How to Style Maxi Skirts: 7 Stylist-Approved Long Skirt Outfits

Micro-mini this, itsy-bitsy that—there's been quite the buzz about mini skirts in recent seasons. But if you've grown fatigued by the flirty, thigh-grazing silhouette and all the discourse it's inspired (is Miu Miu's mini actually wearable?), turn your attention instead to the more mature sister of the skirt family: the maxi. The best maxi skirts offer astounding versatility, taking you from the beach to the office to your local neighborhood haunt for cocktail hour. And as Stitch Fix expert stylist Gillian McHattie explains, it comes down to which option you choose, of course, but also how you style a maxi skirt.

"There are endless patterns, silhouettes, and styles to choose from," she says of the maxi skirt gamut. It can be your new workwear staple: "For clients looking for an effortless and chic work outfit, a maxi skirt is top of my list because the length is appropriate for the office." But the floor-sweeping number also works as a casual piece to wear on the weekends, says McHattie. "I'm loving the resurgence of laidback, 70s-inspired maxi skirts, especially with the new release of the Daisy Jones & The Six series," the stylist offers, shouting out vintage-feeling "crocheted or embroidered patterns, flowy florals, faux fur, and brown leather" for spring 2023.

In short, there's a slew of maxi skirt options for women in 2023, guaranteeing you'll find one that perfectly matches your preference. Ahead, seven maxi skirt outfits and an edit of shop-ready pieces to get you situated for spring.

How to Style Maxi Skirts

Denim Maxi Skirt

"Denim maxi skirts are one of my favorite looks this season," McHattie shares. "For more adventurous clients, I recommend going all out and opting for a denim-on-denim look by styling a long jean skirt with a denim top and adding a pop of color with a suede bootie to really emphasize the maximalist western look."

Levi's Iconic Long Skirt with Belt

Mavi Jeans Tamara Oversize Cotton Denim Shirt

PEDRO Black Suede Leather Ankle Boots

Isabel Marant 49MM Round Sunglasses

Long Slip Skirt

"Right now, I’m loving a maxi slip skirt look paired with tall boots (like these from Dolce Vita) and an oversized sweater," shares McHattie. "This look is a perfect example of the Stich Fix-forecasted trend Proportion Play. What I love most about this look is that it’s extremely versatile because it incorporates staple closet pieces."

Banana Republic Dreamer Silk Maxi Skirt

Topshop Oversize Wrap Front Cardigan

Dolce Vita Eliot Suede Boot

Loewe Flamenco Mini Clutch

Floral Maxi Skirt

"With spring just around the corner, I recommend trying out the garden state trend," says McHattie, inviting you to lean into spring 2023's inspired and fresh-feeling take on florals. "Opt for a subtle flower-patterned maxi skirt to pair with a simple white top and your best ballet flats," offers the stylist.

Cara Cara Nathali Floral Tiered Maxi Skirt

STAUD Cotton Blend Felicity Top

Sam Edelman Felicia Ballet Flat

Ada Handmade Leather Wrap Belt

Long Leather Skirt

Unsurprisingly, leather will be a prevalent textile this spring, as the material is timeless and always manages to insert itself into the trend cycle no matter the season. However, the Stitch Fix stylist observes that she's "seeing a lot of warm neutrals such as browns and beiges" as opposed to the ever-standard black. "This brown leather maxi skirt from A.L.C is one of my favorite items at the moment because it's so chic and pairs well with both boots or flats," McHattie offers.

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A.L.C. Tracy Skirt

Anne Klein Sleeveless Rib Turtleneck Sweater

Vince Camuto Caseyl Knee High Boot

Coach Cary Leather Crossbody Bag

Pleated Maxi Skirt

Given that preppy style is experiencing a rebrand in 2023 (evolving from stuffy and conservative to more playful and subversive), the pleated skirt is in the middle of a fashion moment. Cash in on the momentum by opting for a long skirt done in pressed creases, like Manning Cartell's voluminous option. Then, team it with a simple and understated white tank top and an effortless pair of slip-on shoes. "For complimenting a longer hemline look, 91 percent of our stylists predict that low heels will dominate women’s shoes in 2023," McHattie shares, dubbing a maxi skirt paired with kitten heels a trending combination. 

Manning Cartell Kinetic Abstractions Maxi Skirt

Madewell Brightside Tank Top

BY FAR Evelyn Metallic Pointed Toe Mule

JENNY BIRD Izabella Collar

Black Maxi Skirt

"Stitch Fix predicted this year shoppers would focus on creating an Intentional Wardrobe, a personalized capsule closet with investment pieces that lend themselves to 24/7 dressing (i.e., the ability to wear a staple item for a variety of occasions and seasons)," describes McHattie. And a key item she sees shoppers gravitating toward is a neutral black maxi skirt. "I love a simple wrap skirt, such as this timeless black piece from B.Freedom, which can be seamlessly styled for the office or a weekend night out."

B. FREEDOM Simona Wrap Skirt

Lauren Ralph Lauren Leather Bomber Jacket

Good American Stretch-Jersey Thong Bodysuit

Vagabond Shoemakers Hedda Bootie

Crochet Maxi Skirt

McHattie encourages you to lean into a retro feel with your long skirt outfit, starting with a floor-sweeping option made of crochet. "For clients that want to take the '70s look a step further, try emulating the rock n’ roll vibe with a crocheted maxi skirt—like the below one from Theory—and pair it with distressed cowboy boots and a shimmery shacket."

Theory Tissage Open Stitch Maxi Skirt

Steve Madden Andee Sequin Check Shacket

Isabel Marant Dicker Suede Ankle Boots

Lu Goldie Milou Sunglasses

Meet the Expert

As a Stitch Fix Styling Team Lead, Gillian McHattie brings her fashion-forward expertise, a passion for personalized style, and over 8 years of industry experience to the role. Since joining the organization in November 2020, Gillian has managed and developed 50+ stylists across the Central Region and created informational and engaging content to create community, collaboration, and culture on Stitch Fix styling teams. She also serves as one of Stitch Fix’s brand ambassadors in press interviews, and delivers personalized style takeaways to readers in online editorial coverage.

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