As a style coach and a toddler mom, I am grateful that longer-length skirts and dresses are here to stay! We have seen hemlines inching back up (lots of miniskirts on the Spring 2022 runway), but designers got the memo that longer lengths are nice and breezy for the summer weather and oh-so-practical for our busy lives.

If you’ve taken the plunge and purchased a midi skirt, or you’ve been pondering snagging one but felt uncertain how to style this silhouette, then you are in the right place. I love helping my style coaching clients feel confident in their outfit-making, and I am here to be your personal guide on the art of styling a midi skirt!

Whether you are tall, petite, or of average height, there is a flattering midi skirt out there for you. My clients are of all body types and sizes, and I’ve found it really comes down to the fabric’s drape and the skirt’s length. For example, my petite clients tend to do best in petite-sized skirts (brands like Ann Taylor, Nic+Zoe, LOFT), or at least those that hit right above the calf muscle.

Woman modeling striped tie waist Ann Taylor skirtPin
Striped tie-waist skirt, on sale for $119.99 (reg. $139), at Ann Taylor | Image: Ann Taylor

My curvier clients need fabrics that drape well versus stiff, starched cotton or anything too bulky. We want the midi skirt to lay beautifully over their curves.

Woman modeling a mosaic wrap skirt from LOFTPin
Mosaic midi-wrap skirt, on sale for $69.99 (reg. $79.50), at LOFT | Image: LOFT

Once you’ve found the right midi skirt for your body type, you can work on styling it in multiple ways.

Shopping Tip: Before you purchase something, really consider how you will wear it. Be sure you can envision at least two ways to wear it to confirm that it’s a versatile piece that deserves a place in your closet.

TIP #1: Pair your midi skirt with an “up-leveled” top.

The FIRST way to style a midi skirt is simple, easy, and great for a casual day; it requires having “up-leveled” tops in your closet. What makes a shirt up-leveled is interesting details that help your outfit feel more pulled together, such as a ruffle, a tie waist, or an eyelet trim.

If you have these fun basics on hand, you can throw them on with your midi skirt for an easy outfit combination. When wearing a midi skirt, it’s important to fully tuck in your top for the most flattering look. Or, if you don’t like to tuck in your tops, opt for one that ties at the waist for a polished look.

Complete your casual look with a pair of white sneakers, slide sandals, or even a gladiator sandal (if you are on the taller side).

For a fun visual of how I styled my own midi skirt with an up-leveled tee, check out my video here.

Woman modeling pineapple linen blend button Ann Taylor skirtPin
Pineapple linen-blend button maxi skirt, on sale for $129.99 (reg. $149), at Ann Taylor | Image: Ann Taylor
Woman modeling a red floral midi skirt from RailsPin
Rosetta red ditsy floral skirt, $178, at Rails | Image: Rails
Woman wearing sleeveless tie-front top from Karen Kane with leopard-print skirtPin
Sleeveless tie-front top, on sale for $29.75 (reg. $119), at Karen Kane | Image: Karen Kane

TIP #2: Pair your midi skirt with a silk blouse.

The SECOND way to style a midi skirt is best for a fun dinner out, a party, or even work. Pair the skirt with a silk blouse (or any fabric with a good drape, so it doesn’t add bulk, as the skirt is already full).

If it’s a long sleeve blouse, try rolling up the sleeves to three-quarter length for the most flattering look. And as always, fully tuck the shirt into your skirt. You can complete the outfit with a belt at the natural waist for a more polished and current look. Depending on where you are going, your shoes will follow suit — a close-toe block heel pump is excellent for work, and a pretty sandal or espadrille is perfect for an evening out.

Woman wearing a tiered maxi skirt from EloquiiPin
Tiered maxi skirt, $89.95, at Eloquii | Image: Eloquii
Woman wearing a black REISS Drew contrast pleated midi skirt from Bloomingdale'sPin
REISS Drew contrast pleated midi skirt, on sale for $112 (reg. $265), at Bloomingdale’s | Image: Bloomingdale’s
Woman wearing at palm leaf-print cotton voile skirt from Ralph LaurenPin
Palm leaf-print cotton voile skirt, $145, at Ralph Lauren | Image: Ralph Lauren

TIP #3: Pair your midi skirt with a jacket.

The THIRD way to style a midi skirt is perfect for transitional weather as it involves a classic denim jacket. There’s nothing more effortlessly pulled together than a great tee with a denim jacket and midi skirt, but selecting the right denim jacket for this look is essential. It requires a more cropped, tailored denim jacket, and one with stretch is important for comfort and fit. Like with the long sleeve silk blouse, try rolling up the sleeves for a more flattering look.

As for the type of tee to put under the denim jacket, it all depends on your personal style. Many women love a graphic tee (words, images, music, etc.) paired with the skirt and jacket. Others enjoy a more classic look and opt for a v-neck tee in a solid color, like white. No matter the tee, always fully tuck it into the skirt for the most flattering look.

Opt for a pair of sleek sneakers, slide sandals, or even an espadrille wedge to finish the outfit! It all depends on your style and where your day will be taking you.

Woman wearing a blossom midi wrap skirt from LOFT with a denim jacketPin
Blossom midi wrap skirt, on sale for $64.99 (reg. $79.50) at LOFT | Image: LOFT
Woman wearing a retro floral full skirt from Shopbop with a denim jacketPin
Retro floral full skirt, on sale for $103.60 (reg. $148), at Shopbop | Image: Shopbop

Now it’s time to implement your new midi skirt tips! If you already have a midi skirt, look in your closet and see if you have these tops, a denim jacket, and the shoes to complete your skirt ensembles. Missing the midi skirt? Time to take my tips and find the right midi skirt for your silhouette and style.

Megan LaRussa is a personal fashion stylist and style expert specializing in helping women look and feel their best through their wardrobes. For more style tips and inspiration, visit Megan’s website, follow her on Facebook and Instagram, or sign up for her complimentary weekly newsletter here.

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Author: Megan LaRussa Chenoweth
About the Author
Megan LaRussa Chenoweth

Megan LaRussa Chenoweth of Style Yourself Chic is a Style Coach that loves nothing more than guiding her clients & community to look and feel their best everyday.