The story's biggest problem is that it relies very noticeably on the "ugly woman actually just needed to brush her hair" trope, and that makes it unclear why the Renée couldn't simply have put a little more effort into dressing in a way that makes her feel confident without risking a concussion.
The basic conceit of I Feel Pretty is this: a young woman living in New York and pining for the Sex And The City fantasy is dissatisfied with her life and her body, until a freak accident and head injury at a SoulCyle class causes her to see herself as devastatingly gorgeous. With a new expectation of the social privileges she is entitled to enjoy, she changes her life, fueled by the sense that life happens for beautiful people, and she has finally become one.
A generous reading of Amy Schumer's I Feel Pretty would be that it's trying to show that beauty is in the eye of the beholder, and self-confidence is all you really need to make it in the world. Unfortunately, the film goes out of its way to undermine that point at every turn by framing protagonist Renée's confidence as nothing short of an aggressive delusion. Rather than simply approaching her life with a little less pessimism and a little more pep, Renée is shown to take minute, completely unrelated occurrences as confirmation of her self-perceived beauty. She playfully chides a man in a dry cleaner's for hitting on her when he asks for her number... in line. She blows a kiss to a construction worker who whistles as she passes... to a coworker. She thanks a man for his chivalry when he holds the door open... for himself. And so on, and so on.
At first this works. Renée applies for and gets the job she desperately wants, starts dating a new guy who is in awe of her confidence and joins the inner circle of her company's corporate ranks. But she also begins treating her friends poorly and fixating on her looks. Naturally, a second blow to the head interrupts the delusion, leading her to break up with her boyfriend (in a scene so baffling it's difficult to ascertain if the character truly is delusional), abandon a company presentation (and somehow retain her job?) and generally drink herself into a stupor. It's only after discovering that her company is planning to advertise their new diffusion line for "real women" with a straight sized model does she get it together enough to realize that there was no "magic" making her beautiful. She's simply taken her life into her own hands.
The trouble is that I Feel Pretty isn't very clear about what it's trying to say about women, beauty standards and self-esteem. It muddies the message often, and the thesis of the film as it currently stands is something akin to "it's ok to be ugly as long as you believe you're beautiful" which doesn't strike me as the empowering motto it was hoping for. The story's biggest problem is that it relies very noticeably on the "ugly woman actually just needed to brush her hair" trope, and that makes it unclear why the Renée couldn't simply have put a little more effort into dressing in a way that makes her feel confident without risking a concussion. After all, post-SoulCycle, all that really changes is that she wears a little more makeup, clothing that fits, and styles her hair. Amy Schumer is by an standard, a conventionally attractive white woman. Pretending she isn't is insulting to the audience.
There's very little to credit the movie besides a entertaining turn by Michelle Williams as Avery LeClaire; head of the makeup company and sadly afflicted with a baby voice that prevents people from taking her seriously. Lauren Hutton is grossly underused as Avery's grandmother Lily, but she remains radiant as ever onscreen. In the end I Feel Pretty's biggest sin is that it isn't even very funny. A lot can be forgiven by a genuine belly laugh.