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25 Ways To Style A Maxi Skirt For Effortless Cool Girl Looks

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If you have a maxi skirt but no idea how to style it without looking drab – you’re in luck! Here are 25 chic ways to wear a maxi skirt, no matter the occasion.

Maxi skirts are a staple in any everyday wardrobe. They come in many different colors, lengths, and styles that you can wear a longer-length maxi skirt to work, on the weekends with friends, or even at formal events in place of a dress!

This wardrobe staple was first introduced in the 1960s, and they have only continued to gain popularity as the years go by. When styled right, maxi skirts look flattering on any body shape.

However, if styling isn’t your forte, you’re in luck! We’ve explored 25 of the best ways to style a long maxi skirt so you can look stylish no matter the time of year.

The 25 Best Ways to Wear a Maxi Skirt

1. Knit Blouse


As we approach the fall months and cold weather, preparing your transitional wardrobe is key for dressing for the rapid weather change. A knit top is a great addition to your closet as it provides the warmth of a sweater without being too cozy.

If it’s still the tail end of summer, style this with sandals and an oversized hobo bag for a laidback look; otherwise, for the fall months, this is perfectly paired with chunky boots and a tote bag.

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MADEWELL Crochet Button-Up Sweater Top
MADEWELL

Crochet Button-Up Sweater Top

At Nordstrom

 Reformation Isabel Satin Skirt
Reformation

Isabel Satin Skirt

At Reformation

Totême T-lock grain leather top handle bag
Totême

T-lock Grain Leather Top Handle Bag

At Luisa Via Roma

2. Beige Button-Up


A button-down shirt is a great option for a formal wear look, especially in warmer weather. Paired with a loose, breezy maxi skirt, this is great if you are a corporate girlie and spend most of your summer days behind your desk.

This can be layered easily and are an extremely versatile piece of clothing. They’re also great to wear in the fall when it starts getting chilly outside, but you can still show off your summer tan by wearing them open with a tank underneath.

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& Other Stories Oversized Patch Pocket Shirt
& Other Stories

Oversized Patch Pocket Shirt

At & Other Stories

Misook Cable-Knit A-Line Maxi Skir
Misook

Cable-Knit A-Line Maxi Skirt

At Neiman Marcus

Hermès Box Calfskin Oran Sandals
Hermès

Box Calfskin Oran Sandals

At Fashionphile

3. White Tank Top


A simple white tank top is a staple piece of clothing. A plain tank top is perfect for wearing alone in the hot summer months and can be layered under other blouses and sweaters in the winter to provide an extra layer of warmth.

Form-fitting tank tops will contrast with the loose silhouette of your maxi skirt, and it makes for a chic option to wear with your skirt for the summer. For ultimate versatility, a great choice would be getting a plain tank top in a neutral color to pair with different types of skirts and outerwear.

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ALLSAINTS Rina Cropped Tank
ALLSAINTS

Rina Cropped Tank

At Revolve

Figue Poppy Eyelet Embroidered Maxi Skirt
Figue

Poppy Eyelet Embroidered Maxi Skirt

At Neiman Marcus

Lele Sadoughi Lily Claw Clip
Lele Sadoughi

Lily Claw Clip

At Revolve

4. White Crop Top


Cropped tops are a perfect choice to wear with high-waisted maxi skirts as the sliver of skin it exposes breaks up the silhouette keeping the look fresh and young!

A white top is also easily matched with any color and is a staple for a capsule wardrobe. To keep this look chic and sophisticated, pair this with neutral accessories.

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1.State Button Front Top
1.STATE

Button Front Top

At Revolve

Free People Simply Smitten Maxi Skirt
Free People

Simply Smitten Maxi Skirt

At Revolve

LOEWE Mini Gate Leather Convertible Bag
LOEWE

Mini Gate Leather Convertible Bag

At Nordstrom

5. Oversized Blazer


An oversized blazer is the perfect slouchy accompaniment to a silky slip maxi skirt. This pair references the comfortable and still chic, Scandinavian style, which is soaring in popularity on social media.

