Just because they’re comfy doesn’t mean leggings aren’t stylish. One way to elevate your leggings looks is to wear them with dresses. But, you have to be careful to choose the right dress style to look chic rather than overly casual. In this article, you’ll find all the best dresses to wear with leggings.

What type of dresses go with leggings?

You can pair any length of dress with your leggings. But unless you are wearing your leggings simply for warmth underneath and not to be seen, you will want to ensure your dress is short enough to see your leggings. Alternatively make sure your dress has a leg slit or buttons you can unfasten to create the perfect leggings and dress look.

Your dress over leggings look will also look best if your dress is two-thirds of the overall look and your leggings one-third.

Can you wear leggings with dresses?

Dresses to wear leggings with - Karen wears an all-black outfit  | 40plusstyle.com

Of course. This is a look that has remained on trend for many seasons. Wearing your leggings with a dress is a great way to add warmth so you can wear your dresses in cooler months. Karen @styledbykaren above shows how you could wear leggings with a longer button-down dress and booties.

Recreate her outfit with this similar dress (other options here and here), leggings and booties.

It’s also a great way to wear your shorter dresses in fall or winter.

What to consider when choosing dresses to wear leggings with

What should you think about if you’re shopping your closet or choosing dresses specifically to go with your leggings.

1. The color of your leggings

Darker leggings and jeggings are more versatile than paler or more colorful options. If you want to be sure that your dress and leggings outfit is timeless and flattering, choosing leggings in shades like black, gray and navy is a safe, stylish option.

2. Do you need seamless leggings?

Depending on how tight the dress you wear is, you may want to consider seamless leggings, in the same way you look for seamless underwear. That way, you can ensure you have a smooth silhouette.

3. Re-jig your wardrobe

Thinking about wearing your dresses with leggings means you can wear dresses you might have pushed to the back of your closet again. For example, your shorter dresses might not have been on your radar for a while, but get them back out again and try them on with a pair of black leggings.

Dresses to wear leggings with - Josephine wears a pink dress and leggings | 40plusstyle.com

Josephine @chicatanyage above (read her style interview here) wears her black leggings under a bright dress.

Get her look with this similar dress (another option here), leggings, shoes and scarf.

4. Show a bit of leg

While you aren’t obviously showing off your legs as such because you are covering with leggings, dresses over leggings work best when you can see your leggings. So look for mini and shorter styles, or longer dresses with a leg split or with buttons so you can show off as much of your leggings as you want.

Leggings to go with dresses

Some of the most versatile leggings you can choose with your dresses are classic black and dark blue jeggings. You could also opt for coated or leather leggings for evening for a more edgy look.

Leggings to wear with dresses | 40plusstyle.com

Zella Live In High Waist Leggings1822 Denim Butter JeggingsSpanx Faux Leather Leggings

Dresses and leggings outfits

Let’s look at some dresses and leggings combinations to choose from, as well as why our chosen dress styles work with leggings.

Mini dress and leggings

A tunic goes beautifully with leggings. You’ll see plenty of leggings and tunic suggestions in our popular article on how to wear leggings over 40. A mini dress will give you a similar look to a long top. It’s a great way to wear shorter dresses if you don’t want to show off too much leg.

Mini dress and jeggings | 40plusstyle.com

SIMKHAI Roma Draped Satin Minidress1822 Denim Butter JeggingsNYDJ Gabbe Block Heel Booties (Amazon) – Tory Burch Reva Leather Clutch-On-ChainShashi Shashi Lynx 14K Gold-Plated Hoop Earrings

Dresses to wear leggings with: 9 ways to wear your dresses with leggings | 40plusstyle.com

Jess @elegantlydressedandstylish above (read her style interview here) mixes textures with her lace and leggings outfit.

Steal her look with this similar dress (other options here and here), leggings, booties, handbag, necklace and earrings.

Asymmetric dress and leggings

We’re a huge fan of asymmetry at 40+ Style. Asymmetric dresses are perfect to wear with dresses as the high-low hemline shows off some of your leggings at one side, and the diagonal lines of the hemline add a flattering, elongating effect.

Asymmetric dress and jeggings | 40plusstyle.com

Derek Lam 10 Crosby Maddison Asymmetric Shirtdress1822 Denim Butter JeggingsNYDJ Gabbe Block Heel Booties (Amazon) – Tory Burch Reva Leather Clutch-On-ChainChan Luu 18K-Gold-Plated, Citrine & Freshwater Pearl Y Necklace

T-shirt dress

For a casual option, a t-shirt dress is the perfect choice. Team with your sneakers or booties, and add a shorter blazer or cardigan if you need extra warmth. You can always elevate your look with a statement necklace.

