Harry Styles

Aww! We almost forgot how adorable a younger Harry Styles looked with his signature floppy hairstyle. After all, he’s come a long way in terms of his personal style and career since this prom photo was taken. If only this Harry knew what the years that followed had in store for him.

He became part of the British boyband One Direction in the early 2010s and enjoyed immense success for the better part of that decade. Styles, now $80 million rich, saw his solo career prosper, too. His single Watermelon Sugar topped the Billboard Hot 100 in 2020.

Shailene Woodley

Shailene Woodley was only 16 when she got her breakout role in the teen drama The Secret Life Of The American Teenager. So, when she attended her own prom wearing this figure-hugging gown, she was already quite famous. But her star has only shined brighter since.

She scored her film debut in the 2011 movie The Descendants, then bagged the lead part in the Divergent franchise. Woodley, who announced her engagement to NFL star Aaron Rodgers in 2021, last appeared in the romantic film The Last Letter From Your Lover.