Bruce Willis then; Bruce Willis now. I always thought he looked silly in his “Moonlighting” years; I think he looks dead hot now.
ETA: A better before. I guess people thought he was good-looking then, but I wasn’t one of them.
Meryl Streep peaked in her 50s (around Adaptation, I think- she was 53). I honestly don’t think she looked good in Manhattan or Kramer Vs. Kramer (cute boobs in Silkwood but I digress), but later on . . . hummina hummina.
I also really prefer a lived-in face with all the lines and wrinkles that accumulate over time; I hate the look of a pulled-back facelift.
Here’s another one . . . Eleanor Roosevelt was an awkward-looking young lady, but a gorgeous old woman.
of course, of course. 
A lot of icons from the 60s and 70s grew into their features: Paul Simon, Woody Allen, Pete Townshend. I saw one of those “Then and Now” photo features for rock stars, and I think Pat Benatar and David Bowie actually looked better later.
George Clooney wasn’t exactly ugly but he sure has improved with age..
And speaking of Anthony Michael Hall, Molly Ringwald really grew up gorgeous.
He is only 35 right now, but if the progression of his looks from wimpy kid to handsome guy continues, in five years Leonardo DiCaprio is going to be drop dead gorgeous.
Winston Churchill
Surely you can’t be serious. There has never been a finer looking crumpet than the young Michelle Phillips. And to say she looks better now…
Am I being whooshed?
Dannii Minogue in the early 1990s: http://www.nowmagazine.co.uk/imageBank/d/Dannii-Minogue-1990s.jpg
And now a fairly recent photo (she’ll be 40 this year): http://www.last.fm/music/Dannii+Minogue/+images/2158057
A completely unnatural progression of course, but I think she’s a good argument that extensive plastic surgery isn’t always horrific.
I say neigh!!
Abraham Lincoln vastly improved his looks after growing a beard at age 51.
Helen Mirren has gotten progressively more beautiful as she’s aged. It doesn’t hurt that she’s also a fantastic actress.
Stranger
A deal that involved giving up her looks?
she is the one i always think of. the older she got the better looking she became.
wonder what alice thought of that.
When Tina Fey got the Mark Twain Prize for American Humor a little while ago, Amy Poehler was one of the presenters. I can’t remember her exact word but she said something to the effect of, “And here’s to looking better in our forties than we did in our twenties”, which is so true for both of them. Both kind of awkward and chubby when younger, now: smoking hot mamas.