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They Say Women Over 50 Shouldn’t Wear Certain Styles, But I Couldn’t Care Less

“My cute daughter-in-law is wearing a skort,” said my mother-in-law, who had just come to town, during an I-arrived-safely call to her sister. “Isn’t that something? Ayla wears skorts too.”

Ayla was 6 at the time.

I remember stifling a sigh. Clearly I had done it again — worn something she thought inappropriate for a 40-something woman.

But her words didn’t sting. Heck, it was more polite than the gawks I received from some passersby or the giggles I was certain pre-teens directed toward me.

“So, it’s good to be here,” she said, scanning my outfit as we sipped coffee after the call. That’s before she stated what was on her mind: “Huh….I could never be comfortable with that much skin exposed.”

At that time in my life, I was obese. Not plump. Not pudgy. Obese. And I figured I’d garner gawks and giggles no matter what I wore.

Have you ever seen an obese woman dressed in long sleeves and pants during a 100-degree, drippingly humid day? Of course you have. Does the outfit hide her heft? No. She looks obese. And hot. And embarrassed by her size.

When I gained so much weight I had to carefully choose where I sat, I vowed I would never join the covered-from-head-to-toe sorority. First, I liked comfort and cleanliness too much to tromp around with my hair plastered to my head by sweat and giant perspiration stains on my clothes. Second, I knew I was fat and there was no way to hide it.

how to dress well in your 50s

(Photo courtesy of Nancy Dunham)

Not that I didn’t try. I donned a long black dress when I hit my all-time weight high, convinced it made me look thinner. One look at a photo snapped during a wedding (yes, I wore black to the ceremony; delusion is ugly) showed it didn’t.

Sure, I was embarrassed I was so large, but buying shapeless clothes wouldn’t erase that.

The other reason I chose clothes without something akin to abandon was that I have always loved having a distinct fashion style. In high school I wore short sassy skirts, cute suits with nipped waists, and patterned hose. I remember joyfully saving until I could finally plunk down the cash that made the multicolored sweater, sky-high heels or adorable skater skirt mine, mine, mine.

In college I went through a bit of a hipster-punk phase, then started my career on a Banana Republic-meets-Annie-Hall kick. I didn’t spend all of my pay on clothes, but enough that I ended up walking to work more than driving. It was worth it.

How to Dress in Your 50s

When the pounds started to pile on in my late 30s and early 40s, I was devastated. There were no attractive clothes that fit. Everything I found made me look like a polyester-tangerine, decades older than my actual age.

When I finally found a few online retailers that offered contemporary clothes for the “plus-sized woman” (I loathe that term) I bought. Wearing the funky outfits, even if they were in the largest sizes possible, boosted my confidence as nothing else had. I laughed more. I went out more. I began to really enjoy life.

But candidly, fly outfits in extra large sizes weren’t always easy to find. Even specialty stores that stocked some were awash in polyester pantsuits.

You can imagine my joy when I lost 20 pounds, 40 pounds, 50 pounds, 80 pounds, 100 pounds. Each time I lost 10 pounds I was as excited as a child. Soon it was no more “plus- size” retailers for me. I could shop anywhere.

The first time I just walked into a boutique and actually fit into the clothes I felt like grabbing a megaphone and shouting my joy. When I went to pay, I half expected a ticker tape parade to commence. I was thrilled – I could buy the clothes I’d loved from afar.

Now there are some clothes I would never consider wearing, especially now that I’m fighting to lose the 20 pounds I gained (and I am losing it!). Crop tops, leather pants, sky-high heels, glitter? No. But skorts, long earrings, some leggings, kimonos, booties, lace-accented skirts? Bring them on.

how to look younger in your 50s

(Photo courtesy of Nancy Dunham)

Yes, I’ve read all of the blogs and articles that discuss dressing “your age.” But my thought is if something fits me — and of course doesn’t look like I’m pretending to be a teen (again — no to crop tops) — I like it and it’s comfortable, why not buy it?

“But you’ve always dressed like that,” said my best friend Lisa. “It’s just who you are.” After 30 years of friendship, I guess she’d know.

And now that I mentally flip back through my punk-funk years, glam years, western apparel years, preppy years, obese but stylish years and now, I realize following my own style guide is what made me truly comfortable in my own skin.

So, how to dress in your 50s? Feel free to say a 50-something woman — yes, I’m there now — should leave large hoops earrings, skorts, or leggings to the millennial crowd. This 50-something woman wears what she likes — and feels good doing it.

This essay was written by Nancy Dunham, an award-winning freelance journalist based outside Washington, D.C.

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