23 Cute Skirt Outfits + How To Style Any Skirt

Up your wardrobe game with these cute skirt outfits!  These refreshing & adorable skirt outfits are a great twist to jeans and are absolutely irresistible! 

Whether you’re looking to spice up your work, school or date night look, these cute skirt outfits will do just the trick. You will find cute styles ranging from classy, trendy to even romantic silhouettes. Let these cute & irresistible outfits inspire your next shopping spree! 

How do you look cute in a skirt?

I recently got this question, which can be a little open ended. However there are a few stylish tips and tricks you can easily incorporate to look super cute in a skirt. 

  1. Choose a cute skirt to build your outfit around
  2. Next you will want to select a top that will complement your outfit. If it's chilly go for a sweater or long sleeve, and if warm out choose something nice and cool. You just want to make sure that your overall look feels balanced and lovely. 
  3. A fitted top pairs wonderfully with a loose or billowy skirt, while a tight or pencil style skirt can pair well with a loose fit blouse. You can tuck in your shirt if feels right to add extra dimention and shape to your look. 
  4. Complete your look with the right shoes. Go for sanalds in the warm months and booties or loafers are a great choice in the cooler months. If you are going to a special event or a sit down dinner, heels are also a fun choice to dress up your look. 

Are Skirts Casual?

Depending on the style of the skirt, it can be both casual or dressy. The way you style the skirt can also make it casual or dressy. So yes, skirts can be worn casually. 

You can dress a skirt with a cute tee and sandals for a casual look. To dress up the same skirt, wear it with a blouse and high heels for a cute dressed up look. 

Same skirt 2 ways: Dressy Vs. Casual


cute skirt outfits


What to wear with a skirt?

What to wear with a skirt depends on the type of skirt you will be styling and the event you will be attending. You can make a wild variety of cute outfits with a skirt. The possibilities are endless. 

There are also different types of skirts such as cuts and lengths to consider when styling a skirt. You can wear your skirt with a variety of tops, accessories and shoes to complete a cute skirt outfit. 

  1. Mini Skirt: Style a mini skirt with a bodysuit, cropped jacket and booties or sandals. 

  2. Midi Skirt: Wear your midi skirt with a blouse or sweater. Complete the look with flats or sneakers. 

  3. Maxi Skirt: Style your maxi skirt with a loose blouse or fitted top. Complete your look with a kimono and sandals

  4. Pencil Skirt: Style a pencil skirt with a blazer and loafers for a professional look. 

  5. Skater Skirt: Wear a skater skirt with a tucked in top or bodysuit, a cropped jacket and booties or sneakers. 

Let's Dive In!

cute skirt outfit

Shop Skirt  Top

Cute Aesthetic Skirt Outfit

This outfit is giving me all of the gossip girl vibes. Just like the leaves fall, I am also falling for the Late To Class Plaid Mini Skort! A woven tartan plaid shapes a high waist with an asymmetrical button up front, side seam zipper, and built in shorts. We're absolutely obsessed with this 90's inspired skort. Pair with tights, your favorite boots, and a cozy sweater for the cutest fall look!

cute skirt outfits


Shop Skirt Top

 Cute Skirt And Shirt Outfit

Feel fresh and flirty in the Sweet Blossom Skirt. This two tiered skirt features a tiny, beautiful floral print and an elastic waist band. Pair this with a pretty pink blouse for a great special occasion outfit.

cute skirt outfits

Shop Skirt  Sweater 

Cute Skirt and Sweater Outfit

Layer your midi skirt with a soft sweater for a delightful winter or early spring look. This lacey layered skirt will help you feel feminine and so chic! It features a stretchy, elastic waist. It's also lined, lightweight and flowy. This skirt looks so cute dressed up with a beautiful blouse or dressed down with a tee shirt and denim jacket.

cute skirt outfits


Shop Skirt  Blazer 

Cute skirt outfit for work

Try layering your skirt with a bodysuit top and blazer for that chic workwear look. You'll look professional with a fun and refreshing twist. 

