How to Style Midi Skirt: 5 Ways

Monday, March 13, 2023
How to Style Midi Skirt: 5 Ways

You’ve seen it around these parts before—that not-too-long, not-too-short wonder of a skirt, the true Goldilocks of garments. Yes, we’re talking about the midi skirt. Their calf-brushing lengths instantly add depth and intrigue to any look, and their many styles—pleated, A-line, or straight with a slit, to name a few—lead to endless styling possibilities.

If this skirt style is a new addition to your wardrobe, however, you may still be wondering how to wear one. Fear not—we have all the style ideas to get you started.

The midi length skirt appears in a variety of cuts, fabrics, and fits, and has a home in everyone’s wardrobe. Dressed up or down, for the café or for the runway, the midi skirt can be a style you step into for any occasion. If you’re looking for inspiration for how to style a skirt as iconic as it is fashionable, look no further than these six styling ideas. 

#1 With a Knit Sweater

Originally a reaction against the proliferation of the mini skirt, the midi skirt brought low hemlines back into fashion magazines and onto the streets. Once known by its French name, the longuette, the midi skirt encapsulated Paris’s wartime aesthetic of “gritty glamour.” When looking for midi skirt outfit ideas, then, one of the best places to start is with that aesthetic as inspiration.

Especially suitable if you’re newly slipping into the midi world, pairing a midi skirt with a cozy sweater is a go-to styling choice. With so much sweater variety out there, this look can go more than a few different ways, but rest assured that this combination is a fail-proof way to capture that “gritty glamour” style. Here are some different sweater-skirt combos we love:

  • Satin midi skirt with a chunky knit – This look screams chic with a capital "C," all because of another "C": contrast. When paired with a chunky, texture-forward sweater, the silky smooth, no-frills drape of a satin midi skirt makes for an alluring contrast—not to mention divine comfort.


  • Flowy midi skirt with a fitted knit – One of the traits that have cemented the midi as an iconic garment is its movement and flow, two traits that were limited in its short-hemmed sibling, the mini skirt. Let your midi skirt’s movement shine, and highlight its flow with a more fitted knit sweater on top for a balanced, feminine outfit with a Hepburn-esque touch.


  • Midi skirt with a cardigan – The midi skirt can pair perfectly with a number of knit layers, both buttoned-up and oversized. Whether you go for a smartly cropped cardi or a long, boho-inspired cardigan, your midi skirt outfit will surely be taken up a level. An extra tip: wear a high-waisted midi skirt to accentuate your waist and enhance your proportions, or try a French tuck with an oversized sweater to highlight your frame.

Whether it’s with heeled sandals or combat boots, no matter how you mix and match your midi, know that you’re building a cohesive style perfect for summer to fall transition outfits. Any other midi styles in this guide could also be made into a versatile year-round look; just throw on a sweater as the evening chill rolls in and give a whole new look to your midi skirt outfit.


woman wearing light blue blouse and printed midi skirt

#2 With a Buttoned Blouse

White sneakers, a black graphic tee, and a good pair of denim jeans—many of us fall back on our staples in a pinch, but one wardrobe staple that can elevate any midi skirt look is a button-up blouse. If you’ve been wondering how to style a blouse that’s been sitting in your closet, we have the tips you need. The buttoned blouse’s clean lines and timeless silhouette give a vintage flair to our beloved midi, forming a classic and extremely versatile complement to any midi skirt look.

Wearing a buttoned blouse to style a midi skirt can be done one of two ways:

  • For a more traditional style, button it as usual and tuck it right into your midi skirt. 

  • For something slightly more casual, button the blouse only partially down the front, tying the lower ends of the blouse front together as an adorning knot or bow. 

Both styles accentuate the waist in an overwhelmingly flattering manner, à la Audrey Hepburn in Roman Holiday

#3 With Boots

While midi skirts can sometimes be known as a somewhat more demure style, slipping on a pair of boots alongside your skirt can embolden your whole look. Boots' heavier, chunkier soles can add structure to your skirted silhouette in a way that a sandal or ballet flat simply couldn't. 

