Long skirt outfits: How to wear a maxi skirt this season according to a fashion editor

Looking for some long skirt outfits? Here's how to wear a maxi skirt using classic wardrobe staples

composite of three street style shots of long skirt outfits
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No matter the season or occasion, long skirt outfits fit the bill. A true wardrobe staple, knowing how to style a long skirt for any event will add infinite versatility to your closet.

Emerging with the 1970s 'hippy' clothing style, long and flowing maxi skirts quickly became a fashion favourite. Later revived by designer Richard Tyler as a huge '90s fashion trend, the look showed no signs of wavering even decades on. Most recently spotted on the runways of Miu Miu, Chanel, and Victoria Beckham, it is evident that long skirts will remain a huge spring/summer fashion trend for 2023, and are set to roll over into the autumn/winter fashion trends too. But whether you're a seasoned skirt wearer or you're ready to push your personal style further and experiment with new hemlines, curating long skirt oufits is surprisingly simple. 

“I love the versatility of a long skirt - they’re really easy to wear and make a great addition to every wardrobe,” says stylist and presenter Emma Lightbown. But when it comes to how to wear a maxi skirt, balancing proportions is key to achieving long skirt outfits that look chic and not frumpy. “Picking out the right shape top is important when wearing a maxi skirt. If it has a full, A-line or floaty silhouette stick to a more fitted top, while for a more curve-hugging pencil style, try styling it with something more structured on the top half such as a blazer.” Look no further for the best pieces to curate your own stylish long skirt outfits this season.

LONG SKIRT OUTFITS: Here's how to wear a maxi skirt according to a fashion editor

Long skirt outfits are great for pretty much any occasion, plus they go with a variety of different tops making getting dressed super easy. If you need some long skirt outfit ideas, here are seven ways to wear a maxi skirt, whatever the weather, to get you started. 

long skirt outfits with a sweater

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1. How to style a long skirt with a sweater

“When the weather starts to get a bit cooler you can’t beat a sweater and maxi skirt combo,” says Emma. Whether you team your best cashmere sweater with a more tailored skirt or a chunky knit with frothy tulle, it’s a great way to get more mileage out of a long skirt after the summer has gone. 

Many people think that maxi skirts are only for warmer months, as they're the obvious choice when exploring what is boho style, but a long skirt with a cozy knit is ideal as it gives extra coverage when the weather dips. Just avoid floor-sweeping styles, instead get skirts shortened to ankle length for practicality. For an alternative look, Emma recommends pairing your long skirt with a sweatshirt and trainers for a sports luxe-inspired look.  

Styling tip: “A French tuck - where you tuck in only the front of your top - will also elongate the body and emphasise your waist,” advises Emma.

long skirt outfits with t-shirts

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2. How to style a long skirt with a T-shirt

While you can’t get more classic than teaming a long skirt with your best white t-shirt, for an edgier look try a graphic print tee. A jersey or denim maxi teamed with a band t-shirt, chunky gold jewelry and heeled boots is the ultimate in dressed-down cool and the perfect choice for everything from a night out to a great brunch outfit idea. Alternatively, choose a full circle, or wide A-line skirt with more volume, a plain, fitted t-shirt and some canvas trainers for a nod to ‘50s casual aesthetic.

To render this look cold weather ready, try adding a fitted denim jacket, or use it to nail how to wear a denim shirt, in a slightly more oversized fit to finish the look. A denim shirt is an easy layering piece - it works with the casual feel of the t-shirt and behaves like a cardigan with added edge. 

Styling tip:  If you don't like tucking in your tee, choose a pencil or tube skirt fit to team with a longer-length t-shirt. This silhouette elongates your frame and as there's no volume in the skirt, it means you won't feel like you're losing your shape. You can also try a French-tuck or half-tuck with a looser fit t-shirt into the skirt waistband, so that you can reclaim your shape but still have a more relaxed feel. 

long skirt outfits with a blazer

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3. How to style a long skirt with a blazer

When it comes to how to wear a maxi skirt, the pairing of a full-length skirt with a blazer makes an obvious choice for the workplace, but don’t dismiss this long skirt outfit idea for a night out too. Choose a design in a luxurious fabric such as satin or silk to give it that evening sparkle, or as we head into party season, opt for a sequined maxi skirt to really bring the glamour. 

