The year is 2002. We are post-9/11, but pre–most things we remember about the 2000s (The O.C., MySpace, etc.). Jennifer Lopez and Ben Affleck are an A-list couple who are not yet engaged for the first time. And perhaps because she does not need to match her ensemble to the pink diamond rock he will shortly present to her, Jenny From the Block rolls up to the MTV Video Music Awards wearing…this:
Reminder: Ally McBeal had just ended, the show that tricked people into thinking dressing like a lawyer was hot. Also, 2002 might be the least stylish year ever. Remember, kiddos, Y2K wasn’t all about low-rise jeans and letting your aquamarine bra straps poke out from beneath a white tank top. We were also putting frills and ruffles on every damn thing.
The shoes? Timeless. The skirt? Sexy! The jacket? Literally just rip the extra frills off and you have a perfectly good Victorian blazer thing happening. As for the curls—they should be pinned back into an Old Hollywood look, paired with a silk gown and worn to the Oscars, darling!
The makeup is lovely, and the handbag is cute.
Standing behind Lopez is future president Donald Trump, whose show The Apprentice wouldn’t premiere for another two years, so I’m not totally sure why he was at an MTV awards show, but such is Hollywood. I was genuinely too distracted by Lopez’s outfit to even notice him the first time I looked at these pictures.
For every Green Dress there’s a Weird Black Outfit. Much like in her relationship with Affleck, Jennifer Lopez learned from her past and did better the next time. But the internet never forgets.
Keep an eye out for Glamour‘s coverage of the 2022 VMAs, happening this Sunday, August 28, here.
