Clearly, the record execs were pandering to a teen audience.
We can see why those who grew up seeing Britney as a goofy-looking child talent might have had a hard time with her sudden transition to sexy tween.
Both international sensations at a young age, it was natch that they stumbled together. You live, you learn.
Britney's pigtails and fluffy writing pen in the "...Baby One More Time" video further play up her youth and innocence.
A lot of people were scandalized that the photographer in question got the seventeen-year-old to take off her clothes in bed for a photo shoot. Britney claims she came out of that one unscathed.
The slightly baby-faced teen look is gone these days, with "femme fatale" taking a full-time front seat.