I agree that it's all in the styling. You look great in short shorts, short skirts, or anything that shows your legs -- that's not the issue. So if you love it, go for it.
I have a friend in her late 50s who wears skirts almost that short. She is tall, slim, and rock n roll. She doesn't look like she's "trying too hard" because that is her style. She has wacky dyed hair (with a pink streak), a beat up moto jacket, and fake tattoos that she switches up all the time. (They are usually funny).
She's an artist. But also a professor. Head of a department, no less.
Now...admittedly, she could not get away with this if she had another job. And while she doesn't look like she is "trying too hard" she sometimes does look...frankly...a little kooky. Personally, I like her kookiness, and most other people do as well.
From what I know, you wouldn't look kooky. You'd look like yourself. But yeah...it's got to be a look you can own, and feel confident in. Which is maybe the biggest issue. If you can't sit comfortably and need to be adjusting yourself all the time, that's not a good idea.
