How to Wear Dresses With Leggings

Have you ever been out shopping and seen 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 really loved, here’s another way to think about wearing it. Many short dresses look fabulous when you wear them over dark, opaque 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 full figured.
  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, just watch that if they are slim fitting, you don’t see the waistband of the leggings underneath.
  4. Sweater Dresses – These look fab with leggings and flat riding boots in fall and winter.

floral dress with leggings

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 length, but remember that anything past the knee will drag the outfit down and make you look dowdy.

A few other things to keep in mind. This is the type of outfit that can look edgy chic or like you were totally confused about what to wear that day.

floral dress with leggings

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 very slimming color.
  • Avoid dresses in junior or baby 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 a lot of stuff 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 dresses do not.
  • Have you ever seen a cute dress that you wanted to buy, but felt it was just too short? Why not add leggings? Here’s how to wear a dress with leggings. 

    You can wear a

    • shift dress
    • sweaterdress
    •  shirt dress

    straight up and down work better than flare.

    Blue Print 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 looks best. I think she looks great either way.

    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 either.

    2. The Length: This dress covers her bottom and a little more, which is essential when you wear leggings. This is how to wear leggings, so you 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 co-ordinated outfit, not some random pairing.

    4. The Right Footwear:LaAnja was smart 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.

    Deborah Boland 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 to 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, and it is so comfy too. It’s a nice change from jeans.

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

Join the Conversation

4 thoughts on “How to Wear Dresses With Leggings

  1. Hello I’m Cheryl,

    Im a women who is 55 and I’m pretty much am doing what you suggest already, but love some of your “”not to do” suggestions! Just in case I get tempted, because something fits doesn’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: http://rstyle.me/~9ynqI
      I’ve been wearing that for years. When I want something slightly heavier I wear Bobbi Brown Skin foundation in Warm Ivory:http://rstyle.me/~9ynlO
      I have fairly dry skin and I find this is not drying and goes on really smoothly- great coverage, but not thick. I hope that helps.