In 1998, Teen People released it’s first “Celebrity Style Awards” issue and only the coolest and most stylish celebrities made the cut.
1. Jennifer Love Hewitt: The teen queen of the late ’90s who always looked super cute too in a girl-next-door type of way.
2. Aaliyah: She really was “one in a million.” Only Aaliyah could pull off a bare midriff and tight leather pants and look like an absolute badass.
3. Jennifer Aniston: Great style, but really it’s the hair you wanted!
4. Cameron Diaz: Pretty, funny, and looked flawless in anything she wore (seriously she could have rocked a potato sack) — yes, she was the total package.
5. Claire Danes: Sophisticated, cute, BFFs with Winona Ryder, and super chic style too. To top it off, she got to make out with Leo DiCaprio and Jared Leto! Yes, she ruled the ’90s.
6. Drew Barrymore: No one had cooler style in the ’90s than Drew! She always had that chic thrift-store look, when — let’s be honest — she more than likely wasn’t wearing thrift-store clothes.
7. Mariah Carey: In the late ’90s she was all about short skirts, stilettos, and BIG HAIR. Also, let’s not forget she had Derek Jeter to accessorize her look with.
Jakob Dylan: OK, so maybe you didn’t want his style, but you did want to stare into his blue eyes while he sang “One Headlight” to you on his acoustic guitar.
BONUS: All these oh-so-pretty-then hairdos.
But really, how many different hairstyles is Sarah Jessica Parker rocking in this photo?
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