What Kind of Dress to Wear Over Leggings

Leggings can be an extremely comfortable piece of clothing to wear throughout the year. Below, you will all the tips you need on how to wear leggings over 40 as well as the best leggings to choose for your leggings outfits.

What are leggings?

Before we get onto how to wear leggings, what exactly are they? Leggings are thicker than tights so they are nice and warm and give good coverage for your legs.

Generally skin tight, leggings tend to end at your mid calf or ankle. They're stretchy so you don't need any fastenings to get into them. And, depending on the style and material, you can wear leggings for everything from exercising to a night out.

So, exactly how should you wear leggings so they also look good? And which are the best leggings to buy?

In this updated article with new shopping options, I will give you lots of guidelines on how to wear leggings over 40, 50 and beyond and where you can buy the best leggings online.

You will also find a capsule wardrobe of the best leggings as well as tops, sweaters, coats, dresses, shoes and accessories to wear with them.

How to wear leggings so you look stylish?

Leggings are a great transitional option for spring and summer as you can wear underneath dresses or tunics, meaning you can continue wearing your favorite summer dresses even if the weather is still a little cool.

Meanwhile, for winter, you can wear your leggings with sweaters and boots.

In my opinion, you should not wear leggings like normal trousers.

I would not do that at any age, but it certainly does not look very classy when you are over 40.

As they reveal all curves of your legs, I feel it is much nicer to wear leggings as a supportive element for the rest of your clothes, rather than as a main garment.

Abbey (above) opts for a pair of edgy leather-look leggings and teams them with boots and an on-trend cape.

Check out this similar roll neck top, cape, leggings, booties and necklace to recreate her outfit.

Also find out our top picks for the best tummy control leggings.

What are the best leggings to buy?

You will want to make sure that your leggings are thick enough and have a good stretch, yet are still firm enough to give your legs a great shape.

For that reason, it's wise to invest in a good pair.

Ponte leggings (a hybrid of leggings and pants) are also a good choice.

If you like even thicker leggings, you may consider jeggings or elasticated skinny jeans. I would steer clear of shiny or sheer leggings.

Leather or faux leather leggings are great for an edgier look and can be easily 'softened' with a silk tunic.

Melanie (above) wears an all-black leggings look and adds extra interest with her oversized jewelry.

Get her look with this similar dress, leggings, booties and earrings.

If the weather is still cold where you are, you can read our article on the best winter leggings for women over 40.

Some great brands for leggings include:

It can be tricky to find a pair of leggings which give great coverage, aren't see-thru and don't lose their shape. So before looking at how to wear your leggings, below are some of my favorite brands as well as recommendations from 40+ Style readers.

1. Zella live-in leggings

Zella live-in leggings have consistently good reviews. -These look just as good for everyday wear or for a workout.

Zella high waist leggings

2. Satina high-waisted leggings

Satina leggings come in several colors so you could always opt for a softer hue for summer if you already have black leggings in your closet or a winter shade like navy or burgundy. They have a high waist (making them perfect for hiding your belly)

Satina high waisted leggings

3. Stella Carakasi

Have you discovered the Stella Carakasi brand yet? These leggings are my personal favorites. I own their second nature capris and ready to wear leggings.

They are firm and high-wasted, thick but not too thick and they keep their color and stretch, wash after wash.

You'll also see I often wear asymmetrical tops from the same brand. Take a look at the best asymmetrical tops and dresses.

Second Nature capris – Ready to Wear leggings

4. NYDJ

NYDJ are well known for creating jeans for curves rather than for teenage girls. They also have a range of flattering leggings.

NYDJ pinstripe ponte leggings

5. Eileen Fisher

Eileen Fisher is well known for classic and timeless styles that you can wear year-upon-year. So it's no surprise, you'll find the brand features some classic leggings and jeggings.

Eileen Fisher velvet knit leggings

5. Lyssé

Lyssé prides itself on offering foundational wardrobe essentials. After all, every great wardrobe starts with good foundations! You can read more about this idea in how to create the ultimate capsule wardrobe.

Leggings make a good foundation because of their versatility. You can wear under so many different items of clothing in so many different ways. Read on for outfit ideas as well as a capsule wardrobe based on leggings.

Lyssé crop slit denim leggings

6. spanx

Spanx is renowned for shapewear. But, you'll also find some well-fitting leggings among its range.

SPANX faux leather leggings

MORE LEGGINGS TO CHOOSE FROM

Of course, you don't have to limit yourself to the brands above, the below leggings also have fantastic reviews.

Sandra (above) gives inspiration on how to wear your leggings more casually.

Get her look with this similar top, leggings and sneakers.

1. Best leggings for women

When searching for the best leggings for women, another good option to choose are the 90 degree leggings from Amazon (below) which have thousands of good reviews from women who say they prefer them over bigger brands.

