The lipstick is misapplied, going above the lip line ages one's face. Lip liner can help avoid that. Color's not bad, though; at least it's not frosted.
Personally I think Jenn's dress is an improvement. It has built-up shoulder straps, it fits correctly, the empire waist suits her, the color/pattern are not obnoxious, and she seems to be wearing properly supportive undergarments: everything held in when she got up and moved. She's young enough to get away with sleeveless styles. Necklines are a matter of personal taste: when I was Jenn's age, I had long since raised my necklines; but I'm short and I carry my weight differently. Low necklines were tit on me even in my 20's and 30's.
Tim had better start keeping his hands away from his face while on camera. Quit itching your nose, for heaven's sake. That's just rude.