The Skirt of Perpetual Regret

It's Sunday. Full disclosure time. I'll go first. Then you.

I have what's known as the Skirt of Perpetual Regret.

What’s that, you ask? Oh, you already know. If you're a woman of a certain age, it's either hanging in the back of your closet or folded in a drawer like a sacred scroll. Maybe it's a slinky black number, a tiny skirt, a vintage Levi’s mini, or—God help us all—your wedding dress.

Mine? A small, smug, off-white pencil skirt that once glided over my hips like a silk whisper. Now, getting it past my knees is an act of optimism bordering on delusion.

It represents a time in my life when I had more—

more dreams, more collagen, more stamina, more clothes I had no business wearing but did anyway. It was the era of three-inch stilettos, underwire bras that doubled as armor, and the belief that heartbreak was romantic, not exhausting.

Back then, I was in a rush to get somewhere. Now I look back and realize...I was already there.

And the skirt? It hangs on a velvet hanger, judging me. Whispering, "Remember me? Remember when you wore me to that party and he said you looked like a movie star?" (I did. I wasn’t. But still.)

I try it on every few years, as if my body will magically time-travel back to its pre-cookie era. But life happened—kids, stress, menopause, gravity. Every bite of comfort food and every night spent up worrying about someone I love is now stitched into my thighs. And frankly, I wouldn’t trade that for all the 23-inch waists in the world.

Still, I keep the skirt. Not because I think I’ll ever wear it again—but because it reminds me of the girl I was, and the woman I became. She’s still in there, just with better priorities and orthopedic sandals.

So, your turn. What’s your Skirt of Perpetual Regret? Is it a pair of jeans? A photo? A diary? A dream deferred?

Because here’s the truth: we all have something we keep, not because it fits—but because it meant something. And maybe it still does.

I told you mine, now, you tell me yours...