90 Degree By Reflex high waist tummy control shape wear

2. Best Amazon leggings

Another good choice from Amazon are the Heathyoga leggings (below) which are perfect for working out. One reviewer even described them as the best leggings she has ever owned.

Heathyoga yoga leggings

3. Best high waisted leggings

Leggings which fall down or which leave you at risk of flashing your underwear are definitely not flattering. So, to make sure everything is tucked in, opt for a pair of high-waisted leggings like the ones from Fullsoft (below) which also feature tummy tuck technology.

FULLSOFT tummy control leggings

Jacqueline (above) looks chic, casual and ready for a workout or a walk in her leggings and sneakers.

Recreate her outfit with this similar top, leggings and sneakers.

4. Best plus size leggings

If you're looking for the perfect pair of plus size leggings, the stretch jersey leggings (below) from Just My Size may be the answer. Reviewers say they are curve-hugging and stay put without being uncomfortable.

Just My Size Women plus size jersey leggings

5. Most comfortable leggings

When looking for comfy leggings, how they stretch is important. The leggings (below) from Tnnzeet have four-way stretch, and they come in packs of three, making them good value.

TNNZEET high waisted leggings

6. Best faux leather leggings

If you want to add a little edginess to your outfit, a pair of leather or faux leather leggings is a good option. You could wear casually with a long sweater, or for evening with a tunic top or dress.

Retro Gong faux leather leggings

7. Best cotton leggings

Cotton is a good choice for so many items of clothing, and leggings are no exception. If you're looking at leggings for working out, cotton can keep moisture against your body rather than wicking it away.

But cotton leggings can be ideal for everyday wear.

Rachel (above) teams her leggings with a sweater and knee-high boots for a casual, yet stylish outfit.

Get her look with this similar sweater, leggings, knee high boots and crossbody bag.

HUE cotton ultra leggings

8. Good leggings

When choosing leggings, quality is important. After all, you don't want everyone to be able to see your underwear and every lump and bump.

The Colorfulkoala leggings (below) are available in a huge range of colors and have good reviews from women who say they are the best quality to be found at their price point.

Colorfulkoala high waisted lull-length leggings

9. Best jeggings for women

A pair of jeggings are another good style to think about. These are great for wearing casually with sweaters and boots.

No Nonsense denim leggings

10. Best leggings with pockets

If you're exercising or out for a walk, you might prefer to choose a pair of leggings you can fit your phone in like the leggings from IUGA (below).

IUGA yoga pants with pockets

11. Best cheap leggings

Unless you have an unlimited clothing budget, you may be looking at good leggings on a budget. The Muk Luks leggings (below) are well-priced but have good reviews from women who say they are amazing for the price point.

MUK LUKS fleece leggings

12. Best leather leggings

Lynne (above) looks fabulous in her leather leggings worn with sparkly boots.

Recreate her outfit with this similar blouse, leggings and booties.

Vince leather zip leggings

13. Control top leggings

There are plenty of leggings which don't just look stylish, but can also help to smooth out your silhouette. The Dragon Fit tummy control leggings (below) have good reviews on Amazon from women who say they comfortably hold everything in without feeling restrictive.

Dragon Fit tummy control high waist leggings

What to consider when choosing leggings

As you can see, the choice of leggings is endless. So now that you're thinking about the legging brands to look for, what else should you consider?

Length

Just as with skirt hem lengths, or the arm lengths on your tops, there are a number of legging lengths you could opt for.

Your leggings could end just below your knees, at your calves or ankles or they could be full-length.

Choose ankle or full length to tuck into booties, or a shorter length for your summer sandals.

For an extra flattering look, opt for leggings which hit your legs at their slimmest point.

Tanasha (above) looks stunning in her burgundy leggings. You'll see she wears with boots of a similar color, which makes her legs look even longer than they are.

Recreate her outfit with this similar top, coat, leggings and booties.

Fabric

By their very nature, leggings come in stretchy fabric so you can pull them on without any fasteners. Usually, they have a mix of lycra and cotton, but you could choose from all sorts of materials such as a leather look or denim depending on whether you are opting for a casual or evening look.

Caroline wears her leggings under her dress.

Check out this similar denim dress, jacket, leggings, belt and boots.

Color

Black leggings are clearly a complete classic that will go with everything you own. They are the perfect addition to a capsule wardrobe.

But you could also think about white for summer, or add some color or pattern to your outfit. However, if you do opt for colored leggings, you may wish to keep the rest of your outfit more subtle.

Racheal (above) chooses to create a stylish monochrome look with her leggings.

Get her look with this similar shirt, sweater vest, leggings and booties.

What to wear with leggings?

So, now that you have a few ideas for the best legging brands to choose and other factors to consider, what should you wear with them?

