How to Wear a Maxi Skirt after 50

How to Wear a Maxi Skirt after 50
Not sure how to rock a maxi skirt at 50? This articles gives you the exact formula to use to look chic in your maxi skirt. Read to find out.

When I think about maxi skirts for over 50 women, what comes to mind is those Carolina Herrera long flowy skirts paired with a crisp shirt, jewelry, and open sandals. It’s fair to say, however, that the 50 to 60-year-old woman today looks nothing like her age. They look like Jennifer Lopez, Halle Berry, and Jamie Lee Curtis who is well in her sixties.

This means they can rock any style like a 30-year-old, especially a maxi skirt. Nevertheless, styling a maxi skirt in your 50s requires creativity- a crop top just won’t cut it anymore. At this age, you want to dress appropriately whilst also trying not to look frumpy. The wrong maxi skirt, paired with the wrong top or worn wrongly, can make you look way older than you are.

Thankfully, there are many ways to look effortlessly chic and youthful in a maxi skirt without showing too much skin or wearing those dated long skirts that make you feel like your mother.

But first…

Rules for Wearing a Maxi Skirt after 50

Stick to flowy skirts

One way to avoid looking frumpy and inappropriate at 50 is wearing skirts with a bit of flow to them but not too loose. The Carolina Herrera long skirts hit that mark perfectly. However, pleated, tiered, and wrap-style maxi skirts are even better because they are light and don’t resemble a ball gown.

Define the waist

I have seen ladies wearing a loose t-shirt over a maxi skirt, and it’s one of the worst looks in the world. The secret to making a maxi skirt look cool is letting all of it show, starting from the waist. Most long A-line skirts have a waistband that already defines your waist, and you should show it off. If it doesn’t, a belt is a nice way to achieve the same look. But since not all long skirts look good with a belt, you can define the waist with your top by letting it stop right above the skirt. A cropped jacket also does this well, whether it’s a denim or mojo jacket.


Lastly, accessorize the hell out of that outfit. Maxi skirts are essentially a bohemian style, meaning accessories are a must. Hats, sunnies, scarfs, and tons of jewelry are all allowed here. That said, choose your jewelry and accessories depending on the occasion.

Long Skirt Outfits for Over 50 Women

A-line Maxi Skirt and Crisp Shirt

Yes, we would not discuss long skirts for over 50 women without starting with this popular style. The Carolina Herrera A-line maxi skirt and the likes should be a wardrobe staple because you can wear it to many occasions and look like a queen. And though there are many ways to style this skirt, a crisp button-down shirt is the partner that keeps on giving.

For formal occasions or semi-formal events, tuck in a crisp white shirt and pair the look with stiletto heels or nude pumps. You can also add a colorful belt to draw attention to the waist.

For casual wear, use the two sides of the shirt to make a knot on the waist, right above where the skirt starts. Fold back the sleeves to kick up the casual feel and finish it with flat open shoes. You can use any plain shirt here, even a denim button-down shirt, so it doesn’t have to be white.

Floral Maxi Skirt with a Denim jacket

There’s something about a floral maxi skirt that brings back youthfulness. Older women can actually pull off floral skirts better than youngsters. All you need is a plain top like black or white and a denim jacket. With minimal jewelry, a pair of statement sunnies and open sandals, you will be the youngest looking 50 year old in the area.

Pleated Maxi and a White Tee

A pleated maxi skirt is one of the classiest things a woman can own. It’s great for work, special occasions, and even a casual day with friends. Pair this with a white/black t-shirt, a pair of stilettos, or high pumps, and throw a denim/leather jacket on your shoulders. It doesn’t get more elegant than that.

You can also switch the t-shirt with an elegant chiffon blouse (choose the sleeve length depending on the weather and occasion) for a more lady-like look. Add a belt to this, a classy handbag, and sunnies, and you are good to go.

A pleated maxi skirt also goes amazingly well with a crisp white button-down shirt tucked in, and then finished with a belt. Wear high heel pumps and a clutch to tie everything together.

Flowy Maxi Skirt and a Top

Older women tend to stay away from flowy maxi skirts because many of them make you look frumpy. There is a way around this however as long as you apply the rules we outlined above. My favorite look is wearing the skirt with a long-sleeved top tucked in, and high open shoes or flats. Also, try to find a skirt with its own belt or accessorize with a wide belt.

Another great look is to pair the flowy skirt with a plain tee tucked in and then a denim jacket and a scarf around your neck.

Wrap Maxi Skirt

A wrap maxi skirt is the most versatile piece, and women over 50 can rock it in different ways. What you need to know is that you cannot wear this skirt like a 20 year old would with boots and a crop top. Instead, pair it with something modest and classy like a button-down shirt or a short sleeve camisole tucked in. Any fitted top, including a t-shirt will go well with a wrap skirt, especially one with pockets or a high-low style.

I recommend open heels for wrap maxi skirts, but white sneakers and wedges look surprisingly good as well.

Tiered Maxi Skirt with Casual Tops

I would be doing a disservice to all my fellow ladies if I failed to mention the famous tiered maxi skirt. It’s light, fashionable and quite versatile. A t-shirt is the first thing I pick while wearing this type of skirt, and accessorize with a scarf and boho jewelry, or throw on a denim jacket if it’s chilly.

A tiered maxi skirt also looks great with a cropped sweater or ruffled tops. Wear stiletto heels for fancy events like weddings or dinner and rock sneakers for casual errands.

Maxi Skirt and Sweater

My final favorite maxi skirt look on older women is with a casual sweater. Choose a sweater that stops at the waist, or tuck in the sides to show off the front part of the skirt. With this casual look, you only need to accessorize with a few jewelry pieces, wear open flats or sneakers and carry a simple bag. It’s a timeless look that you can rock with any style of maxi dress for any occasion. During fall, add a warm scarf around your neck and some gloves.

Can you wear a maxi skirt over 50 without looking frumpy?

Absolutely. Women of all ages can rock a maxi skirt if they style it appropriately. The secret is to define the waist and wear age-appropriate tops and shoes.

What can you wear with a maxi skirt after 50?

T-shirts, button-down shirts and elegant blouses are great options to pair with a maxi skirt after 50. They are elegant, age-appropriate and don’t show off too much skin. You can also throw on a sweater or a cropped jacket over the top.

Lior Shapiro

I love clothes with pockets and dresses, and I think any woman can pull off a good maxi dress.
I believe women's clothes with pockets make the world a better place.