nice flat is a good casual option. It can be pointed or round toe, embellished or patterned (gotta love a good leopard print!). Do not wear flats that have an ankle strap or multiple straps that wind up the ankle.

Boots and booties pair perfectly for cold weather, rain, and snow. They can be flat, wedged, or heeled and, if you are going to or are in the snow, you can wear snow boots with your leggings outfit. Keep the stiletto and over-the-knee boots in the closet for another occasion.

For a fun and casual look, you can even pop on some classic Converse (low or high-top).

I hope that this post answered a few of your question what to wear with leggings! For more fall style ideas, check out 80+ Cute Fall Outfits for Your Inspiration.

Stay Stylish,

Keep visiting Sassy Lady.


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