cute skirt outfits

Shop Skirt, Top, Jacket

Cute Skirt Outfit For Spring

It is so easy to love the Two Hearts Meet Maxi Skirt! A stunning linen/cotton blend shapes this maxi. Perfected with an elasticated waistband and side pockets, the flowy fit ends at ankle length, slightly flaring out to create an a-line silhouette.


cute skirt outfits

Shop Skirt , Top

Cute Aesthetic Skirt Outfits Set

I love a cute skirt set to set the tone for a fun afternoon. This look is so aesthetically pleasing and sweet. When you want to look your best, leave it up to the Golden Hour Skirt to get you there! This adorable midi length skirt features a tiered ruffle design, a-line silhouette, and white floral print that decorates the entire skirt! Pair this with white heels, and a simple blouse and stand out! 


Shop  Top

Cute Skirt Outfit For Summer

I absolutely adore this set for a sunny summers day! I worn mine to the lavender festival and got so many compliments on it that day. The nice thing is that its lightweight, cute and cool. It's perfect for a morning at the farmers market, the beach or a picnic. It's also a great idea to pack for your next vacation. Whatever fun things you will be doing, this cute skirt set will take you there. 

cute skirt outfits

Shop Skirt, Bag

Cute Skirt and Top Outfits

Throw on the Easy Breezy Skirt and instantly look put together! Dainty Blue and white flowers sweep across the entire skirt, in a tiered maxi silhouette with an elastic waistband. You'll be feeling comfortable and stylish in a breeze! Pair with your favorite sandals and tank for an adorable spring look! 


cute skirt outfits

Shop Skirt, Sweater 

Jean Skirt Outfit 

Go for a casual and preppy look with a jean skort. Denim skirts are great because you are simply swapping out your blue shorts for a skirt. Dress up your look in a comfortable way with the Jalissa High Waist Overlap Denim Skort! Stretchy, dark wash denim shapes a hi-rise waist with zipper fly and two back pockets. An overlapping panel wraps atop the front side finished with a double button closure with an assymetrical hem and front pocket. 

cute skirt outfits

Shop Skirt, Jacket 

Cute Skirt & Jean Jacket Outfit

Be the center of attention in the Estrella Patterned Skirt! This stunning skirt features an ultra soft faux suede, embroidered in a geometric black design overlaying the front. Complete with a back zipper closure and inner lining for functionality and comfort!


cute skirt outfits

Shop Skirt, Tops

Countrycore Skirt Outfit 

The perfect maxi for a mid-summers day! Its comfy, casual and cute. If you're looking for a way to be on trend and stay cool in the summer then the All In Favor Maxi Skirt is the perfect pick for you! As soon as you discover the flowy, maxi length combined with the elasticated waistband, and zig-zag tiered design you'll fall in love! Keep it boho with your favorite strappy sandals, a lace bralette, and your favorite matching kimono!

cute skirt outfits

Shop Skirt

Cute Boho Skirt Outfit Idea

We are in awe of this stunning skirt and it's because of the beautiful details! The Make Me Feel Good Skirt features a smocked waistband that tops three tiers with a tiny ruffle at the seams. Each tier features a different floral design that works cohesively together. Pair this item with your favorite boots!


cute skirt outfits

Shop Skirt, Top

Cute skirt Outfit For Winter 

Maximize a maxi skirt by wearing it year round. Choose a maxi length skirt in winter to stay cozy and layer with leggings or tights underneath for even more coverage. The Roam The World Skirt is a tiered skirt with beautiful movement. This skirt is made of a stretch fabric with a comfortable waistband! Pair it with a lightweight sweater and ankle boots for a fun boho look.

cute skirt outfits

Shop Skirt, Top, Shoes 

Cute skirt outfit for work

Cute for the office or a night out! Go for a blouse and blazer for work or swap this skirt with a sequin top and heels for a night out. The Just A Girl Side Slit Skirt in Black is the perfect addition to your wardrobe. With its thick banded hi-waist, slim fit, and stretchy, non-sheer fabric, you'll feel comfortable and stylish all day long. The side slits and knee length hem add a touch of fun, while the buttery soft fabric will keep you cozy. Dress it up or keep it casual, this skirt is just what you need!