The rest of the outfit can be kept minimalistic and dainty to balance the structure of the blazer.

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SANDRO Paris Alicia Blazer
SANDRO Paris

Alicia Blazer

At Nordstrom

Significant Other Alice Skirt
Significant Other

Alice Skirt

At Revolve

Christian Dior Grained Calfskin Saddle Bag
Christian Dior

Grained Calfskin Saddle Bag White

At FashionPhile

6. White Long Sleeve Blouse


Depending on your personal style, and level of modesty, a long-sleeve blouse is a great look paired with a maxi skirt. If you’re on a beachside vacation where the weather can veer on being chilly, this is the perfect effortless outfit.

If modesty isn’t a consideration, but you like the idea of the long sleeves, go for a blouse with a plunging neckline or a low back/backless detail for a bit of drama.

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Reformation Livvy Top
Reformation

Livvy Top

At Reformation

Reformation Sadie Skirt
Reformation

Sadie Skirt

At Reformation

Clérgerie Paris Dylan Denim Peep-Toe Platform Pumps
Clérgerie Paris

Dylan Denim Platform Pumps

At Neiman Marcus

7. Colorful Tank Top


A tank top in a bold color is a great simple way to incorporate some color into your look for any season. Bright colors can be a scary territory to venture into if you’re not experienced with styling different colors to suit your skin tone.

However, because a tank means more of your skin will be on display than the tank, this doesn’t need to be a consideration.

If you’re already experimental with your fashion, why not wear a matching top and maxi skirt in different shades of the same color for a perfect summer look? So not to overpower the overall outfit, keep your hair and makeup minimal for that effortless Scandinavian aesthetic.

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& Other Stories Fitted Tank Top
& Other Stories

Fitted Tank Top

At & Other Stories

Jacquemus Novio linen maxi skirt
Jacquemus

Novio Linen Maxi Skirt

At Net-A-Porter

Veronica Beard Foley Leather Ankle-Wrap Thong Sandals
Veronica Beard

Foley Leather Ankle-Wrap Sandals

At Neiman Marcus

8. Oversized Waistcoat


Maxi skirts are inherently not extremely formal, so if you’re looking to style this for a formal or work event, pay close attention to the structure of your top. A waistcoat was traditionally part of a men’s three-piece suit, but with changing tastes in womenswear veering towards an androgynous style, this is now a staple piece.

An oversized waistcoat is the best of both worlds as it is structured to add some edge to the outfit, but the relaxed, oversized vibe plays off a flowy maxi skirt.

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Jil Sander Tailored Cotton Vest
JIL SANDER

Tailored Cotton Vest

At Neiman Marcus

Free People x Revolve Make You Mine Slip Skirt
Free People

x Revolve Make You Mine Slip Skirt

At Revolve

NEOUS Giena leather sandals
NEOUS

Giena Leather Sandals

At Net-A-Porter

9. Oversized Tee


Nothing beats an oversized graphic tee, even in a chic wardrobe. Some occasions call for a relaxed vibe that can’t be replicated from anything other than a classic ol’ tee.

This pairs perfectly with a slimming slip skirt, as an a-line maxi skirt could look frumpy paired with an oversized top. The rest of the outfit can be kept edgy with black dad sandals and sharp-edged sunnies.

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Black oversized The Row t-shirt
THE ROW

Gelsona Oversize Cotton T-Shirt

At Nordstrom

Auteur Mia Skirt
Auteur

Mia Skirt

At Revolve

Saint Laurent 53mm Cat Eye Sunglasses
Saint Laurent

Cat Eye Sunglasses

At Nordstrom

10. Sleeveless Knit Top


A sleeveless knit top somewhat contradicts itself, but it is perfect for the period between summer and fall. A maxi denim skirt has been popping up on the runways for the past few seasons and is a trend here to stay.

