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7 Midi Skirt Outfits For Every Occasion From Errand-Running to Cocktail-Sipping

Discover how the mid-length skirt style can flatter your body type

We spent our 20s and 30s showing off our legs in mini skirts and graduated to flowy, trouble-spot masking maxi skirts in our 40s, but there’s a new style of skirt currently trending and that uber-stylish celebrities like Amanda Holden, Jennifer Garner and Kate Middleton have been spotted sporting recently: the midi skirt. Curious about the style and want to try the trend but are unsure where to start? We asked celebrity stylist Anna Katsanis (who has worked with Jessica Chastain) and fashion expert Melissa Rivers (yes, Joan’s daughter!) to explain what makes this skirt-length so flattering, how to wear it and the best tips to putting together midi skirt outfits for any occasion.

Why choose a midi skirt?

Amanda Holden in a brown midi skirt outfit
Amanda Holden, 52Neil Mockford / Contributor/Getty

Midis are one of the most versatile skirts you can own: A perfect in between of the mini and maxi, midis hit just a few inches below the knee. This length offers the coverage of a maxi (great for hiding trouble spots and keeping legs warn on colder days), but like a mini, still gives a glimpse of gams, albeit tasteful peeks of the lower calf and ankle. The skirt type is so versatile, it can easily be dressed up or down. Plus, they are a chic way to look polished and put together, with very little effort put in. All reasons why women of all ages are absolutely loving the style.

“I love the clean lines (of a midi skirt),” says Katsanis. “I love how effortless and minimal they look and how they can make an outfit feel very polished and elevated.”

Jennifer Garner in a midi skirt
Jennifer Garner, 51Gotham / Contributor/Getty

Also great: A midi skirt is appropriate for any age, it’s light and breathable, making it even more comfortable than many pant options. Plus, adds Rivers, “they come in A-line, pencil, pleated, slip, etc., allowing women to choose the best silhouette that suits her body type and personal style.”

Katsanis agrees, adding, “For an older woman it creates a more put-together, finished look. They can be professional, dressy, classic or elegant depending on how you style them. They are also good for anyone who may not be comfortable or feel appropriate showing too much skin.”

What to look for and avoid with midi skirts

Kate Middleton in a midi
Kate Middleton, 41Neil Mockford / Contributor/Getty

Although usually easy to find and wear, there are a few suggestions stylists advise you follow when it comes to midi skirts. Keep body shape in mind. “Midi skirts should create a balanced silhouette by highlighting the waist and falling nicely over the hips and thighs,” explains Rivers.

If you’re full on bottom: “Avoid anything that hits your knees at an awkward length and has overwhelming volume,” says Rivers. A more pencil style midi works best for this shape.

If you’re smaller on bottom than on top: Opt for a more flowy style midi to add balance to the body.

7 midi skirt outfit options: One for every occasion

We put together seven different midi skirt outfit looks that are figure-flattering and will be sure to turn heads no matter where the day takes you.

1. Midi skirt outfit for a night out: Try leather

leather midi skirt outfit

If you’ve been wanting to try out the leather trend, a black leather midi skirt is the perfect way to start. The more form-fitting style shows hugs the body while still being an appropriate pick for a low-key, yet chic night out. Paired with a red cotton bodysuit, floral-shaped clutch the look shows off curves with flirty flair. Plus, “the mix of hard and soft fabrics creates a nice juxtaposition for bold texture,” says Katsanis. Finish it off with leather booties and silver hoops, and throw on a cropped jacket for chillier nights.

Shop the look:

Leather midi skirt: Buy from Express, $52.80

Red one-shoulder bodysuit: Buy from Express, $32.40

Cropped jacket: Buy from Cider, $36

Red clutch: Buy from Amazon, $25.99

Silver hoops: Buy from Amazon, $9.93

2. Midi skirt outfit for a festive party: Step into sparkly

how to style a midi skirt for a party

Whether prepping for a holiday party or an office soiree, the sparkle of a black sequin midi skirt with a silver top add glitz and glam to help get you in the festive spirit. Picking a blouse with ruching helps slim the midsection while matching silver shoes add color balance for a long lean look. Pair it with your favorite black and silver accessories for a look that wows all night!

Shop the look:

Sequin midi skirt: Buy from T.J. Maxx, $24.99

Silver top: Buy from Zara, $27.90

Silver heels: Buy from Gap, $47

Black clutch: Buy from Amazon, $14.99

Silver bracelet: Buy from Kohl’s, $9.80

Black earrings: Buy from Amazon, $14.99

3. Midi skirt outfit for the office: Look for linear

Work outfit with plaid midi skirt

You might dread having to go into the office, but slipping on a midi skirt helps you look put-together which can help boost your mood. Opt for one with a linear print (which pulls focus vertically to help legs look long) that’s made out of stretchy material (which ensures you’ll stay comfy all day). Tuck in a simple white button-down and throw on a cropped black blazer for a conservative yet chic office ensemble. Accessorize with comfortable ballet flats, gold jewelry and a black tote that holds all of your essentials from laptop to keys!

