7 Midi Skirt Outfits For Women Over 50 For Every Occasion, From Errand-Running to Cocktail-Sipping

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We spent our 20s and 30s showing off our legs in mini skirts and graduated to flowy 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 for women over 50.

Why choose a midi skirt?

Amanda Holden in a brown midi skirt outfit
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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, 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
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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
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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 will be sure to turn heads no matter where the day takes you.

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

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If you've been wanting to try out the leather trend, a brown leather midi skirt is the perfect way to start. The A-line style won't feel restricting, making it a breeze to move and walk in. Pair it with a simple black long sleeve sweater or top you already have in your closet, and finish it off with black pointed toe booties. To add some flair, add a cheetah print bag. "The mix of hard and soft fabrics creates a nice juxtaposition for bold texture," says Katsanis.

Shop the look:

Brown leather midi skirt: Buy from Ann Taylor, $139

Black long sleeve sweater: Buy from J. Crew, $89.50

Cheetah crossbody bag: Buy from Amazon, $55.86

Black pointed toe booties: Buy from Banana Republic Factory, $62.50

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

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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. A button down offers multiple different ways to wear it, from buttoned up to left open over a white top and more, while matching silver shoes add color balance. Pair it with your favorite black and silver accessories for a look that wows all night!

Shop the look:

Black sequin midi skirt: Buy from Abercrombie & Fitch, $59.99

Silver top: Buy from Lands' End, $69.95

Silver heels: Buy from Mango, $69.99

Black and silver clutch: Buy from Amazon, $48.28

Black and silver clover bracelet: Buy from Amazon, $12.57

Black earrings: Buy from Amazon, $14.99

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

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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 satin tank and throw on a cropped white blazer for a conservative yet chic office ensemble. Accessorize with comfortable flats and gold jewelry.

Shop the look:

Plaid midi skirt: Buy from Vineyard Vines, $87.99

Gold satin cowl neck tank top: Buy from Boston Proper, $70

White blazer: Buy from Abercrombie & Fitch, $54.99

Brown flats: Buy from Rack Room Shoes, $32.50

Gold earrings: Buy from Amazon, $13.45

4. Midi skirt outfit for running errands: Choose stretchy

casual midi skirt style
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 mid made out of jersey material! 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 comfy bodysuit and navy and grey purse add dimension to the look. Keep the look casual with a pair of white sneakers and chunky silver earrings.

Shop the look:

Grey jersey midi skirt: Buy from Uniqlo, $39.90

Navy bodysuit: Buy from Aerie, $49.95

White sneakers: Buy from Amazon, $60

Silver earrings: Buy from Amazon, $13.98

Navy and plaid purse: Buy from Amazon, $30.98

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

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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 pops of pink from the skirt to your earrings then balance out the bold color with a neutral sweater, like this ivory mock neck, and a pearl necklace and slingback heels. A gold belt around the waist will add shape to the sweater and skirt combo.

Shop the look:

Satin pink midi skirt: Buy from Amazon, $24.99

Ivory mock neck sweater: Buy from & Other Stories, $69

Pink drop earrings: Buy from Anthropologie, $32

Pearl necklace: Buy from Amazon, $9.99

Gold belt: Buy from Amazon, $14.99

Pearl slingback heels: Buy from Zara, $79.90

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

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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 asymmetrical bottom hemline for added texture and dimension) and slip into a pair of kitten heels for a bit of height while remaining comfortable. Finish it off with an emerald bag and gold, black and pearl statement earrings.

Shop the look:

Green midi skirt: Buy from Venus, $49.90

Black sweater: Buy from NA-KD, $34.99

Black polka dot heels: Buy from JCPenney, $79.99

Emerald green purse: Buy from Amazon, $30.99

Gold and pearl dangle earrings: Buy from Revolve, $35

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

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Denim never goes out of style — and now, the classic material is popping up everywhere, especially in midi skirts! We love this one because of its dark 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 Petal & Pup, $69

White T-shirt: Buy from Old Navy, $16.99

Jean jacket: Buy from Banana Republic Factory, $36

Tall black boots: Buy from Famous Footwear, $79.99

Black shoulder bag: Buy from Amazon, $16.98


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