I do love a classic makeover and my favourites include:
Clueless: Cher making over Tai from a possibly stoned loser into a total betty. The way that Tai has this almost overwhelmed look on her face, taking in the new attention and trying to fit into her new role. Oh and how sad was I when Brittany Murphy died? She was a sparkling presence in Clueless and played the part perfectly.
Bette Davis in Now, Voyager goes from this to this:

It's the perfect illustration of a makeover giving a female character the confidence and damn hotness that she needs to succeed and/or have an affair with a hot guy she met on a cruise ship.
The new series of America's Next Top Model started this week on Living and thankfully it was a double bill so we could enjoy the second episode makeover straight after the first episode. I love that at least one girl always cries, the haircuts either make no sense whatsoever (hello random idea to cut your hair then put a weave on top) or are so bland your mother would suggest it (what you say that blonde hair makes blue eyes pop, get out of here!)
Overall, I think the reason I love a makeover montage is that it illustrates the way that clothes can become either an armour to protect you against the world and allow you to fit in, or they can show everyone your true personality. Like the best makeover cliche - geeky ugly girl whips off her glasses, puts on a cute dress and oh my god she's beautiful! You knew the gorgeous was lurking underneath the dire haircut and tragic clothes but it needed to be framed by a great outfit and good styling.
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