Taylor Swift
This look feels pretty iconic at this point, but only because she was wearing it during The Interruption. Having said that: It IS a great dress, and her lipstick is perfect here. If you're going to be part of arguably THE iconic VMAs moment, at least you can rest easy knowing you weren't wearing a meat dress. (That was the next year.)
Kanye and Amber Rose
We were in New York for Fashion Week in 2009 -- a GREAT year for Fashion Week Front Row Coverage, truly; RIP NYFW front row coverage -- and I clearly remember looking up from my laptop during this red carpet and thinking, "is Kanye drunk?" He was. (I also thought this was the year that Heather interviewed him, but that was ALSO 2010, although he talked about the VMAs in that interview, which was great)
Beyonce
Beyonce was so far ahead of the High Fashion Fanny Pack trend. (I made a fanny pack joke about this look ten years ago, too. I'm nothing if not repetitive.)
Jennifer Lopez
Ah, yes! J Lo's dress that must have been very uncomfortable on her neck any time she moved her arms.
Lady Gaga
I totally forgot that Lady Gaga went through this The Birds period!
Gaga and Eminem
This was also very subtle and low-key, as one might expect from Gaga. Eminem looks SO CONCERNED here, like he's REALLY worried that Gaga cannot see well enough to walk in that headpiece.
Lady Gaga
"I haven't seen hardly any of this show, to be honest." (Yes, that's Perez Hilton behind her. 2009!!!!!)
Madonna
MEANWHILE, Madonna was in her Lady of the Manor phase (which I rather wish she'd return to, frankly). Facially, she looks AMAZING here.
Katy Perry
This has to be by The Blonds, and Katy looks fantastic in it. I believe she is a natural blonde, and she's blonde right now, but she looks so much more striking with dark hair to me.
Solange
This is so low-key for Solange!
Whitney Port
Weirdly, this dress has aged fairly well. She could wear it today.
Amanda Bynes
Well, this is basic AF, but La Bynes also looks great here (if super spray-tanned, but everyone was spray-tanned in 2009). I miss her.
Lo Bosworth
This also feels VERY much like something she could wear to the office today, with more daytome hair/makeup/shoes.
Stephanie Pratt
This was very Vegas, even then.
Lauren Conrad
She needs lipstick, but I also still like this dress, and I think you could ALSO re-wear this with the right styling. (It's a little short for 2019.
Leighton Meester
This dress is ALSO still cute, and those shoes are also still awful to me.
Alicia Keys
2009: Everyone wore really reasonable little dresses to this thing, that I hope they kept because they could wear them with different shoes and a moto jacket right now and it wouldn't be mega fashion-forward but literally no one would bat an eye.
Ashley Greene
But this feels VERY Homecoming Dance Class of 2009!!!!
Olivia Palermo
This is ALSO totally wearable right now, cold shoulders and all.
Amerie
Amerie may literally be wearing this with sneakers to pick up some fresh stone fruit at the farmer's market right now.
Cassie
Cassie might have too many bracelets. Even for 2009, when I was EXTREMELY attached to The Bracelet. (I still, of course, love a bracelet.)
Rose Byrne
Speaking of bracelet technology! This is cute, though, the kind of party dress you look back at, ten years down the line, and sigh, "I loved that dress."
Adrienne Bailon
Those boots ever worked with this dress.
Pink
This was REALLY the quintessential VMAs look for the aughts.
Gerard Butler
I'm fairly sure he's wearing this right now.
