These days, as a grandma many times over, I often find myself second-guessing what to wear

I was walking to shul recently when I passed a woman standing outside an apartment building, speaking on her phone with her back to me. She looked tall and vigorous, although the braid hanging down her back was snow white. When she turned around, I was surprised to see she had the wrinkled face of an old woman. She was at least in her late seventies. But what truly struck me was the way she was attired: Like a teen on her way to the beach.

No, I thought. Just: No. A woman that age has no business dressing like that.

The image stuck with me because these days, as a grandma many times over, I often find myself second-guessing what to wear. I’m like an adolescent trying to figure out (or arguing with her mother about) whether she’s old enough to wear high heels and makeup. Except now, at the other end of the cycle, I’m trying to figure out what not to wear. Like maybe not stilettos or puffy skirts. On the other hand, I still crave a little pizzazz! I don’t want to be totally out of the style loop, even if I’ve forsaken high heels at simchahs.