How to Wear a Sweater Dress with Leggings

Have you ever been clothes shopping and come across a fabulous sweater dress, only to discover that it’s a little too short? If you’re in your twenties or thirties, flaunting your mini sweater dress with bare legs or thigh-high boots might work, but there’s a fine line when it comes to looking fabulous or desperate at midlife and beyond. So, what do you think is the solution?

Pantyhose may come to mind, but they tend to be too light and sheer for the weight and texture of a knit sweater dress. Opaque or semi-opaque tights can work, but if you prefer a more creative, artsy vibe, then leggings are your answer. Here’s how to master the art of pairing a sweater dress with leggings.


Start with the Right Leggings

Long. Short, thick, thin, seamed, shiny, opaque, colored. Patterned… there are so many types of leggings, and it can feel overwhelming to know what kind to wear with a sweater dress,  but it doesn’t have to be.

My advice to keep things modern and classy would be to stick to long, opaque black leggings that end just above the ankle, medium weight, with no or minimum shine. If leggings are too thin or not opaque,  they look like stockings, and if the sweater dress is too short, it seems like you forgot your pants. Spanx makes a great seamless legging with a high waist and tummy control, which is always helpful.

Black is the best color because it goes with anything and will let the dress take center stage. And after all, it is about the dress. Leggings are an accessory.

This is not to say that other dark shades like brown, green, and plum can’t work, too. However, I find that brightly colored leggings with a dress, i.e., red leggings with red, blue, and green print tops, start looking like you are the court jester. They’re not modern.

Another chic option- is faux leather leggings-  These can look very hip with a sweater dress. The texture-on-texture look is a gorgeous mix.


Explore Sweater Dress Styles

Just because it’s a sweater dress doesn’t mean it will look good with leggings. Two types that work well are:

Tunic style sweater dress

Long straight, often with slits at the sides or big front pockets. A tunic sweater can have a round neck, boat neck, cowl neck, or turtleneck. It doesn’t matter, so long as it hangs straight, or skims your body but is not tight. This is a great style for gals with thick midlife middle.

A chunky, oversized sweater

These dresses resemble oversized sweaters. They often taper slightly towards the hem and end at the top or middle of the thighs.



A few sweater dress styles to avoid: 

  • Fit and flare sweater dresses- A skater-style sweater dress is too broad and full over leggings. It is too much like an actual dress, which should look more like a tunic or oversized sweater.
  • Sweater dresses that are too long. Sweater dresses that end below the knee or midi and maxi sweater dresses don’t look as good with leggings. You barely see any of the leggings.
  • A-line sweater dresses that flare out into a triangle shape and are loose and flowy. The wide triangle shapes widen you at the hips and thighs and are also dated.
  • Tight-fitting sweater dresses are not flattering over leggings either. You can look stuffed into your clothes. Slightly wider over skinny is the silhouette you should be after when wearing a sweater dress with leggings.


Leather Leggings Outfit l Brown leggings, brown sweater dress, booties l styled by Fabulous After 40

Elevate with the Right Footwear

Boots, ankle or tall, look fantastic with leggings and a sweater dress. Leather work but suede is always fabulous for a rich textured look.

As for color, the closer they are to the color of your leggings, the longer your legs will look,  A contrasting color breaks up the line and gives you outfit a more casual appaearacne.. Tall, flat, or low chunky-heel riding boots look excellent with a sweater dress and leggings, giving your outfit an adventurous or equestrian look. (More boots with sweater dresses here.)

Prefer shoes? You can wear a pair of slip-on flat mules, which can be very chic. Ballet flats also work well and look cute with leggings that end at the ankles.


Search For Exciting Ways to Style Sweater Dresses with Leggings

Accessories go a long way in tying this whole look together. Why not:

  • Belt your sweater dress if it is a straight tunic style
  • Wear an oversized scarf with a sweater dress + leggings. The chunkier and less refined the sweater scarf, the more rustic the scarf.
  • Push up the sleeves on your sweater dress for a more casual, sporty look in keeping with the simple leggings.

Own the Look

The key to wearing a sweater dress with leggings or any clothing with leggings is to try it, see how it looks and pay attention to how you feel. Does your outfit look like two unrelated pieces, or is it one continuous creative look? Does wearing your sweater dress with leggings make you feel awkward or stylish? Ask yourself these things and be honest to know whether you have nailed the sweater dress over the leggings look!

Do you like wearing sweater dresses with leggings? Let me know and post a photo in my private Facebook group- The Fabulous After 40 Dressing Room. You can sign up here.

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One thought on “How to Wear a Sweater Dress with Leggings

  1. I already had a mind to style my sweater dress in this manner with leggings underneath, so THANK YOU for confirming that it was a good idea:)

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