Leggings look best with longer tops and tunics. Short dresses can also look great with leggings.

So, if you do own a shorter dress that you have pushed to the back of your wardrobe, you could always try it with leggings before you decide to donate it.

Leggings work best when they act as a base for your other clothes. If you want to wear shorter tops I would recommend wearing jeans and other pants.

Find out some of our top recommendation for jeans.

The best tunics to wear with leggings

Judith (above) wears a fun tunic sweater.

Check out this similar long sweater tunic, leggings and boots to steal her look.

Leggings look better with longer tops. You still want to make sure that you create enough structure in your outfit though.

You can do that through the right tunics and longer asymmetrical tops.

The latter especially create flattering vertical lines and add a bit of extra style to your look.

LARACE flowy tunic top – All in Favor tunic – COS sweater vest – Miusey cowl neck tunic top

Wear leggings with a long shirt

Because a long shirt covers up your bottom and thighs, you can afford to go a little bit edgy with your leggings. You could opt for a pair in leather or faux leather.

All of these shirts (below) would look great with a pair of faux leather or coated leggings.

Krista (above) pairs her coated leggings with a check skirt.

Get her look with this similar plaid shirt, leggings and sneakers.

Ted Baker London peplum shirt – H&M patterned blouse – Donna Karan print tunic – Treasure & Bond button-up tunic

Short dresses to wear over leggings

Instead of designated tunics you can also wear a short dress over your leggings.

An asymmetrical dress or draped dress will make a real statement.

If you have pushed a shorter dress to the back of your closet before you don't feel confident about the length, it could be time to get it back out and try it with leggings.

Good Luck Gem tie dye cap sleeve dress – Badgley Mischka belted blouson dress – Lilly Pultizer shift dress – Ted Baker London shift minidress

Longer dresses

It can be tricky to wear a longer dress with leggings because you need to think more carefully about the proportions of your outfit. A great way to make sure you get it right is to wear a dress with a slit in it so you show off a little leg (or at least a little legging!).

Katie (above) looks beautiful in her floral dress and leggings.

Check out this similar dress, leggings, coat, booties and sunglasses.

COS wool mix shirt dress – H&M knit dress – H&M wrap dress – COS belted leather dress

Layer your leggings with a cardigan or sweater

Leggings are definitely your friend when it comes to layering.

They look great worn under long tops and ponchos with ankle booties.

If you're heading out for a walk or to run errands, slinging a lightweight coat over a pair of leggings, together with a long-line tunic, can be a stylish option

Or, rather than wearing a coat, as you are likely to be heading into spring, you could try teaming your leggings with a cozy knit?

When choosing a sweater to go with your leggings, opt for a long-line version which will cover up your bottom.

Or, if that is an area of your body you are confident about, you could always wear a pair of skinny jeans and a shorter sweater.

Laura (above) opts for blue leggings to match her winter sweater.

Check out this sweater from Amazon that you can wear with this similar pair of leggings and boots.

Free People sweater tunic – L'AGENCE stripe cardigan – ALLSAINTS tie ruana – Urban Coco drape front open cardigan

Lightweight cover-ups

Given that some of you will be heading into the warmer months, another way to wear your leggings could be with a lighter-weight cover-up.

That way, you can still take advantage of flattering layers while staying cool.

Melissa Odabash tiger stripe cover-up – Nordstrom fringe ruana – ALLSAINTS patterned ruana – Miraclesuit caftan

Leggings look great with jackets and long coats

Long cardigans can create lovely vertical lines which can help to elongate your figure.

But you can always wear a longer coat to keep you warm.

Another idea is to wear a longer top or short dress over your leggings and then to layer a moto or denim jacket over it.

Jenny (above) elevates her leggings outfit with a plaid blazer.

Check out this similar tee, blazer, leggings, sneakers and tote.

Ted Baker London slim fit blazer – BLANKNYC drape front suede jacket – Lock and Love biker jacket – Anne Klein drape front long jacket

In general, your ideal garments to combine with leggings include:

• Tunics
• Asymmetric tops and tunics
• Short dresses
• Knit dresses
• Long knitted sweaters
• Longer asymmetrical pieces
• Long cardigans
• Big wide sweaters
• Sweater dresses

Shoes to wear with leggings

As you will see from all the examples in this article you can wear a wide variety of shoes with your leggings.

I feel that open vamp shoes look the best as they will further lengthen your leg line.

But, with cooler weather, you can definitely wear your leggings with closed toe versions such as booties, sneakers and knee-high boots.

Abi (above) wears tan leggings with her sneakers.

Steal her look with this similar sweater, coat, leggings, sneakers and tote.

Zodiac pointed toe flat – VANELi leather bootie – Bos. & Co. waterproof tall boot – Vionic sneaker

Accessories to wear with leggings

Of course, anything goes when you are choosing accessories to wear with your leggings.

