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Are Dresses With Leggings Still In Style? Find Casual Outfit Ideas

Leggings have been in style since the 1960s when this casual piece of clothing played a key role in liberating women’s dressing.

Over the years, leggings have pretty much remained a style staple, although how we wear leggings is very much an indication of the era.

Are Dresses With Leggings Still In Style? Find Casual Outfit Ideas

Nowadays, leggings are often associated with athleisure wear. High-waisted leggings are often paired with crop tops or shirts, for a casually stylish look that shows off the body. But what about leggings under dresses?

Dresses and leggings were once the height of fashion, and although they might not be a catwalk staple, they are a wardrobe must for many women.

In this guide, we’ll discuss if dresses with leggings are still in style, and how to choose the perfect combination of dress and legging. 

Are Dressings With Leggings Still In Fashion?

Dresses with leggings were one of the most fashionable outfit choices you could make in the mid-naughts to the early 2010s.

From casual clothing to business attire and even the occasional catwalk, leggings and dresses seemed like the perfect pairing.

Nowadays, they aren’t quite so ubiquitous. Both dresses and leggings are popular on their own. Dresses never go out of style, and leggings are part of the current athleisure trend.

Together, however, they aren’t the fashion favorite they were just over a decade ago.

When leggings and dresses were at the height of their combined power, people would wear the look throughout the year.

A thick pair of leggings would ensure you could stay warm in your favorite dress over winter. A patterned or translucent pair of leggings add a touch of personality to your summer outfit.

And in spring or fall, leggings with dresses were the perfect solution when you didn’t know what the weather was doing.

Dresses and leggings are still in fashion, despite not being the hottest trend. It’s a timeless and easy look.

When you’re looking for a seasonal outfit — something to wear when it’s not quite warm and not quite cold — dresses and leggings are the obvious choice.

This look is casual but fun and easy to adapt to your own style. For a lot of women, dresses and leggings have become a wardrobe staple, like a pair of jeans and a t-shirt! 

Dressings With Leggings As A Timeless Trend

Some trends come into fashion and then stick around forever. One of those trends is dresses and leggings.

This was once a style that everyone wore. You’d hardly consider going out of the house without a pair of leggings under your dress! 

You might not spot dresses and leggings on the catwalk anymore, but you are likely to see the combination frequently when you’re enjoying a day out.

Dresses and leggings have gone from being a hot trend to a wardrobe staple, making them a style that will never really go away.

So, why are dresses and leggings such a popular choice?

Let’s start with their versatility. There are many types of dresses, and many types of leggings. It’s easy to find a style that works together.

Next, dressing for the weather. We all have those dresses that we love but don’t get enough chances to wear. One day, it’s early September and your dress is perfect for soaking up the sunshine.

A few weeks later and your favorite dress is locked up for the year. 

Or you can save your dress from the back of the wardrobe by wearing it with a pair of leggings! Leggings add warmth quickly, and extra thick leggings allow you to wear your dress even in the dead of winter.

Finally, this is a super practical combination.

We’ve all experienced that moment when you’re out and about in a dress, having a good time, only to suddenly feel a cool breeze and the realization that you’re sharing slightly more than you want to share!

With leggings underneath your dress, you can move about freely, with no fear of exposure.

How To Style Dresses With Leggings

The single most important thing to remember when pairing dresses and leggings is that the leggings have to fit properly!

Avoid anything loose or baggy. Loose leggings are a little too reminiscent of the infamous jeans under dresses look, and that style has not made a comeback!

We also recommend being very sparing with patterns. Bright and patterned leggings can be fun, but under a dress, they tend to cut the body up. Instead of creating a nice, easy line, it will look like you’ve accidentally worn two different outfits.

Patterned leggings can work under dresses, but we recommend keeping the pattern simple and toning down the dress.

Black leggings are the most versatile choice, but be careful if you’re styling them with a black dress.

If the shades are slightly off, it can look like a total clash. But black leggings and a patterned dress are a classic combination, and easy to get right.

For length, we recommend dresses that finish above the knee. Leggings add a lot of fabric to your lower half, and when you wear a longer dress, it can all be a bit too much. 

Finally, what shoes should you wear? There is room to play with your shoe choices, but it’s hard to go wrong with ballet flats.

Sneakers can also work, and boots are nearly always a good idea (unless you’re wearing Capri leggings). 

Dresses With Leggings Outfit Suggestions

Dresses and leggings can often be mixed and matched to create your perfect outfit, especially if you prefer to buy your leggings in classic black.

But if you’re struggling to imagine how to style the look, we’ve put together some outfit suggestions. 

Each outfit features a dress and a pair of leggings (and we’ve snuck in some shoe suggestions as well). These are simple yet stylish looks, perfect for casual occasions but with a flare of personality.

Outfit 1: Tunic

Amoretu Tunic V Neck Dress

Amoretu Women V Neck Maternity Dress Bishop Long Sleeves Tunic Dresses Plaid S

We love tunic-style dresses as a pairing for leggings. The loose fit and casual style balance the skintight leggings perfectly, and the little extra coverage from the leggings allows you to move freely in the flowing skirt. 

When choosing a tunic dress to wear with leggings, you have to be careful with the balance of fabric. That’s why we love this Amoretu V-neck swing dress.

The slight V-neck contrasts with the long sleeves to keep the dress casual. Finishing above the knees, the dress is highly versatile for seasonal wear.