Since midi skirts fall below the knee and most boots tend to as well, it can sometimes be tricky to know exactly how to style midi skirt looks with boots. Just like there are many boot styles, there are many different ways to best wear them with a midi skirt, especially depending on your height and/or body type. The examples below can give you styling inspiration best suited to make your skirted boot-stomping the best for you, your comfort, and your look:

  • Tall boots – The midi length skirt has long intimidated the world of petite fashion, but with a tall boot, any petite woman can appear tall and confident in a midi dress or skirt style. Since a tall boot (like the strut-stunning knee-high variety) disappears into the midi skirt, there are no visible edges that "cut off" the leg in unflattering proportions. The seamless transition between boot and skirt makes for an ultra-tall appearance, and bonus points if the boots have a nice heel!

  • Chelsea boots – The Chelsea boot hails from the same 1960s London fashion scene as the midi skirt, so it’s no wonder the two are a natural and beautiful match. The Chelsea boots sleek and sporty silhouette, shiny leather exterior, and high, structured ankle shafts make it an elegant boot on its own. When sitting below the hemline of a midi skirt, ankle boots bring not only their classic elegance but also an overall edge to your outfit. Opt for a flat sole to lean into the androgynous edge, or add a heel or lug sole to give chunky contrast.

#4 With Tights Underneath

This pairing provides the most visual interest in your midi skirt outfit with what we find to be the littlest effort. Layering tights underneath your midi skirt capitalizes on the extra leg space its cropped hem gives you and thus opens the door to an array of endless styling options.

If you're donning heels with your midi skirt, a sheer black pair of tights can really push your outfit's aesthetic into the realm of old Hollywood glam. Tights and ballet flats and a midi skirt, on the other hand, harken back to London twee, a delicate and feminine sense of fashion. And, a petite style pro-tip: no matter the shoe, matching your tights’ color to your shoes creates an elongating illusion effect.

You can also use patterned tights to lend your outfit an unexpectedly fun and exciting visual element. Opting for more "neutral" patterns of tights—micro polka dots, back seams, fishnets—allows for a subtler way to try out this style touch. Or, try brightly colored or glittery tights for an eye-catching shock of vibrancy. 


woman wearing black midi dress

#5 With a Blazer

A skirt as smart as the midi deserves a jacket that can match it in style, versatility, and sophistication. Enter the blazer. 

Blazer jackets have long been paired with the office-famous pencil skirt, but it's with the midi skirt that the blazer jacket really hits its style stride. The structured square edges of its shape stand out against the softness of a midi-length dress or skirt, especially if there's more fabric gathered. This elegant and trendy piece can be a new staple and can replace your black leather jacket from time to time.

Though leaving the blazer open, bold, and powerful is a worthy look unto itself, there's ample room to modify this look with some playful creativity: 

  • Add some whimsy to the blazer's stark, powerful style by adding a belt over your blazer at your natural waistline. This softens the jacket's edges, incorporates another style element, and has a charming leg-lengthening effect.

  • Roll or push your blazer's sleeves up your arm to "dress down" the more sophisticated blazer and midi skirt combo. Finish off the outfit with a comfy t-shirt under the blazer and casual sneakers for an easy day-to-night look. Just swap out the kicks for heels!

From cropped blazers to linen blazers to vintage, one-of-a-kind styles, there’s not one that wouldn’t complement that charming mid-calf hemline. Even an oversized blazer-style coat would be a great styling complement to a midi skirt, especially in the colder months. 

Karen Kane: Curating a Wardrobe of Classic California Chic

A single midi skirt added to your wardrobe can bring maxi style benefits to your everyday fashion rotation. From warm seasonal looks to eccentrically accented styles, you can build midi skirt outfits to suit an assortment of various fashion tastes and stylistic aesthetics. 

At Karen Kane, we’ve crafted dozens of styles that not only complement classic looks like the midi skirt, but also make you feel your best. Our spring selection features everything from the flowy midi-length pieces we know and love to the cozy cable-knit cardigans and breezy springtime tops that pair with them. No matter how you choose to style your midi (and mini and maxi and beyond), Karen Kane’s collection offers the perfect carefree and comfortable California spirit that will have you looking and feeling your best.



Vox. The surprisingly controversial history of the midi skirt.

The Atlantic. The Midi Skirt, Divider of Nations.


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