But generally, leggings invite a casual look, so you could opt for scarves and crossbody bags rather than anything too formal.

Joanna (above) chooses a leopard print crossbody bag to go with her leggings.

Check out this similar hoodie, coat, leggings, sneakers and crossbody bag.

Kate Spade New York shoulder bag – Madewell leather tote – Tory Burch nylon crossbody bag – Zando plaid scarf – rag & bone leather belt – Karine Sultan statement necklace – Karine Sultan teardrop earrings

For which body type would leggings be suitable?

If you follow some of the guidelines above, all body types will be able to wear leggings.

If you have very thick calves though I would recommend you wear skinny jeans so the pants skim over your calves and will make them look slimmer. Make sure your leggings don't end at the widest point of your legs.

Wide legged pants are also an option or you could wear leggings with nice knee-high boots.

Leggings can work especially well for the apple body type.

Your long tunic or top covers your belly and the leggings show off your fantastic legs.

You could never tell that Anja does have a tummy from these images (below).

Although women with the pear body shape can wear leggings as well, it is important that they choose a top with sufficient length over them.

If you are self-conscious about your tummy, it's also worth taking a look at how to hide your belly with the right clothes.

How to wear leggings in summer and for travel

In case you live in warmer climes, below are a few travel looks with leggings.

Here is how I wore black and white leggings on holiday. Tunic by Stella Carakasi.

Above is when I wore a white long tunic over a pair of capri leggings.

Leggings with asymmetrical tunics

I especially love asymmetric tunics and tops as they create an interesting silhouette and lengthen you through additional vertical lines.

Here is how I recently wore a super asymmetrical black top with white over-the-knee skinnies and a high / low tunic with very stretchy skinnies.

Also take a look at the best asymmetrical tops and dresses.

What not to wear with leggings over 40

I've spoken a lot about what TO wear with leggings, but what are some of the things to avoid?

• Avoid any tops that are higher than mid-thigh
• Don't wear tops that are too tight
• Avoid animal prints (unless you are opting for skinny jeans instead of leggings) and disco fabrics for your leggings and remember that the classier the top, the better leggings will look.
• The luxury fabric of silk, wool or cashmere will create a great contrast with the comfortable jersey leggings.

What is the ideal length of your leggings

You can never go wrong with full-length leggings. These elongate and will make your legs appear longer.

Ankle-high leggings can also look sexy especially with heels or booties.

If you are short though, mid-calf and short leggings should be worn with caution as they will make you look smaller.

Above is a look with an asymmetrical tunic and draped leggings which are available in many colors.

Another length I like in warmer weather is just below the knee. These Second Nature Capri leggings  from Stella Carakasi (below) are super fab.

Not too thin and very stretchy and comfortable. They are also great for tucking in your tummy.

I have these leggings in various colors and also use them for working out and yoga!

As you may have seen from the images above, it is great to wear a shoe in the same color as your leggings as it elongates your legs even further.

Tall flat boots can work really well with leggings, but short booties and ballet flats can work equally good.

For more info on what kind of shoes to wear with what pants check out this article.

What about jeggings and skinny jeans?

I'm also a big fan of looser fitting leggings, jeggings or skinny jeans.

Above is a look I wore to travel in. Also take a look at travel outfits for women over 40.

These will not show every curve in your legs, but will provide nice vertical lines and make your legs look long and slim.

Depending on the kind of jeggings and skinny jeans you choose, your tops can be shorter for these pants although, just like leggings, they will also look good with longer tops.

They can be a great asset for any wardrobe of women over 40.

Skinny jeans are usually a bit thicker and roomier so can be worn with shorter tops.

Be sure to wear the right underwear though, so there is no clear VPL (visible panty line). (Featured below are myself and Greetje).

Dayle (below) wears a black column outfit with a pair of skinny jeans and adds a pop of color with her scarf.

Below is another look featuring my asymmetrical top.

A capsule wardrobe with 9 ways to wear your leggings

Of course, there are so many ways you could put together the leggings, tops, sweaters, dresses, shoes and accessories in this article to create many, many outfits. But here are 9 outfits to get your started.

Let me know which of these outfits you would wear.

Read our ultimate guide to creating a capsule wardrobe that works best for you.

If you want to make sure, you never miss an article and to get the best tips straight into your inbox as well as a free guide on how to find your style, be sure to subscribe to the weekly newsletter.

I hope you got some more clarity on how to wear leggings! What do you think? Do you like wearing leggings and how do you usually wear leggings?

Continue reading:

1. The Best Tummy ControlJeans To Give You A Smoother Look
2. The Best Pants And Skirts To Fit And Hide Your Belly
3. 14 Sure-Fire Ways To Hide Your Belly With The Right Clothes

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Feature image by Joanna

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