To keep this ‘cool girl’ look chic, keep the accessories minimal and elevated. Dad sandals are a summer staple and a great option for walking through the city streets.

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& Other Stories Sleeveless Mock Neck Ribbed Top
& Other Stories

Sleeveless Mock Neck Ribbed Top

At & Other Stories

Reformation Myles Maxi Skirt
Reformation

Myles Maxi Skirt

At Reformation

Prada Quilted Patent Slingback Sport Sandals
Prada

Quilted Patent Sport Sandals

At Neiman Marcus

11. Multicolor Shirt


A multicolor shirt is the perfect way to get a pop of color in your maxi skirt outfit without compromising on structure and elegance. For those looking to incorporate their personal style into their office outfits, this is a great styling idea.

If you’re willing to go even further, matching your accessories to the accent color of the shirt will tie together the overall outfit.

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Solid & Striped The Arlette Shirt
Solid & Striped

The Arlette Shirt

At Revolve

Jacquemus Novio linen maxi skirt
Jacquemus

Novio Linen Maxi Skirt

At Net-a-Porter

Miu Miu Wander matelassé nappa leather mini hobo bag
MIU MIU

Wander Matelassé Hobo Bag

At Miu Miu

12. Strappy Top


For a more casual look during the summer season, going for a cami top [similar to a tank top but with spaghetti straps] is a great way to beat the summer heat.

Cami tops come in all ranges of patterns and colors, so you can find one perfect for the occasion, though this is especially great for easy vacation dressing.

Pairing this with simple strappy sandals and a fun handbag will result in that model-off-duty ‘I woke up like this’ look.

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& Other Stories Strappy Floral-Trimmed Top
& Other Stories

Strappy Floral-Trimmed Top

At & Other Stories

 Lovers and Friends Zariah Skirt
Lovers and Friends

Zariah Skirt

At Revolve

Saint Laurent Leather YSL T-Strap Thong Sandals
Saint Laurent

Leather YSL T-Strap Thong Sandals

At Neiman Marcus

13. Classic White Tee


Nothing beats a classic white tee! These can be paired with just about anything and this includes a maxi skirt. This is a great option if you have a bright or multicolor maxi skirt that you want to sober down.

If you want to elevate this look, go for a pair of fun kitten heels to play into the Y2K micro-trend, as well as chunky minimal jewelry – perfect for a sundowner event.

recreate this look
Reformation Muse Tee
Reformation

Muse Tee

At Reformation

Reformation Tazz Maxi Denim Skirt
Reformation

Tazz Maxi Denim Skirt

At Reformation

Jimmy Choo Amita Glitter Slingback Ballerina Pumps
Jimmy Choo

Amita Glitter Slingback Pumps

At Neiman Marcus

14. Boyfriend shirt


For an edgier look, nothing really beats an oversized boyfriend shirt paired with a maxi skirt, particularly a slip skirt. As for the rest of your outfit, this is where a little more effort needs to be made, so this is a great option for all the shoe lovers out there.

Wear this maxi skirt look with high heels to keep it elevated and chic whilst still looking relaxed and effortless.

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Vitamin A Playa Oversized Shirt Dress
VITAMIN A

Playa Oversized Shirt Dress

At Revolve

Chloé Directional Rib Wool A-Line Skirt
Chloé

Directional Rib Wool A-Line Skirt

At Nordstrom

ATP Atelier Rosa cutout leather sandals
ATP Atelier

Rosa Cutout Leather Sandals

At Net-A-Porter

15. Denim Shirt


Denim is a great option for the cooler months, and what matches better with a denim maxi skirt than a denim shirt? Double denim was all the rage during the 2000s [remember Justin Timberlake on the red carpet?], and the resurgence of the Y2K trend means this is still a fashion-forward look.