cute skirt outfits

Shop Skirt, Blouse

Cute Skirt Outfit With Booties 

I love this preppy chic look for spring and summer! Especially paired with the white boots! A Perfect look for a day on the go. The New Age City Girl Skirt is here to prove that wardrobe essentials don't have to be boring! This cute fall staple can be styled so many different ways, you'll never get tired of it. Featuring a stretchy brushed knit that shapes a a mini a-line silhouette, with a ribbed hem and elastic waistband. For the perfect touch of fall this adorable mini is painted in a brown and pink plaid print. Pair with a cropped jacket and knee high boots for a look that will turn heads!


cute skirt outfits

Shop Skirts, Blouse

Date Night Mini Skirt Outfit

Go for a vegan leather skirt for a fun and flirty date night look. Pair a mini skirt with a long sleeve blouse to keep your look in balance. Kitten heels and a mini crossover bag complete a look perfect for your next night out. 

Cute skirt outfits

Shop Skirt, Kimono 

Casual Boho Skirt Outfit 

Pair the Get Away Maxi Skirt with a boho top and sandals for an easy, put together look! This flowy, lightweight skirt has all the potential to become a new go-to with a comfortable elastic waistband, maxi length silhouette, side slits at both side seams and a subtle shine to the fabric.


cute skirt outfit


Shop Skirt

Clueless Inspired Skirt Outfit 

The 90's are calling...they want their skirt back! The best thing about fashion is that trends are constantly cycling and we are so glad the plaid mini has returned! The Call Me On Line Two Plaid Mini Skort has the cutest details, featuring a black and white plaid print that decorates the entire skirt, topping an elasticated high waist, hidden shorts, and a ruffle hem. Go total 90's with knee high socks and a white button up or keep it modern with a black sweater and heeled boots. 


cute skirt outfits


Shop Skirt

Comfy Skirt Outfit Idea 

A comfy and cute skirt is perfect for anyday! Made in an incredibly soft fabric, the Falling For You Skirt In Heather Gray is an elegant statement piece. It's designed to sit at the waist with flattering pleats and a floor length hem. It features an elastic waist that is covered by a darling bow. Pair it with a light summery top and strappy sandals for the ultimate summer look.


cute skirt outfit


Shop Skirt, Jacket

Winter Skirt Outfit with Boots 

Dress to impress in the the Cathedral Printed Skirt. This beautiful classic mid length skirt speaks to your sense of style with its stunning blue/bronze motif pattern the perfect chiffon pleats to elevate you outfit. Pairing effortlessly with so many tops and shoes in your wardrobe, you can dress up for a professional polished look or style with trainers or clogs for a leisure day. 


cute skirt outfits


Shop Skirt, Jacket 

Animal Print Skirt Outfit

Walk on the wild side in the Carefree Animal Print Skirt. The curved hemline, elastic waist and midi length are the perfect recipe for elegance! Pair with black heels, a black top, and a matching bag for a sleek, put-together fit! 


cute skirt outfits


Shop Skirt, Tank

Casual Skirt Outfit

The Golden Blooms Skirt is two tiers of floral perfection! This short skirt has an elastic waistband and is made of comfortable fabric. Try wearing it with a bodysuit and gold jewelry for a flawless outfit.


There are so many unique and fun ways to style a cute skirt outfit. Just remember to have fun and play around with your look until you like what you see. I hope that these outfits gave you some cute skirt outfits ideas! 

Just remember that the most important thing is to feel great in what you are wearing. If you have any questions on how to style a skirt be sure to let me know in the comments below! 😍

Every Tuesday I release a new collection of cute new outfits and create lots of fun new looks for style inspo 💕

Check out my complete collection of cute styles HERE

cute skirt outfits



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