The Long and Short of Dressing Your Age

Inappropriateness is often in the eye of the beholder

Short dresses and short shorts are popular again this season, and I'm so happy! I like the look, especially for summer, and still have good enough legs that I feel comfortable wearing them ... on most days. Every now and then, though, I'm confronted with the following question: "Is this the way a 57-year-old woman should be dressing herself?"

Many of us who consider ourselves to be enlightened like to proclaim that "a woman should feel free to wear whatever she wants," and I mostly believe that.

However, we can all recall times when we've seen an older lady dressed in an outfit that was just wrong — not because it was ill-fitting, but because it looked way too young, like it belonged on a teenager.

I know, who am I to decide what's "way too young?" It's hard to say, but I kinda know it when I see it (and I know you do, too). But the thing is, I don't want to be that woman. I don't want to judge another woman because she has chosen an outfit that I've somehow determined is unbecoming to her age.

In general, my attire tends toward stylish but not too trendy. I like to look good, but I'm a lazy shopper, so I need clothes that will work for many seasons. I can’t be bothered with an item of clothing that has a short shelf-life.

And that’s why I actually might have been that inappropriately dressed woman a few times, though I don’t like to admit it. The downside of staying pretty much the same size most of my adult life is that I can still fit into clothes I wore many years ago. At one point, I think my girlfriends were going to do an intervention if I didn’t stop wearing my beloved daisy dukes (very short, cut-off denim jeans, for those unfamiliar with the term.).

Rather than admit that I was a little long in the tooth for shorts that short, I decided that they were just jealous because they could no longer fit into theirs. I eventually and reluctantly agreed they might be right, and retired my shortest shorts … kind of. Now I wear them only on vacation, where nobody knows who I am.

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I've always loved shorts, short skirts, short dresses. But then, at one point, I thought I should start wearing my hemlines at a more "respectable" length. I decided that if I was going to shake my head at other women who looked like they’d been shopping in the juniors department, then I should stop being one of them. I convinced myself that they looked foolish, but I looked cute. It was getting tough, however, to keep up this self-delusion.

When I recently started a new job, I used that as an excuse to try out a new look. I bought myself a few skirts and dresses with hemlines designed for grownups. Hated it. Too matronly. Too boring. Like I lost my swag, and I couldn't have that. So my hemlines started to creep back up — not quite to mini length, but up above my knees. Where they belong.

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