If you’re not sure how to style a blazer with a maxi skirt, the rule of 1/3 is a good one to adhere to. The idea here is that the skirt will take up 2/3 of the look, while the blazer will take up a 1/3 - ideally, it should end on your hips, otherwise, you risk looking swamped. 

Styling tip: Taller ladies can get away with comfortable flats, but if you’re on the petite side, get your best designer heels out!

long skirt outfits with a blouse

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4. How to style a long skirt with a blouse

A blouse and maxi skirt is the perfect Cottagecore outfit. What is cottagecore? We hear you cry. It’s a nostalgic fashion trend, which takes its inspiration from simpler times and is inspired by romanticised views of the English countryside. While often seen as a summer trend, this look can easily be taken into the fall season with some added layering. Swap bright bloom prints for block colours and dark florals, and layer big collar blouses under new season knits. 

When building a capsule wardrobe for women over 60, don't be afraid of incorporating current trends in a way that fits in with your personal style. However, if the uber-romantic Cottagecore look isn’t quite for you, a crisp white blouse tucked into a maxi pencil skirt is just one of the many long skirt outfit ideas to work into your wardrobe this season. The pencil or tubular maxi skirt offers a less frothy, more grungy finish.

Styling tip: If you’re petite, make sure your blouse is fitted and tucked into your skirt to avoid being swamped by the longer length. The taller you are, the more volume your shirt can take, try a high neck collar and a full sleeve style for an on-trend feel. 

long skirt outfits with knee high boots

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5. How to style a long skirt with boots

Chunky boots, or ones with a decent heel height, are some of the best winter boots to invest in and will ensure that your maxi skirt outfits don't end up dragging on the ground. After all, no-one wants a soggy hem. But for something on-trend and seasonless, there's no going wrong with cowboy boots. Plus, mastering how to wear cowboy boots is surprisingly simple, as they go with everything. 

Not sure how to wear knee high boots as part of your long skirt outfits? Choose a pair with a block heel for a boho, 70s take on the look that will work for transitional weather. If you want your maxi skirt outfit to be super chic, stick to a monochromatic palette.

Styling tip: Choosing a long skirt with a split or asymmetric hem will show off your boots more and really tie your whole look together.

long skirt outfits with trainers

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6. How to style a long skirt with trainers

Whether it's your best white trainers or nailing how to wear high top Converse, working trainers into your long skirt outfits creates a modern, stylish look. It doesn’t mean the rest of your ensemble has to be casual though - in fact, a chunky dad trainer can give a cool edge to a dressier maxi skirts. 

For a classic look that never dates, team your maxi skirt with a Breton top or white shirt, slip on your trainers and you’ll be ready for anything that the day throws at you. For a slouchy or casual long skirt outfit, take inspiration from how to style oversized t-shirts and go for a loose tee and slip skirt ensemble.

Styling tip: “Maxi skirts look fantastic with trainers, but getting the right length is crucial,” says Emma. “A skirt that finishes around the ankle is perfect for showing off your trainers.” 

long skirt outfits as a beach cover up

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7. How to style a long skirt as a beach cover-up

Thinking about some sun? If you're planning holiday outfit ideas but space is at a premium in your suitcase, putting together a few long skirt outfits is key to maximising your vacation wardrobe. Not only will it look chic in the bar come sundowner time, but a maxi skirt also works as one of the best beach-cover ups.

Emma recommends opting for something a bit floatier to make sure your long skirt outfit screams beach-ready. You could also try a hi-lo hemline or tiered maxi skirt for a more runway-inspired look when curating summer outfit ideas. Choose a design in a cheesecloth or chiffon fabric for super easy, non-creasing packing, that's also lovely and light in the heat.

Styling tip: Emma advises an elasticated waist for the ultimate in holiday comfort. “Stick to those with elasticated waists rather than buttons or a zip and choose colours that compliment your swimsuit,” she recommends.

Jayne Cherrington-Cook

With over 22 years’ experience in journalism, Jayne has written about a variety of subjects. She spent the start of her career within the world of film, interviewing Hollywood stars, attending premieres and lusting after red carpet outfits, and then moved into fashion, launching websites for big magazines such as Look, Woman’s Own and Wedding and working with top fashion brands such as Westfield, LK Bennett and Hunter. 

Career highlights include dressing up as Kylie (in gold hot pants!) for a national newspaper and working on big fashion events alongside Giles Deacon, Henry Holland and Naomi Campbell. 

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