This is still a great option with a non-denim skirt and can be worn open in place of a denim jacket during the transitional months.

To fully commit to the Y2K look, go for pointed-toe kitten heel booties and a shoulder bag in matching colors.

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KHAITE Argo denim shirt
KHAITE

Argo Denim Shirt

At Net-A-Porter

GRLFRND x Marianna Hewitt Amara Maxi Pencil Skirt with Back Slit
GRLFRND

x Marianna Hewitt Pencil Skirt

At Revolve

Balenciaga Le Cagole Lambskin Shoulder Bag
Balenciaga

Le Cagole Lambskin Shoulder Bag

At Nordstrom

16. Striped Shirt


A striped shirt is a classic and recurring recommendation from us at Chic Pursuit. Focusing on vertical lines or vertical stripes means the shirt will be flattering on your silhouette and, paired with a sleek maxi skirt, can be super elongating.

To keep this look casual, you can pair it with chunky dad sneakers or even dad sandals if you’re blessed with a hot sunny day.

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ANINE BING Mika Shirt
ANINE BING

Mika Shirt

At Revolve

Reformation Isabel Satin Skirt
Reformation

Isabel Satin Skirt

At Reformation

Bottega Veneta The Handle small intrecciato leather tote
Bottega Veneta

The Handle Intrecciato Leather Tote

At Net-A-Porter

17. Strapless Top


Nothing screams bohemian style like a maxi skirt and a strapless top. A tiered maxi skirt such as this is actually a traditional dress of the Romani gypsy group, and so is also known as a gypsy skirt. And so, to play off this flowy style, going for a strapless top that shows off your decolletage is a flattering look.

This can be worn with flat sandals in the summer or layered with a cropped cardigan or blazer for the chilly fall season.

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Amanda Uprichard X Revolve Mandy Rose Top
Amanda Uprichard

X Revolve Mandy Rose Top

At Revolve

Reformation Tazz Maxi Linen Skirt
Reformation

Tazz Maxi Linen Skirt

At Reformation

ANINE BING Black Mini Luna Bag
ANINE BING

Black Mini Luna Bag

At SSENSE

18. Bralette


For styling a maxi skirt for special occasions, going for an intricate or embellished bralette is the perfect juxtaposition. For all the petite ladies, this is a great option as the maxi skirt can drown your figure if not styled correctly, so having something ‘barely there’ on top will look fantastic.

If a bralette makes you feel too exposed, this can be layered with a classic white shirt and worn with flat sandals to avoid it looking tacky.

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Waimari Dinamita Top
Waimari

Dinamita Top

At Revolve

Reformation Lucy Skirt
Reformation

Lucy Skirt

At Reformation

Saint Laurent Tribute Suede Flat Slide Sandals
Saint Laurent

Tribute Suede Flat Slide Sandals

At Neiman Marcus

19. Vest


In the same way that waistcoats have surged in popularity, Scandinavian influencers have brought the vest back, and it’s here to stay. This is the perfect layering piece, as it can be worn alone or layered with a blouse or long-sleeve top.

To maintain the Scandinavian style, wear your maxi skirt outfit with a hobo bag and dad sandals in neutral tones.

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TWP Katherine Linen & Cotton Blend Vest
TWP

Katherine Linen & Cotton Blend Vest

At Neiman Marcus

Indah Daphne Maxi Skirt
Indah

Daphne Maxi Skirt

At Revolve

Birkenstock Arizona Genuine Shearling Lined Slide Sandals
Birkenstock

Arizona Genuine Shearling Sandals

At Nordstrom

20. Chambray Shirt


A great way to keep your maxi skirt looking formal and classic is with a chambray shirt. Chambray is a cotton-based fabric woven to look like denim, however, it has a lighter and airy texture, so it is perfect for the hot weather.

Because the chambray shirt has white undertones, this is best paired with a skirt in white or off-white. You can experiment with your accessories, however, one of the most popular shoe options this season are clogs.

