Ferris Bueller's Day Off : I always thought Jennifer Grey-

Made this movie after Dirty Dancing however timeline shows she made this movie before. She definitely looked alot better in Dirty Dancing. In this movie, she looks......harsh and much older even.

Although I don't fully agree with you, I will say time period might play a role in that. Dirty Dancing was set in the early 1960s, so her look and wardrobe were very different from the 1980s backdrop of Ferris Bueller. I would also argue that her character being so completely different in each movie contributes to differences in how she comes across physically.