How to Wear a Midi Skirt over 50

How to wear a midi skirt over 50, or at any age! I’m joining Cindy and Mary Ann today to discuss midi and maxi skirts and dresses. Lately, I have been loving all the options for midi skirts. They can be worn casually, like a pair of shorts, or dressed up for any occasion.

The skirts I wear today can go from day to evening with a simple change of shoes and a top. Add some jewelry like bangles for day or night. Silky midi skirts are perfect for travel!

Inspiration from Alyson Walsh

Alyson Walsh, author of “That’s Not My Age,” has several recent examples on Instagram where she is wearing a midi skirt with sneakers (or trainers), oxfords, and casual sandals and looks amazing! Although Alyson does wear heels, she is no stranger to wearing flats. And, of course, it’s these looks that interest me most.

What I love about Midi skirts is how versatile they are for any look.

I loved my brown print silky midi skirt from J. Crew and wore it so much that I went back and got it in black. The black skirt could easily be dressed up, but mostly I plan to wear it casually. I do love to have options, though. Especially when I travel, I may need to dress up a little more than I had planned, and a black silky midi skirt gives me that option. But always worn with flats no matter the occasion.

Ballet Flats are Back in Style!

Thank goodness. I have always worn flats, maybe because I’m 5’10″– but mostly I just prefer the look. Even when I was much younger, I would always wear flats. My daughter Madeline is 5’6″ and prefers flats. She wears loafers and sneakers with dresses over heels and looks adorable. At 61, I can say that I will never wear heels, ever. And with so many beautiful choices for oxfords, ballet flats, and loafers, sandals, there’s no need to worry!

ICYMI: ballet flats are one of the biggest shoe trends for summer 2023! Marie Clair calls them “sweet, stylish, and easy to slip on and off.” So if you are like me, you probably have at least one pair of Tory Burch ballet flats in your closet, and maybe even in the original pink and orange print box!

Now is the time to bring them back and wear them with your maxi and midi skirts! I”m wearing mine with a CP Shades black maxi skirt, a black tank, and a black blazer. Maxi dresses can be tricky at my height, so I prefer to wear maxi and midi skirts and keep the top the same color to look like a dress; then, I can add a layer like a shirt, sweater, or jacket.

Boyfriend Shirts

Boyfriend shirts are a little oversize, making them perfect for wearing with midi or maxi skirts. You can wear it open over a tank (I love these high-neck tanks from J. Crew) or wear it tied at the waist or tucked in. Zara has several menswear-inspired shirts. The black, gray, and white stripe is from Unsubscribed, which is a new brand for me. Have you been to an Unsubscribed store? They only have a few, and three of them are near me. NYC, East Hampton, Westport, CT, Greenwich, CT, and Palm Beach.

Midi Skirt with a denim Jacket

I shared the Gwyneth skirt from J. Crew in this post and continue to wear it often! On this day I wore it with a high-neck tank in brown with a brown skirt. I like the one-color base, and then I added a denim jacket, brown oxfords, and a hand-knotted rope tote for summer!

The Perfect Midi Dress from Quince

This dress from the brand Quince is the perfect transition dress from summer to fall.

Let’s see how Cindy and Mary Ann wear midi and maxi skirts!

Cindy Hattersley Design

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