7 Best Long Skirt Outfit Ideas, According to Celebrity Stylists originally appeared on Parade.
There’s nothing more whimsical and on trend than a long skirt, especially for those summer outfits where you want a cool breeze without showing too much leg. These denim or flowy pieces are fashionable, comfortable and can be styled in a number of ways depending on your preference and comfort level. Even celebrities like Taylor Swift and Kendall Jenner are frequently spotted in maxi skirts while out and about because they are flattering, trendy and can be dressed up or down depending on the occasion. Long skirt outfits are great for running errands, walking around the neighborhood or even wearing to the office if you have casual Fridays.
With that said, the best part about fashion is that there are no rules—you can wear whatever you want in any way as long as you feel confident and your best. Long skirts are one of many wardrobe pieces that you can opt for when you want to switch up your wardrobe and try something out of the norm.
Ahead, we spoke with celebrity stylists about everything related to long skirts from how to wear them for a more flattering finish to style ideas for when you’re putting together your next outfit and need some inspiration.
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How To Wear Long Skirts Without Looking Frumpy
The key to wearing long skirts without looking frumpy is all about proportion and intention. According to Stacy London, celebrity stylist for Kate Winslet and Liv Tyler and founder of “by Stacy London” sold exclusively at QVC, a common mistake is pairing too much volume on top with a long, flowy bottom, which can overwhelm the frame.
“Another way to avoid looking frumpy, is to tuck in your top, choose a cropped jacket, or define the waist to maintain shape,” London says. “Structure is everything so for all of my short girls, I recommend grabbing a midi skirt rather than a maxi to avoid trouble with length.”
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What Top Should You Wear With Long Skirts?
When it comes to figuring out the type of top to wear, London has some recommendations depending on the look you want to achieve.
“For a more refined look, a structured blouse or a slim fitting knit adds sophistication,” London says. “I style my clients in maxi skirts with a structured collar shirt for an elevated look (and for some pizazz, with accessories as well.) For something more relaxed, I opt for a soft, no nonsense tee or for a little bit more fun, a graphic tee.”
Pro tip: Tucking, tying or choosing a cropped length helps define the shape and keeps the proportions right when wearing a long skirt.
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How To Wear a Maxi Skirt Over 40
The best way to wear a maxi skirt over 40 is to simply just that—wear it. London is a firm believer of never being afraid to try out a new style or jumping into a new trend and that includes maxi skirts.
“Maxi skirts may not be for everyone but given their shape by nature they make the perfect base to tailor them to fit your sense of style,” she says. “It’s all about confidence, tailoring and knowing how to elevate the look. Pair it with pieces that feel current, intentional and uniquely you.”
For example, a crisp blouse, a sleek knit or a well-fitted blazer can bring polish and keep the outfit feeling modern. Plus, you’ll want to remember to define the waist whether through tucking, belting or choosing a high-rise cut, according to London.
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7 Best Long Skirt Outfit Ideas, According to Celebrity Stylists
1. Pair With a Classic White Button Down
A crisp white button-down is a staple as it’s clean, classic and polished, and it pairs well with long skirts for almost any occasion..
“When you throw it on with a black leather skirt, you create tension between soft and structured,” London says. “The shirt’s looseness gives you movement and ease, but then the skirt comes in, cinches everything, and gives you shape.”
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2. Denim on Denim
Denim-on-denim continues to be a strong trend because of its versatility and timeless appeal. “An oversized denim jacket paired with a denim maxi skirt creates a look that feels both relaxed and intentional,” London explains. “When styled thoughtfully, the combination feels elevated rather than dated. It’s a posh take on a Canadian tuxedo.”
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3. Wear With a Casual T-Shirt
London recommends pairing a long formal skirt with a casual t-shirt to create an intentional contrast that adds energy to the overall look. “The mix of elevated and everyday pieces makes the outfit feel modern and dynamic,” she says. “A tucked-in tee and defined waist help maintain structure, ensuring the silhouette remains flattering despite the relaxed top.”
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4. Rock a Bold Blazer
When it comes to long skirts, you can’t go wrong by pairing it with a blazer. “[A] blazer paired with [a] long denim skirt plays on formal and casual wear masterfully,” London says.
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5. Belt It
Desiree Miranda, a New York City and Miami-based celebrity stylist with clients like Natasha Parker and Bruna Petrillo, recommends styling a long skirt with a waist belt to accentuate the final look. “If you have a patterned maxi skirt with a bit more volume try tucking in a simple top and adding a waist belt to tie your look together,” she says.
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6. Get a Matching Set
Matching maxi skirt sets are a super easy and stylish way to wear the long skirt trend. “This one is great since the skirt has a bit more volume and you want to go with minimal fabric on top,” Miranda explains. “Showing a bit of the midriff can help elongate you and not cut you off in an unflattering way.”
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7. Style It With a Fitted Top
In some instances, a fitted top will work extremely well with a long skirt like in this instance on Nieves Alvarez. “Since the skirt has a bit of a pleated illusion you can get away with wearing something more fitted on top versus blousing a top out of the skirt,” Miranda says. “This is also a slimmer cut so it is wise to opt for a higher neck top option to balance out the proportions.”
Up Next:
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Sources:
Stacy London, celebrity stylist and founder of by Stacy London sold exclusively at QVC
Desiree Miranda, a New York City and Miami-based celebrity stylist
7 Best Long Skirt Outfit Ideas, According to Celebrity Stylists first appeared on Parade on Jul 11, 2025
This story was originally reported by Parade on Jul 11, 2025, where it first appeared.
