Kate Upton
This outfit is actually perfectly nice on her. She LOVES wearing black, to a fault I think; some stylist could make a mint off legitimizing her as a fashionista with just a few tweaks. She's not BAD, necessarily? Just unimaginative.
One tweak: fit. Her poor chest is leaking right out of this.
Alexandra Daddario
Alexandra here is the other actress in this love triangle -- the man is Matt Barr, most notably the dude who pretended to be Peyton's brother on One Tree Hill and then locked her in the basement -- and if that isn't Self Portrait, then it's a dead-on parody of one. Although sometimes Self Portrait already feels like a parody, of itself or any number of other things. Her boobs look like potholders that someone's aunt made, for example.
I also think she needs a different makeup artist. This isn't as stark, but: She's got very fair skin and those stunning icy eyes, and for whatever reason even a very little bit of makeup seems to read as a lot on her face... so a TON of makeup is like she's a four-year old let loose in her mother's bathroom. I think a more delicate approach might be required, because I never feel like I'm looking at HER, as much as at a cosmetics counter.