What Does it Mean to ‘Dress Your Age’?

What to wear as you age is a highly personal decision, our critic writes, but certain garments still come with associations and assumptions.

I have always dressed fashionably. I still want to, but, as I get older, I don’t want to look silly in an outfit for a 20-year-old. For example: Right now I’m wondering about pants. Everything seems to be really, really wide and ballooning. I like them, but they aren’t the most flattering. What about hemlines? Should they be long or short? Are there rules to dressing as you age? — Liz, Akron, Ohio

This is a question I ask myself a lot. After all, just because you can

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