How to Style Long Skirts

Maxi dresses became popular at the beginning of the century and since then, have just gained in popularity, extending to maxi and long skirts. And looking at this year's fashion trends, it's clear that long skirts aren't going anywhere. But long skirts can feel tough to style. What shoes? What kind of top? Don't worry my friends, I've got you and will share below how to style long skirts in a range of ways that will hopefully work with your personal style aesthetic.

How to Style Long Skirts

Depending on the style of your long skirt, you can follow some of the rules on how to style wide leg pants. However, long skirts come in various fabrics and silhouettes, which can impact how they are styled. Below, I will break down how to style some of the most popular styles of long skirts in a contemporary manner.

How to Style a Long Denim Skirt

Long denim skirts came back in vogue in the past year or two, and with the Americana Chic trend and the popularity of cowboy culture ad vintage style, they aren't going anywhere any time soon.

The most popular style of long denim skirts right now is a straight to slight a-line silhouette, with jeans-like details (zip fly, five pockets, rivets), and often with a front slit for ease of movement. While you can find long denim skirts in various colors, the most stylish option is choosing one with a classic denim wash, like stonewashed denim.

Denim is a stiff fabric, and you want your shoe to be able to handle it. Leather, suede, and canvas are great pairings, as are styles with wood, cork, or block heels. Either the shoe should go up under the skirt hem, or there should be at least an inch or two of leg between it and the shoe.

Style a Long Denim Skirt with Tall Boots

When styling a long denim skirt with tall boots, you will have the best effect with a knee-high boot with a slim shaft but a block heel or strong sole. This will reduce bulk under the skirt and give a clean line.

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An alternative is a cowboy boot, which is a shorter shaft, but still has a strong sole, thicker though lower heel, and a sleek effect. I do not recommend booties or ankle boots as the hemline will conflict with its height.

Style a Long Denim Skirt with Sneakers

Street style fashionistas wear all sorts of sneakers with long denim skirts, but they also have a good concept of proportion and the confidence to be quirky. For the rest of us, I recommend a low-profile sneaker that does not compete with the stiff denim fabric.

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A pair of classic Converse Chuck Taylors is a great choice, especially in a color low-contrast to your skintone. An alternative is the low-top retro-inspired sneakers that are so on trend. This is a great option if you love a colorful shoe.

Style a Long Denim Skirt with Sandals

Just as with boots, you want your sandals to have some oomph and stability to them. Block heels, especially out of cork and wood look great with long denim skirts.

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For a flat sandal, look for one with some heft like Birkenstocks to balance the stiff jean fabric.

How to Style a Long Pleated Skirt

The long pleated skirt became extremely popular a couple of years ago and continues to be a stylish option. While the original style was a calf-length micropleated skirt in everything from silk to faux leather, this season we're also seeing softer pleats, drop waists, kilt-inspired details, and lengths from midi to maxi length.

Long pleated skirts are actually quite versatile when it comes to footwear. Steer from any chunky boots that may catch on the soft layers or affect the fall of the pleats. With ankle boots, a tall shaft will look most modern. Pretty much any kind of sneaker works, though really trim shoes like Keds will make the skirt feel dowdy. Keep spring and summer shoes flat unless you're wearing them to a formal occasion.

There are two ways to make long pleated skirts look modern in 2025: go monochromatic, or go oversized. Here are some way to achieve these looks in an elevated, grown woman manner:

Style a Long Pleated Skirt with Boots

Boots are a great choice to wear with long pleated skirts as it creates a continuous line, and it's a great alternative to pants in the winter. Suede or leather, slouchy or trim, I do recommend choosing a sleeker sole over lug, with the lower the heel the slimmer the toebox.

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Though there is print and multiple colors in this look, it is still very cohesive. Instead of a tucked-in top and short jacket, the blazer is longer, the turtleneck loose (or a faux tuck; instructions at this link). While feeling more comfortable, this looseness also feels more modern.

Style a Long Pleated Skirt with Sneakers

A great way to modernize your long pleated skirt is to pair it with sneakers. Retro-inspired sneakers like current styles of Reebok, Puma, Adidas, and New Balance are great choices, and a way to add a pop of color to your outfit.

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While crew socks have come back in fashion, it is not necessary for you to wear them. If you prefer a no-sock look, that will still look modern.

Style a Long Pleated Skirt with Sandals

When it comes to styling long pleated skirts with sandals, again you will look most modern if you go monotone. Go casual with a refined t-shirt or sweatshirt, and elevate it with a sweater in a luxe fabric like alpaca or cashmere.

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Keep the look loose, untucked, and breezy to fit with current times, and choose flat sandals in natural colors that complement the outfit and your skintone.

How to Style a Long Silk Skirt

Another popular skirt trend in the past couple of years is the long silk skirt. Often cut on the bias, this skirt, made of silk or another silky fabric, is also called a slip skirt and can hit anywhere from the calf to the floor.

The best way to modernize the slip skirt is in the same manner as the pleated skirt; go oversized, untucked, and if not monochromatic, all pieces in a similar color story (shades of red and pink, classic ivory or gray with black or brown, blush pink with tan, etc.).

Style a Long Silk Skirt with Boots

A juxtaposition of tough with the silk skirt feels modern and bold. Don't be afraid to pair your long silk skirt with moto boots, Chelsea boots, or lug-sole shoes.

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If you are not wearing a monochromatic ensemble, consider “bookending” your look by having your top match your boots. This will make boots, especially chunky ones, look purposeful.

Style a Long Silk Skirt with Sneakers

Again, the juxtaposition of the silky fabric and formal-ish skirt length and sneakers feels really modern in 2025.

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While my look is more elevated, you can also go casual with oversized t-shirts which is very on-trend this year.

Style a Long Silk Skirt with Sandals

A great way to take that midi or maxi length silky skirt into summer is with a pair of sandals. No need to be precious and keep it dressy, again a juxtaposition of shiny with matte, dressy with casual is quite stylish.

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Flat slide and strappy sandals are a great fit with your silk skirt; tie one of your button-front boyfriend style shirts over it and grab a straw tote for a look that is perennially chic.

How to Style a Long Leather Skirt

I often get asked how to style a long leather skirt. I think the top part of an outfit with a long leather skirt is pretty easy, and can be inspired by the looks above.

However, the shoes are where folks have trouble, especially with the changes in fashion trends. It used to be an almond- or pointed-toe leather pump with a slim heel was a safe bet, but in 2025 that can look dated (unless that's your signature style). My tips:

• Have your shoes match your skirt. If your skirt is smooth black leather, have smooth black leather boots or shoes. Unless you're an expert stylist, I'd hold off on mixing suede boots or glazed heels with a leather skirt.
• Rock the sneakers! Sneakers are so chic with leather skirts. With the heft of leather, you can pair your skirt with anything from the streamlined retro-inspired styles to more chunky of sneakers. Here, don't worry the textile of your sneaker; suede, leather, mesh, and nylon will all work.
• Have some heft. If it's a slim heel and thin sole, be sure it's a closed-toe shoe. If it's a more open shoe, have a more solid sole and/or heel. If it's a flat, it should be structured with a higher vamp (no ballet slippers).
• Play with hoisery. With a long leather skirt, you can have fun with patterned and lace stockings, trouser socks, crew socks, and pops of color and print. A lug-sole black loafer with socks would bring a modern touch to a classic longer leather skirt.

I hope these tips help you style long skirts in contemporary ways. Long skirts aren't going away any time soon, and they are easy to find when thrifting and shopping resale. With a switch of shoes and some updated styling tips, skirts you've owned for decades can look brand new!