Would you consider this weird, try-hard or just anything like that?
Most Helpful Guy
It should look fine... if you own the look.
If you're wearing it doubtfully and awkwardly walking around with it, it will suck. But, wearing it while knowing it looks good on you... That should make the difference.
Most Helpful Girl
I'm sure it would be adorable! If you feel weird about it, try wearing it with denim (especially distressed denim!) first to keep it casual. Then dress it up with a skirt when you're comfortable with it!