What to Wear with a Maxi Skirt Over 50!

Today, I am joining Mary Ann to talk about maxi skirts! Mary Ann is petite, and I am tall, yet we both share a love for maxi skirts and dresses. What to wear with a maxi skirt over 50? Spoiler alert: everything!

Maxi skirts are so versatile. 

Maxi skirts can be worn from casual to formal. They can go from day to night. Maxi and midi skirts are the most versatile pieces of clothing in your wardrobe. I no longer wear shorts unless I’m at the pool or beach, but skirts, yes, all the time. 

The history of maxi skirts

Maxi skirts were popular in the 1960s and 1970s, and then again in the 1990s. What I love about their popularity now is that anything goes. Wear it with a blazer or an oversized T-shirt, and everything in between! 

I recall a Ralph Lauren plaid wool maxi skirt that I wore in the 1990s, paired with a denim shirt and a black turtle-neck sweater. I wore it with black riding boots and felt so chic. I wish I had that skirt, but I do still have the riding boots. Remember those? 

What makes a skirt a maxi skirt over a midi?

Well, if we are getting technical, a maxi skirt typically reaches the ankle or the floor. Since I am 5’10”, I rarely find a maxi skirt that touches the floor. So, maybe most of the skirts I’m wearing would be more of a midi skirt. A midi skirt falls between the knee and ankle. 

Organic Linen Bias Skirt from Eileen Fisher

Left: Organic Linen Bias Skirt, Organic Linen Jersey Crew Neck Tee, and a white Oxford shirt. Right: Organic Cotton Poplin Cropped Shirt, Harlow Leather Oxfords, Luna Sunglasses, Acetate Apple Watch Band.

This is a great all-around skirt from Eileen Fisher. It’s available in four neutral colors. I’m wearing the branch color. The brown or branch color is as versatile as black. It looks good paired with black, white, chambray, or denim. 

I also have the Organic Linen High Collar Jacket in the branch color. I like to have options when traveling, and this skirt and jacket were worn multiple ways on our recent trip to France. 

Eileen Fisher Organic Linen Bias Skirt and High Collar Jacket in the color Birch. Worn with an Organic Linen Jersey Crew Neck Tee and Harlow Leather Oxfords, also from Eileen Fisher. Accessories: Luna Sunglasses, Acetate Apple Watch Band, and Leather Crossbody Bucket Bag

A poplin maxi skirt from Quince

Left: Organic Cotton Poplin Cropped Shirt, Organic Cotton Poplin Maxi Skirt, Harlow Leather Oxfords, Leather Crossbody Bucket Bag, Caddis Prescription Glasses, Right: Kule Striped Modern Tee, Leather Penny Loafers.

This poplin maxi skirt is a must-have for your summer-to-fall wardrobe. I love the poplin fabric that is cool to wear on hot days, but still looks somewhat crisp. I wear it with everything from a GAP tee (sold out, similar to this one from Kule) to a black poplin shirt or this split-neck top in black.

Everywhere we went in Paris, I saw women (even on a hot day) wearing all black. Cotton poplin is the perfect choice, looking good from morning to night. 

Footwear with maxi and midi skirts

I wear sneakers with a midi skirt, but I never wear them with a maxi skirt. I do, however, only wear flats. I am forever watching what people wear in NYC and Paris, and footwear is always on my mind. I have always worn oxfords and loafers, and now they are trending. 

Oxfords

Before our trip, I ordered this pair of oxfords from Elieen Fisher, and they are the most comfortable shoes. Right out of the box! I usually reserve that phrase for Adidas Sambas. I was hesitant to bring a new pair of shoes on a trip, but they turned out to be the perfect supportive shoes. I wore them with skirts, jeans, and these summer twill pants from Alex Mill.

Loafers

Women in Paris love oxfords. I noticed it last September, but even on hot days in the city, where temperatures were in the 90s, women were wearing their loafers with everything from long skirts to short skirts, dresses, shorts, and jeans. I wear these from The Office of Angela Scott. A traditional loafer in black that goes with everything. 

Gucci loafers cannot be beat for comfort. Expensive, yes. But worth every penny. If I were to conduct a cost-per-wear analysis for my black Gucci loafers, I’m sure I could get it down to about $1. I love wearing them with skirts of any length when I know I want total comfort. 

Allison Walsh of That’s Not My Age often pairs loafers with skirts and has recently posted some fun colors. For summer, I think a pair of these would brighten up an all black outfit! 

What to wear under your skirts, especially in the summer!

Shapewear… no, thank you!  Cooling shorts! Yes! I love these from Thighsociety. They come in several colors and are available in three lengths. I tried one pair in the almond color and the 7″ length. I washed them every day, because once you wear them, there’s no way you want to go back to regular undergarments under skirts. 

Now that you have my perspective on wearing maxi/midi skirts as a tall woman, let’s see how Mary Ann, who is petite, wears her maxi dresses.

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