Related: ‘I’m a Podiatrist and These Are The Most Comfortable Flats for Women Over 50’

Shop the look:

Plaid midi skirt: Buy from Amazon, $25.99

White button-down: Buy from Banana Republic Factory, $28

Ballet flats: Buy from Kohl’s, $79.20

Gold and black watch: Buy from Amazon, $32.50

Gold earrings: Buy from Amazon, $13.45

Black work tote: Buy from Amazon, $33.86

4. Midi skirt outfit for running errands: Choose stretchy

casual midi skirt style

Who would have thought running errands in a skirt could be so comfortable? Someone who obviously never did it wearing a knit midi! The material is lightweight, so you won’t overheat but has ultra-stretch, making it easy to sit, walk or even run in. Navy blue add-ons like a smoothing bodysuit will help smooth and hide any lumps and bumps. Keep the look casual with a pair of white sneakers and chunky silver earrings. Top it off with a navy and grey purse.

Shop the look:

Knit midi skirt: Buy from H&M, $57.99

Navy bodysuit: Buy from Aerie, $34.96

White sneakers: Buy from Amazon, $70

Silver earrings: Buy from Amazon, $12.99

Navy and plaid purse: Buy from Amazon, $30.98

5. Midi skirt outfit for a daytime gathering: Go for bold

date night outfit

A satin midi skirt is all you need to elevate a more relaxed look.The material is elegant and classy, and also lightweight and breathable. Add a touch of feminine flair with a pops of pink from the skirt to your earrings then balance out the bold color with a neutral sweater, like this ivory mockneck, and a pearl necklace and slingback heels. A gold belt around the waist will add slimming shape to the sweater and skirt combo.

Shop the look:

Satin pink midi skirt: Buy from Old Navy, $39.99

Ivory mockneck sweater: Buy from Nordstrom Rack, $59.97

Pink drop earrings: Buy from Francesca’s, $24.95

Pearl necklace: Buy from Amazon, $8.39

Gold belt: Buy from Amazon, $15.99

Pearl slingback heels: Buy from Zara, $79.90

6. Midi skirt outfit for a cocktail hour: Slip on satin

cocktail hour midi skirt outfit.

A cocktail hour is a mix between formal and casual — a dressy in-between. While you know jeans will be too casual, showing up in a full-length dress may be too formal. A midi skirt is the just-right in between. “Opt for more luxurious fabrics for a dressy occasion, like silk, satin or lace,” says Rivers. Stay cozy in a simple black sweater (we love the balloon sleeves for added texture and style that also conceals any upper arm insecurities) and slip into a pair of kitten heels for leg-slenderizing height with comfort. Finish it off with an emerald crossbody purse and gold dangle earrings.

Shop the look:

Green midi skirt: Buy from Venus, $39.99

Black sweater: Buy from Express, $59.99

Black polka dot heels: Buy from DSW, $59.99

Emerald crossbody purse: Buy from Victoria’s Secret, $64.95

Gold and pearl dangle earrings: Buy from Francesca’s, $20.95

Related: Cocktail Attire for Women: Dos and Don’ts That Ensure You Turn Heads In a Good Way

7. Midi skirt outfits for a casual lunch: Opt for denim

jean skirt outfit

Denim never goes out of style — and now, the classic material is popping up everywhere, especially in midi skirts! We love this one from Bloomingdale’s, because of its medium wash color, allowing it to be dressed up or down, and its split hem in the front, for more mobility and a hint of lovely legs. A simple white tee pairs perfectly while covering it with a jean jacket keeps the look light yet cohesive. Tall black boots and a black shoulder bag finish off the outfit for a a sleek, polished look.

Shop the look:

Jean midi skirt: Buy from Bloomingdale’s, $98

White T-shirt: Buy from Old Navy, $15

Jean jacket: Buy from Gap, $71

Tall black boots: Buy from T.J. Maxx, $39.99

Black shoulder bag: Buy from Amazon, $42.99

Related: 7 Jean Jacket Outfits That Will Make You Look Stylish and Slim for Any Occasion

For more style inspiration:

The Most Figure-Flattering Ways to Style Flare Jeans for Any Occasion

‘I’m a Podiatrist and These Are The Most Comfortable Flats for Women Over 50’

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