Fashion Sense

There is a woman at my office, M, who is very sweet, if occasionally flutterbrained. She's about ten years older than me, and has a daughter who just started college.

Here's the thing. She dresses like she's still 25. Flirty mid-thigh-length skirts and shirts built to show cleavage.

And it just doesn't work. She's tall and slender and fit and it ought to work, but... She spent too many years as a sun-worshiper in California and now the skin she's showing off is permanently wrinkled and loose-looking. Worse, it seems to collude with her occasional flights of bubbleheadedness to make her seem even blonder than she already is. I mean, when she wears jeans and a t-shirt on a Friday, she actually seems more competent and professional than when she's wearing her nicer clothes the rest of the week. Even her haircut feels to me like someone who's trying to deny that they have a daughter in college, though I can't quantify why.

I'm trying to figure out exactly what buttons it's pushing for me, and why, because I'm not that much younger than her, and thanks to the miracle of weight loss, my skin is even looser than hers. When I wear a V-neck sweater, even if I'm looking hotter than I have at any time in the last fifteen years or so, do I still look kind of pathetic?

How do other people figure these things out? I know women who always, always, always look perfectly put-together, no matter where they are. Not just perfectly put-together, but appropriate to their surroundings and roles. Competent and knowledgeable and attractive (but not on the hunt). And it's not about body size, because they run the gamut from tiny little size XS ladies up to women as big as I've ever been. And I can't, for the life of me, figure out what makes the difference.

It's knowing what clothes to choose, and what accessories, and what makeup, and what hairstyle -- not only knowing it, but being comfortable inside it. It's a sense of fashion and style that I somehow missed learning. I'm not sure it can be learned, but I keep trying.

Every time I encounter one of these women, I find myself trying to dissemble the pieces and figure out what makes them work. And every time I encounter someone who doesn't work, I try to figure out why. How is it that S and B, who were both larger, older women, always wore similar outfits, but S looked like a high-powered executive and B always looked faintly rumpled? Why can 50-something J wear flirty 20ish clothes and look cute, while 50-something M looks like she's trying too hard? I can't tell the difference, and I'm pretty sure that means I'm on the wrong side of the equation, here.