Listen, I love a good mini skirt moment. Showing some leg can make me feel sexy and confident. But as I inch closer to 40, I find myself reaching for midi skirts more often. Midi skirts hit right below the knee, making them slightly more modest while still letting me feel cute and stylish.
I used to think midi skirts skewed matronly, but that couldn’t be further from the truth these days. From fitted bodycon midis to flowy, romantic A-line versions, midi skirts now come in endless silhouettes that flatter your figure. And they pair well with so many types of tops and shoes.
I turned to some of my favorite fashion influencers to scope out chic midi skirt outfit inspiration. From casual daytime looks to date night ensembles, I found 17 amazing ways to wear the midi. I especially love how many of these outfits incorporate seasonal trends like puff sleeves, pastels, and polka dots.
A versatile midi skirt has definitely earned a spot in my closet. Read on for ideas on how to wear midi skirts for all occasions!
And don’t forget to save your favorites to your Pinterest board by clicking the handy “pin it” button on each image!
1. Monochrome Magic
There’s something undeniably chic about an all-black outfit, and this outfit proves it. The flowing black midi skirt pairs beautifully with a loose-fitting white blouse, creating a contrast that’s both striking and sophisticated.
Slip on some black pointed-toe pumps and oversized black sunglasses, and you’re ready to take on the world in style.
2. Leather and Lace
For a look that’s equal parts edgy and feminine, try pairing a long black leather midi skirt (bonus points for a front slit!) with a simple black one-shoulder top. Black ankle boots complete the outfit, adding a touch of toughness to the overall vibe.
It’s the perfect choice for a night out with your girlfriends or a concert where you want to stand out from the crowd.
3. Tweed, Please
Preppy meets polished in this effortlessly chic ensemble. A gray tweed flared midi skirt is the star of the show, while a fitted black sweater provides a sleek contrast.
Black pointed-toe pumps and a classic black leather handbag tie the look together, making it ideal for the office or a more formal event where you want to look put-together and professional.
4. Tropical Breeze
Embrace the carefree spirit of summer with a colorful tropical print midi skirt. Keep the rest of the outfit simple with a crisp white button-down shirt and black slip-on sandals.
This breezy, boho-inspired look is perfect for a casual brunch with friends or a relaxed day of running errands in style.
5. Satin and Stripes
Who says you can’t mix textures and patterns? This outfit proves that sometimes, unexpected combinations yield the most stunning results. A black satin midi skirt serves as a luxe foundation, while a striped white button-down shirt adds a touch of visual interest.
Black slide sandals and a brown leather handbag complete the look, striking the perfect balance between sleek and laid-back.
6. Champagne Dreams
For a look that’s equal parts soft and sophisticated, reach for a silky champagne-colored midi skirt. Pair it with a cozy cream-colored knit sweater and black pointed-toe heels for a monochromatic effect that’s undeniably chic.
A black handbag and large hoop earrings add the perfect finishing touches, making this outfit ideal for a wedding or any other fancy fête on your calendar.
7. Green with Envy
Turn heads in the best way possible with this bold, bright ensemble. A vibrant green button-up blouse is the perfect partner for a black satin midi skirt, creating a color combination that’s sure to make a statement.
Neon green pointed-toe heels, oversized sunglasses, and a black studded clutch add to the eye-catching effect, while several well-chosen bracelets provide a touch of sparkle.
8. Lovely in Lace
Romance is in the air with this flirty, feminine outfit. A form-fitting black lace midi skirt is the epitome of elegance, while a lime green cropped tank top adds a pop of unexpected color.
Simple black sandals and a charming straw circle handbag complete the look, making it perfect for a summer date night or a garden party where you want to feel your most beautiful.
9. Pretty in Pink
Go bold or go home with this monochromatic masterpiece. A bright fuchsia midi skirt pairs perfectly with a matching cropped puff-sleeve blouse, creating a head-to-toe look that’s sure to turn heads.
Gold platform sandals add a touch of glamour and elongate your legs, while delicate gold earrings provide a subtle sparkle that catches the light just so.
This pretty in pink outfit is perfect for a variety of occasions, from a summer wedding to a rooftop cocktail party.
10. Denim Days
Casual, cool, and effortlessly chic, this outfit is perfect for those laid-back days when you still want to look put-together. A striped ribbed-knit long-sleeve top pairs perfectly with a dark wash denim midi skirt, while a thin brown leather belt adds a touch of polish.
Black ankle boots and dark oversized sunglasses complete the look, making it ideal for a day of running errands or grabbing coffee with friends.
11. Winter Whites
Who says you can’t wear white after Labor Day? This chic winter white ensemble proves that rules are meant to be broken.
A cropped white top pairs beautifully with a high-waisted white denim skirt featuring a front slit, creating a monochromatic look that’s both stylish and seasonally appropriate.
White Converse sneakers add a casual touch, while a fluffy beige jacket keeps you cozy on even the chilliest of days.
12. Spot On
Playful and polished, this outfit is perfect for the office or a lunch date with friends. A high-waisted polka dot midi skirt is the star of the show, while a long-sleeved black top provides a sleek contrast.
Black ankle boots complete the look, adding a touch of edge to an otherwise feminine ensemble. Don’t forget a small black crossbody bag to keep your essentials close at hand.
13. Walk on the Wild Side
Animal print is always a good idea, and this outfit proves it. A leopard print midi skirt takes center stage, while a black long-sleeved top provides a neutral backdrop.
Black high-top Converse sneakers add a touch of casual cool, making this outfit perfect for a concert or a night out with friends where you want to let your wild side shine.
14. Think Pink
Embrace your girly side with this pretty in pink ensemble. A bright pink high-waisted midi skirt with a bow detail is the epitome of femininity, while a white text print t-shirt adds a touch of whimsy.
Black ankle boots keep the look grounded, while dark sunglasses provide a touch of mystery. Wear this outfit to a day of shopping or a casual brunch with your besties.
15. Prepster Perfection
Channel your inner prep school star with this classic, collegiate-inspired look. A black high-waisted midi skirt with a thigh-high slit is the foundation, while a crisp white button-down shirt provides a polished contrast.
White crew socks and black loafers complete the ensemble, while a black backpack adds a touch of practicality. It’s the perfect outfit for a day on campus or a study session at your favorite coffee shop.
16. Denim Darling
Denim is always a good idea, and this outfit proves it. A midi denim skirt with a raw, frayed hem is the star of the show, while a casual white graphic t-shirt adds a touch of laid-back cool.
A chunky gold chain necklace, black sunglasses, and gold hoop earrings provide a touch of glam, while a structured black handbag and strappy nude heeled sandals complete the look.
Wear this outfit for a day of running errands or a casual lunch with friends.
17. Double Denim
Denim on denim, aka the Canadian tuxedo, is a trend that’s here to stay – and this outfit shows how to do it right. A light wash denim skirt with large pockets pairs perfectly with a denim shirt in the same light blue wash, creating a cohesive look that’s both stylish and comfortable.
A bright blue New York Yankees baseball cap adds a pop of color, while black sunglasses and pointed light blue heels provide a touch of glam.
A small mint green handbag completes the ensemble, making it perfect for a casual day out or a baseball game where you want to show your team spirit.