A tiered tunic style has a fit and flare finish which is ideal for the heavier coverage of leggings. The dress is fitted at the chest, before flaring out below the bust.

The tiered and pleated finish gives the dress a natural movement that’s flattering for all shapes and sizes.

The Amoretu V-neck swing dress comes in a variety of patterns and colors. We’re big fans of the black and white plaid, but really, any of these prints could be worn with leggings!

It’s the shape of the dress that makes it so good!

No Nonsense Women’s Cotton Leggings

No Nonsense Womens Cotton Leggings Black, L

The easiest leggings to wear under dresses are full-length black leggings. This pair from No Nonsense is a comfortable (and affordable) choice and will look excellent with a tunic dress.

Made from a blend of cotton, polyester, and spandex, the No Nonsense leggings have a tight fit that sticks to your curves without getting baggy.

This helps create a long line without wrinkles, so your legs look longer. The cotton-rich fabric provides no-show coverage.

Full-length leggings are one of the most adaptable clothing choices. They can be worn with a shirt or with a dress, for a trip to the store or a night out with the girls. 

You can also experiment with your shoe choice! Full-length leggings (especially those with good coverage) are essentially pants, so they can be worn with sneakers, flats, heels, and boots.

When pairing with a tunic dress, we recommend either a pair of flats or boots, depending on the weather.

Outfit 2: Sweater Dress

ANRABESS Crew Neck Cable Knit Sweater Dress

ANRABESS Women's Loose Crewneck Oversize Sweater Dress 2023 Fall Trendy Long Sleeve Baggy Loose Mini Short Dress Slouchy Chunky Cable Knit Tunic Sweaters 412baixing-M Beige

A little more form-fitting than a tunic dress, the sweater dress is another wardrobe staple that pairs well with leggings. 

Our favorite sweater dress is the ANRABESS crew neck cable knit sweater dress. The chunky knit and looser fit give the dress a casual appeal, while the short length prevents it from becoming a blanket!

It’s ideal for chilly fall days, and you can keep wearing the dress throughout winter with the addition of a cozy coat.

We’ve chosen the classic beige, but the ANRABESS sweater dress is available in a range of colors.

A ribbed hemline and cuffs give some shape to the slouchy dress, and we love the way the lighter color picks out these details.

The simple beige also creates an attractive contrast with the black of the leggings. But feel free to experiment with color! Dark greens and reds are particularly good for fall dressing.

Finish the look with a knitted beanie and a cross-body bag, for easy seasonal dressing.

Hi Clasmix Fleece-Lined Winter Leggings

Women's Fleece Lined Leggings Thermal High Waist Tummy Control Yoga Pants Winter Slimming Workout Running Pants (Black, Small-Medium)

Fleece-lined leggings are great for keeping you cozy in the winter. However, it can be harder to get the fit right with these thicker leggings.

Check the sizing chart closely when choosing your leggings, to make sure they’ll offer that skin-tight finish. 

Fleece-lined leggings will ensure you stay warm even in a mini sweater dress. The thicker build of the leggings ensures they’re opaque, so you don’t have to worry about anything showing through.

There are many styles and brands of fleece-lined leggings available, but we like this tummy control pair from Hi Clasmix.

The sweater dress has a slightly tighter fit, so tummy control helps keep everything tucked in, creating a smooth line under your dress. 

To avoid the awkward ankle gap that you find with fleece leggings, wear this outfit with a pair of boots. They’ll keep you warm, and mask any loose lines from your leggings. 

Outfit 3: Denim

Zilcremo Denim Shirt Dress

Zilcremo Women Denim Shirt Dresses Long Sleeve Distressed Jean Dress Button Down Casual Tunic Top Lightblue S

No outfit says stylish yet casual quite as easily as the shirt dress. With an oversized fit and a flattering hang, the shirt dress says you just threw any old outfit on, and yet you still managed to look fabulous.

Denim is always a fashionable fabric, but it’s particularly on trend right now. Light blue denim is fantastic for summer and spring dressing, but we love the look of darker denim in fall and winter.

Thankfully, the Zilcremo denim shirt dress is available in a range of colors!

The distressed hemline and cuffs add to the laid-back feel of this simple garment. Finishing above the knee, the breathable material can be worn year-round and dressed up or down depending on what you’re doing.

Not so keen on the shapeless look? Add a belt to cinch in the waist and transform the fit. 

Hanes High Waisted Capri Leggings

Hanes Women's Stretch Jersey Capri, Black, Large

Capri leggings are cropped, finishing on the calf between the knee and the ankle.

Capri leggings are super practical, as they’re less warm than full-length leggings, and it’s easier to get a skintight fit when you don’t have to consider the ankle.

However, when you’re pairing dresses and leggings, the Capri cut does present some challenges. It’s a very casual look — sometimes a little too casual! So, you want to be sure your dress matches the vibe while adding some polish.

That’s why we love the combo of a denim shirt dress and Capri leggings. The structure of the denim contrasts the casual stretch of the leggings.

When it comes to shoes, we recommend leaning into the casual style. Sneakers and ballet flats are comfortable and work with the cropped length of the leggings.

You can try a pair of heels, but be careful! This can come across as dated. Boots are also best avoided, as you risk the awkward gap between the end of the leggings and the start of your shoes.

Final Thoughts

Dresses and leggings might not be the style icons they once were, but this look is the type that never goes out of fashion. How do you like to wear your dresses and leggings?

Jenna Reign
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Last update on 2023-09-29 / Affiliate links / Images from Amazon Product Advertising API