/fa/ - Fashion

>>12385612
Assuming you're talking about moto jackets and the like, because more basic leather jackets can look bad on anyone...

In short? When a woman wears what is historically a mans jacket worn by toughs and outsiders, it's a play on contrasts/contradictions/expectations. The contrast with the female form and wardrobe is interesting, and the greater the contrast (within reason) the better the look. A man wearing a dress is a more extreme example, judged similarly: it is a provocative contrast in form and expectation and tradition, and is judged on that value and not the same way a woman is judged when wearing a dress.

When men try wearing a moto jacket, contradiction isn't at play (though it can be in some cases). Instead they are judged on the basis of how well they pull off the look or how it suits them. The jackets carry a lot of stereotypical baggage, so we still want and expect the wearer to look like someone who is legitimately tough or an outsider. Someone who smokes and drinks and works with his hands and spends more time outside than in (or who goes to bed when everyone else is getting up for work).

It's why Justin Bieber looks silly in a moto jacket, while Kristen Stewart pulls it off.