While your descriptions are technically correct, I believe that the true way to see them is as a slutty tee.

It’s sort of hard to explain, but the undone buttons implies undressing, yet conceal the naked. Which provokes one to want to see more. There’s some form of erotic of the concealed thing going on.

Anyway, point is, if you think of the henley as a slutty tee, you’ll never go wrong. Wear one with a leather jacket and you’re a slutty bad boy. Wear one just with a pair of distressed jeans in the summer and you’re a slutty blue collar working boy. Wear one with tailored trousers and you’re a slutty playboy.

So when I’m pairing a henley with other clothes, I look at the other clothes and work out what the look is of them. And then I add the word “slutty”. If it feels like a vibe that works, I run with it. If it feels inappropriate (like with a business suit, “slutty businessman” feels lame) I don’t.

P.S. It helps to be hot. But that’s true with all clothing, so whatever.