T-shirt dress and jeggings | 40plusstyle.com

Eileen Fisher Crewneck Wool T-Shirt Dress1822 Denim Butter JeggingsDr. Scholl’s Shoes Time Off SneakerTAKEASY Genuine Leather Italian ToteKenneth Jay Lane 14K Gold-Plated & Faux Emerald Glass Stone Toggle Necklace

Shirtdress

A shirtdress is a lovely option with leggings, as the flowy lines of the dress contrast well with the tight fit of your leggings. Choose a long tunic style, or opt for a shirtdress with buttons so you can leave a few buttons unfastened at the bottom.

Shirt dress and leather leggings | 40plusstyle.com

COS Fluid Twill Shirt DressSpanx Faux Leather LeggingsDolce Vita Nadav Ballet FlatTory Burch Reva Leather Clutch-On-ChainChan Luu 18K-Gold-Plated, Citrine & Freshwater Pearl Y Necklace

Sweater dress

Choose a sweater dress with your leggings to stay cozy in cooler months. Opt for a fitted or looser style, depending on your preference. Both will go well. Add boots or booties and a long coat and you’re ready for any weather.

Sweater dress and leggings | 40plusstyle.com

Vince Camuto Metallic Long Sleeve Rib Sweater DressZella Live In High Waist LeggingsNaturalizer Wrenley Square Toe BootMICHAEL Michael Kors Marilyn Medium SatchelOscar de la Renta Goldtone & Glass Crystal Drop Earrings

Dresses to wear leggings with - Nancy in a gray sweater dress | 40plusstyle.com

Nancy @nancysstyle above (read her style interview here) wears her sweater dress with sneakers and a classic moto jacket. You can get the same look with either leggings or opaque tights.

Check out this similar sweater dress, moto jacket, leggings and sneakers.

Blazer dress

For an evening look, choose a glamorous blazer dress to go with your leggings. Choose coated or leather-look leggings to ensure your outfit has the right level of formality for dinner or drinks.

Blazer dress and leather leggings | 40plusstyle.com

Karen Millen Structured Crepe Belted Blazer Mini DressSpanx Faux Leather LeggingsNaturalizer Wrenley Square Toe BootMICHAEL Michael Kors Marilyn Medium SatchelKenneth Jay Lane 14K Gold-Plated & Faux Emerald Glass Stone Toggle Necklace

Wrap dress

A wrap dress of any length is a great option to go with your leggings. Wear a silky style for evening. Or, for daywear when it’s cool, you can add a turtleneck under your wrap dress and team with leggings and boots.

Wrap dress and leather leggings | 40plusstyle.com

Halston Kiko Draped Long-Sleeve Jersey MinidressSpanx Faux Leather LeggingsTory Burch Reva Leather Clutch-On-ChainShashi Shashi Lynx 14K Gold-Plated Hoop Earrings

White dress

A white dress goes with absolutely everything, including your leggings. We love the shirt-style dress (below). Team with neutral accessories or add a bright color like red.

White dress and leggings | 40plusstyle.com

Toccin Cotton Poplin Tie-Front ShirtdressZella Live In High Waist LeggingsNaturalizer Wrenley Square Toe BootMICHAEL Michael Kors Marilyn Medium SatchelOscar de la Renta Goldtone & Glass Crystal Drop Earrings

Dresses to wear sweaters with - Greetje matches her dress to her boots | 40plusstyle.com

Greetje @no_fear_of_fashion above (read her style interview here) matches her dress to her boots and wears leggings underneath. We love the pop of color she adds with her bag.

Check out these dresses from Treasure & Bond and Amazon that you can wear with this similar pair of leggings, boots, handbag and earrings.

Maxi dress and leggings

A maxi dress can be tricky to wear with leggings unless you’re just adding your leggings for warmth, of course, and you don’t necessarily want them to be seen. Choosing a long shirtdress means you can unbutton your dress from the hem to show off as much of your leggings as you want to.

Maxi dress and leggings | 40plusstyle.com

Alice + Olivia Alice + Olivia X Basquiat Chassidy Belted ShirtdressZella Live In High Waist LeggingsDolce Vita Nadav Ballet FlatTAKEASY Genuine Leather Italian ToteShashi Shashi Lynx 14K Gold-Plated Hoop Earrings

Your dress and leggings outfits together in one capsule

Below, you can see the outfits from above together in one capsule. You can easily wear any of the leggings with any of the dresses.

Dresses and leggings capsule wardrobe | 40plusstyle.com

Continue reading:

  1. How To Wear Leggings Over 40 – A Complete Guide With The Best Leggings And Tops And Shoes To Wear With Them
  2. How To Wear Tunics Or Short Dresses With Pants
  3. The Best Pants And Skirts To Fit And Hide Your Belly

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Dresses to wear leggings with: 9 ways to wear your dresses with leggings | 40plusstyle.com

Feature image by Jess @elegantlydressedandstylish

Sylvia

Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. She is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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