How to Wear a Sweater Dress with Leggings

Have you ever passed on a fabulous sweater dress because it just felt too short to wear on its own? I know the feeling. Some of those cropped styles look adorable on the hanger, but once you try them on, they can feel a little skimpy—even with opaque tights. A short sweater dress can easily look a bit off once you’re over 40, 50, or 60

Okay, but don’t give up just yet—there’s an easy fix for this. Treat your short sweater dress like a tunic and wear it with leggings. It’s a clever way to create an intentional and chic look. Here’s how to pull it off so you look polished, not like a preschooler.

How to Wear a Sweater Dress with Leggings

Start with the Right Leggings

With so many types of leggings available, it can be challenging to determine which one works best with a sweater dress. Let’s break it down.

Black Leggings

For a modern, classy look, opt for long, opaque leggings that end just above the ankle. Pick a medium-weight fabric with little to no shine—too thin looks like stockings, too thick like pants, too shiny competes with your dress.

High-waist Spanx leggings are a favorite for their smoothing fit and tummy control. And if you want a trendier twist, stirrup leggings are back and look really modern with a sweaterdress.

Black is always best because it pairs with everything and lets the dress stand out. You can try dark neutrals like brown, green, or plum, but skip bright or patterned styles—they can make the outfit look busy or cheap.

Faux Leather Leggings:
These are another chic option. The sleek, slightly edgy texture contrasts beautifully with a soft knit dress for a rich, modern look. Spanx has the best!

Split-Hem Leggings:
This newer style features a small slit at the front or side hem, giving the illusion of slim pants. They’re a fun, fashion-forward way to elevate your outfit.

Jeggings:
Jean-style leggings can also work, especially with casual sweater dresses. Just make sure they’re not too heavy or bulky—they should balance the softness of the knit, not weigh it down, like these from Lysse.

Shop the look

The Best Sweater Dress Styles to Wear with Leggings

Just because it’s called a sweater dress doesn’t mean it automatically looks great with leggings. The most flattering and modern pairings usually come from these styles:

1. Tunic-Style Sweater Dress
This is hands-down the easiest style to pull off. A straight-up and down tunic-length sweater dress (sometimes with subtle side slits) gently skims your figure without clinging. It shouldn’t fit like a body-con dress or adhere to the hem. It’s especially flattering if you want to downplay a thick waist.

2. Chunky, Oversized Sweater Dress
Relaxed, cozy, and effortlessly cool—this style feels like wrapping yourself in your favorite blanket but looks a whole lot more polished. These sweater dresses have a more rounded shape and taper slightly toward the hem ending between mid thigh and above the knee. Pair it with sleek leggings and knee-high or ankle boots to balance the volume up top.

Shop Sweaterdresses for Leggings

3. Cardigan Sweater Dress
An oversized cardigan sweater dress is cool to pair with leggings. You can even layer something underneath the cardigan, like a tank, add a belt, or leave it as is. This is a snuggly, modern look paired with leggings.

4. Cowl-Neck or Funnel-Neck Sweater Dress
These necklines are perfect for softening your look and drawing attention upward toward your face. They add a touch of sophistication without the constriction of a turtleneck—ideal for women who love warmth but not bulk.

Style Tip:
Aim for a hemline that hits mid-thigh to just above the knee. It’s the most flattering length over leggings, keeping your proportions sleek and balanced.

Sweater Dress Styles to Avoid: 

• Fit-and-flare -A skater-style sweater dress is too broad and full over leggings. It looks too much like an actual dress, which should resemble a tunic or oversized sweater.
• Very Long  – Sweater dresses that end below the knee or midi; maxi sweater dresses don’t look as good with leggings. You barely see any of the leggings.
• Wide A-line   sweaterdresses that flare out into a stiff or voluminous triangle shape. The wide, triangular shape accentuates your hips and thighs, but looks dated.
• Tight-fitting body-con  sweaterdresses are also unflattering over leggings. They can make you look stuffed into your clothes and outdated. Instead, go for a slightly wider silhouette to complement the slim fit of the leggings.

The Right Shoes and Boots to Elevate Your Sweaterdress with Leggings

The right shoes can completely transform this look. Whether you prefer polished and classic or casual and edgy, the key is to maintain balanced proportions and an intentional vibe.

Boots
Boots and leggings are a match made in heaven!

Tall boots with a modern square toe, ankle boots,all work beautifully. Both leather and suede are great choices, but suede adds a rich, textured finish that feels especially luxe in fall and winter.

For a timeless combo, try riding boots with your sweater dress and leggings. The look has a chic, equestrian vibe that never goes out of style.

If you prefer something trendier, opt for lug-sole boots to add a cool, modern edge to the outfit.

(See also: Shoes and Boots to Wear with Dresses)

Flats & Sneakers
Slip-on mules are effortlessly chic, while ballet flats—especially the newer Mary Jane styles—add a feminine touch and pair nicely with ankle-length leggings.

Loafers offer polish, and fashion sneakers add a relaxed, sporty twist to the outfit that still looks intentional.

Color Tip:
If you want to elongate your legs, keep your shoes or boots the same color as your leggings. A contrast color breaks up the line and gives your outfit a more casual, laid-back look.

Simple Ways to Wear a Sweaterdress with Leggings

• Belt your sweater dress: Define your waist and give a loose dress a more flattering shape.
• Add an oversized scarf: A chunky, textured scarf adds warmth and personality. The less refined it looks, the more rustic and cozy the vibe.
• Push up your sleeves: Rolling or scrunching the sleeves of your sweater dress instantly makes the look more casual and sporty—a great contrast to sleek leggings.

Own the Look

The key to wearing a sweater dress with leggings, or any other dress with leggings, is to try it on, see how it looks, and pay attention to how you feel.

Does your outfit look like two unrelated pieces, or like one creative look? Does wearing your sweater dress with leggings make you feel awkward or stylish? Ask yourself these questions and be honest to determine if you’ve nailed the sweater dress over 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.

Meet the author

Deborah Boland

Deborah, a former Fashion & Lifestyle TV host and Image Consultant, understands the style challenges women face in their 40s, 50s, and 60s. As the founder of Fabulous After 40, she helps women tweak their chic and embrace fashion with confidence—so they always look and feel amazing.

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