No, you don't look hookerish, it looks quite nice. It could look hookerish, but it doesn't. I think it's the tights that make it more nice. Depends what his work people are like really, but I think your outfit is pretty much universal so won't look out of place amongst most people. If they're really really posh, maybe it'll be out of place, but doubt it. Definitely folded down to under or on the knee though, above the knee could end up looking too sexy for a work thing.