How to Wear a Sweater Dress with Leggings

Have you ever passed on buying a fabulous sweater dress because it was too short?  Cropped sweater dresses may been fine in your 20 and 30’s worn with bare legs or thigh-high boots, but they look a little desperate, even with black, opaque hose at 40, 50, 60.

One way to get around this is to pair a sweater dress with leggings for a modern, artsy look.  Here’s how to master the art of pairing a sweater dress with leggings.

Gray sweaterdress | Leggings | purse | booties |bracelet | earrings

How to Wear 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.

Opaque Black Leggings: To keep things modern and classy, I recommend wearing long, opaque black leggings that end just above the ankle, are medium-weight, and have no or minimal shine. If the 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 great seamless leggings with a high waist and tummy control, which is always helpful.

Black is the best color because it goes with anything and lets the dress take center stage. 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.

Faux Leather Leggings are another chic option. They can look very hip in a sweater dress, and the texture-on-texture look is a gorgeous combination.

Split-hem leggings are interesting. These are leggings with a slit up the front or side which almost make them look like super skinny pants.

Jeggings—Jean leggings can also work, although in some cases, they may look too heavy. You be the judge.

Green Sweater dress | brown booties | bag | belt | earrings

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

Tunic sweaters are long, straight, often with slits at the sides or big patch 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 it’s not tight. This is a great style for gals who want to camouflage a thick midlife middle.

A chunky, oversized sweater

These sweater 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 looks 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.
• Wide A-line sweater dresses that flare out into a stiff or voluminous triangle shape. The wide triangle shape widens you at the hips and thighs and also looks dated.
• Tight-fitting body-con sweater dresses are also unflattering over leggings. They can make you look stuffed into your clothes and outdated. When wearing a sweater dress with leggings, aim for a slightly wider silhouette over skinny leggings.
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  gray sweater dress | leggings | Bag | scarf | loafers | earrings

Elevate with the Right Footwear

Boots with leggings is a match made in heaven!

Boots, ankle or tall to the knee, also look fantastic.  Leather and suede both work, but I prefer suede because it gives your outfit a rich, textured look.

Other boots that work are low-heeled riding boots with a sweater dress and leggings. This classic look gives your outfit an adventurous or equestrian vibe. A more edgy way to style a sweater dress with leggings is to wear them with a lug sole or combat boot. (See more boots with sweater dresses here.)

Do you prefer shoes? Slip-on flat mules are very chic. Ballet flats, especially the new Mary Jane ballet flats,  also work well and look cute with leggings that end at the ankles. Loafers and sneakers are also popular.

As for color, the closer the shoes or boots are to the color of your leggings, the longer your legs will look; a contrasting color breaks up the line and gives your outfit a more casual appearance.

taupe sweater dress | leggings | boots | bag |earrings

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 – Create a waist and a less baggy shape.
• 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 that complements 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? If so, please let me know and post a photo in my private Facebook group, The Fabulous After 40 Dressing Room. You can sign up here.