How to Wear Dresses With Leggings

Have you ever been out shopping and see the most darling dress, but you stopped yourself from buying it because it was too short? If you’ve ever passed on a dress that you loved, here’s another way to think about wearing it. Many short dresses look fabulous when you wear them over dark, opaque leggings.

darling dress with leggings



The challenge is that not all dresses are created equal. The dresses that work best worn with leggings are:

  1. Flowy Dresses – The wide over narrow silhouette is very flattering, especially if you are fully figured. Just make sure they are not too wide like a stiff bell.
  2. Shirtdresses – Usually, they are just a tad too short to feel comfortable to wear with bare legs. Try one with leggings and a belt, sandals or flats.
  3. Tunic Style Dresses – Very popular; watch that if they are slim fitting, you don’t see the waistband of the leggings underneath.
  4. Sweater Dresses – These are one of my favorites and look fab with leggings and flat riding boots in fall and winter. Learn more about how to wear sweater dresses with leggings!


sweater dress with leggings and brown boots

Correct Length

The length of your dress can vary from mid-thigh to above the knee. If you are heavy on the bottom or thighs, lean towards the longer distance, but remember that anything past the knee will drag the outfit down and make you look dowdy.

shirt dress with leggings



Here are a few other things to keep in mind. This outfit can look edgy-chic or the opposite -like you were confused about what to wear that day.

To keep your dress and leggings outfit looking purposeful, mature, and sophisticated, follow these guidelines:

  • Stick to black leggings- the perfect canvas for your dress and a slimming color.
  • Avoid dresses in junior or loud colors like bubblegum pink.
  • Choose modern prints like graphic designs or bold florals rather than cutesy prints or tiny granny florals.
  • Dresses with clean lines and minimum detail work better than dresses with frills, flounce, or many things hanging off them.
  • Avoid babydoll style dresses – too junior.
  • Dresses with some black in them to tie into the black leggings look most chic.
  • Simple, informal short dresses work. Fancy formal short skirts do not unless they are very Minimalistic.

short dress with leggings




red dress with leggings


  • My reader, LaAnja, found this dress at Ross for $12.99 and was inspired to wear it with leggings.dress with leggings She wondered which way looked best. I think she looks great either way.


ross blue dress with leggings

What makes a dress with leggings work?

1. The Style of the Dress:  This tunic style works perfectly with leggings because it is slim-fitting but not tight. You don’t want anything clingy, but you don’t want it too baggy.

2. The Length: This dress covers her bottom and a little more, which is essential when wearing leggings. This is how to wear leggings to look classy and not trashy.

3. The Color: It’s gold with black, which means the black picks up on the leggings and makes this look like a coordinated outfit, not a random pairing.

4. The Right Footwear: LaAnja was wise to keep her flats black like her leggings. All one color creates a long, lean line that makes her look taller and slimmer and keeps the emphasis where it should be on that beautifully patterned tunic dress.


sky blue dress with leggings

The Shirtdress + Leggings

Here’s me in another type of dress that works well with leggings. I loved the color and pattern on this airy shirtdress but felt it showed too much leg, so I threw on a camisole, rolled up the sleeves, and belted it at the hip to give it a sporty look.

Then I added some brown leggings and a fabulous pair of merlot suede boots. I love to wear this outfit in the fall when I go shopping or run errands; it is so comfy. It’s a nice change from jeans.

So remember, think tunic or shirt dress if you want to wear clothing with leggings. These dresses look most like long shirts and will work the best. Maybe you’ve even got one you want to experiment with in your closet? Please send me a photo. I’d love to see how you style it.

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6 thoughts on “How to Wear Dresses With Leggings

    1. Hi Ellen, I agree that a shirtdress over leggings gives a very chic look. The proportions make it very figure-flattering to when you have wide over skinny. Thanks for stopping by!

  1. Hello, I’m Cheryl,

    I’m a woman who is 55, and I’m doing what you suggest already, but I love some of your “not to do” suggestions! Just in case I get tempted because something fits don’t necessarily mean I should wear it! LOL

    Thank you sincerely,

    1. Hi Shannon,
      I find that I like a light foundation as I age. For every day, I like Laura Mercier tinted moisturizer in the shade, Nude:
      I’ve been wearing that for years. When I want something slightly heavier, I wear Bobbi Brown Skin Foundation in Warm Ivory:
      I have pretty dry skin, and I find this is not drying and goes on smoothly- great coverage, but not thick. I hope that helps.

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