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& Other Stories Oversized Patch Pocket Shirt
& Other Stories

Oversized Patch Pocket Shirt

At & Other Stories

PatBo Crochet Skirt
PatBo

Crochet Skirt

At Revolve

Larroudé Zuzi Bit Mules
Larroudé

Zuzi Bit Mules

At Nordstrom

21. Co-ord Set


If you’re not gifted with the natural ability of styling, a co-ord set is the perfect option for you. Maxi skirts and crop tops often come in matching sets owed to their ability to be dressed up for formal events and dressed down for easy vacation looks.

Because the outfit will likely pack a punch on its own, keep the rest of your accessories minimal.

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Reformation Elena Linen Two Piece
Reformation

Elena Linen Two Piece

At Reformation

RAYE Horizon Heel
RAYE

Horizon Heels

At Revolve

Prada Green Raffia Tote Bag
Prada

Green Raffia Tote Bag

At MyTheresa

22. Baby Tee


One of the best kinds of tops to wear with a maxi skirt is a baby tee. This is essentially a tight-fitting cropped t-shirt; like imagine if you wore one of your own childhood tees.

This was a super popular option for those invested in the Y2K trend, as this was usually paired with low-waisted jeans in favor of a bare mid-drift.

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RE/DONE x Hanes Cropped 60's Slim Tee
RE/DONE

x Hanes Cropped 60’s Slim Tee

At Revolve

Ralph Lauren Collection Emilien Silk Taffeta Skirt
Ralph Lauren Collection

Emilien Silk Taffeta Skirt

At Neiman Marcus

Amina Muaddi Rosie crystal-embellished suede slingback pumps
Amina Muaddi

Rosie Crystal-embellished Pumps

At Net-A-Porter

23. Bodysuit


A maxi skirt is not only the perfect transitional piece but also a great alternative for a beach cover-up paired with a swimsuit.

If you plan on wearing this on the beach or by the pool, it’s important to consider harmful UV rays and carry a sun hat.

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Tory Burch PRINTED ONE SHOULDER ONE-PIECE SWIMSUIT
Tory Burch

Printed One-Shoulder Swimsuit

At Tory Burch

Seafolly Palm Paradise Pareo
Seafolly

Palm Paradise Pareo

At Revolve

Kate Spade what the shell pearlized smooth leather seashell crossbody
Kate Spade

‘what the shell’ Crossbody

At Nordstrom

24. Blazer


For a more formal event where you need to look put together, a blazer is the perfect component. A slip skirt or a tulle maxi skirt is juxtaposed with a structured blazer and is the perfect balance of Masculin Féminin.

To elevate the look further, add a belt to cinch in the look and pair it with pointed pumps.

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Milly Avery Single-Button Cady Blazer
MILLY

Avery Single-Button Cady Blazer

At Neiman Marcus

Caroline Constas Cassiopeia Skirt
Caroline Constas

Cassiopeia Skirt

At Revolve

Valentino VLOGO Buckle Reversible Leather Belt
Valentino Garavani

VLOGO Buckle Reversible Belt

At Nordstrom

25. Cropped Tee


A cropped tee paired with a relaxed style of cotton maxi skirt is the perfect model-off-duty look. It’s great for a summer girls’ lunch as it can be dressed up or down.

As for the rest of your outfit, keep most of your accessories clean and minimal, but add some spice with statement sunglasses or a handbag to dress up the look.

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Lovers and Friends Coco Tee
Lovers and Friends

Coco Tee

At Revolve

Reformation Lucy Skirt
Reformation

Lucy Skirt

At Reformation

Bottega Veneta Half Moon Intrecciato Leather Pouch
Bottega Veneta

Half Moon Intrecciato Leather Pouch

At Nordstrom

We hope you got inspired by this guide on what to wear with a maxi skirt! If you’re still looking for more styling tips, check the posts down below.

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