21. Lena Dunham
I feel like Lena could maybe pull off this outfit nowadays, honestly.
20. Paris Hilton
Paris is looking surprisingly responsible right here.
19. Miley Cyrus
Miley’s getting upstaged by her dad’s mullet here.
18. Macklemore
THAT HAIR. THOSE FRECKLES.
17. Gwen Stefani
Gwen apparently hadn’t started showing off her killer abs at this point.
16. Victoria Justice
Victoria was mean-muggin’ as a baby.
15. Tegan and Sara
This is honestly, ridiculously adorable.
14. Jessica Biel
A+ doily neckline, Jess.
13. Cindy Crawford
Cindy’s posing skills were always on-point.
12. Drake
Drake has always been a teensy bit dorky.
