Some of them were always gorgeous. Some started out awkward and grew into beauty. But one thing connects these celebrities: As they’ve grown older, they all seem to be more comfortable in their own skins.
We might not have access to the same makeup artists and stylists, but we can all learn a thing or two about growing older with grace, humor, and self-confidence.
21. George Clooney
George was not the handsomest of young men. When his hair started to go gray, he transformed from a late 80s goofball to a silver fox worthy of carrying on Cary Grant’s Hollywood legacy. (He’s also the charmer with the bowl cut in the header picture!)
20. Will Smith
Who would have guessed that the Fresh Prince of Bel Air would grow up to be one of the biggest movie stars on the planet—and a fine-looking family man, too? He still has his signature charm, but it’s balanced by a newfound gravitas as he’s gotten older.
19. Demi Moore
Look, the 80s weren’t kind to anyone. But Demi’s crimped hair and over-the-top makeup are cringeworthy even for that decade. She ditched all the extra bells and whistles, and she’s all the more beautiful because of it.
18. Dwayne “The Rock” Johnson
Has there ever been a bigger Cinderella story than The Rock? From nerdy teen to pro wrestler to charismatic movie star, he just keeps getting better with age!
17. Angelina Jolie
Angelina was always beautiful, but there’s something about her calm, radiant smile now that makes her even more stunning. Losing the blonde dye job helped, but her role as a mom and humanitarian really seems to suit her.
16. Gabrielle Union
Gabrielle is a vampire, right? That’s the only explanation. She has not aged a day since Bring It On. Some celebrities get better with age, but Gabrielle hasn’t changed at all since she was in her 20s.
15. Bruce Willis
When he stopped fighting his receding hairline and decided to shave it all off, Bruce went from an average guy to a red-hot movie star. Maybe more men should follow his example and embrace the baldness.
14. Justin Timberlake
Speaking of radical hairstyle changes, Justin’s crispy-looking frosted curls were a fashion disaster. He went solo, cleaned up his look, and he just keeps getting better with age.
13. Sarah Michelle Gellar
She’ll always be Buffy to her fans, but Sarah Michelle has come a long way since her teenage stardom. In addition to raising some seriously cute kiddos, Sarah started her own baking kit business to help families learn to cook together.
12. Daniel Craig
To be honest, I didn’t recognize Daniel’s “before” picture. The too-blond hair washes him out, and he needed another decade (or two) to settle into his rugged good looks.
11. Sandra Bullock
Sandra has always been one of America’s Sweethearts, and although she’s been in the spotlight for more than 20 years, she just keeps getting better with age.