Celebrities’ worst fashion mistakes

Many celebrities and fashionistas attend runway shows at New York Fashion Week, but even the most fabulous women make style missteps from time to time. We hit the tents and asked every star we could speak with the same question: “What was your worst fashion moment ever?” Some celebs were reluctant to answer, but many laughed and happily shared their past outfit disasters. Here are their honest and hilarious answers along with many of the horrible looks in question—yes, we tried our best to track them all down. Sorry, ladies!

Sofia Coppola, director

“Oh yeah. Yeah, of course. Everyone does [have fashion regrets]. I don’t really want to describe it for you, but I’ve had my moments.”

Julia Stiles

“Oh, I have so many fashion regrets, but we don’t need to dwell on those. I try to move on from those. Probably all of college was a big fashion regret. I just think I hadn’t quite grown up yet, and I dressed a little too sloppy.”

Lo Bosworth, former star of MTV’s “The Hills”

 “Trucker hats! [Laughs] I wore them in high school.”

Ashanti, singer

 

“It was for one of my first appearances on MTV. It was a leather corset and it had, like, these strings dangling down, but on camera it looked like I had a hairy stomach. I really didn’t like that."

Ramona Singer, star of “The Real Housewives of New York City”

“I had boots like these these but they were very fitted, but they were like, fake snake. And like, what was I thinking? They were poly snake boots. They were like a python look. At the time I thought they were cool, but looking back a season later, I’m like, ‘what, was I crazy?’”

Kellie Pickler, singer and former “American Idol” contestant

 “My mullet! I used to have a mullet. Yeah, that wasn’t pretty.”

Rose McGowan

“Well, I have worn some things that don’t square with my personality, because my family nickname is Miss Priss. I’ve tried a couple things that aren’t so prissy, which is odd for me.”

Jill Zarin

“A Gucci top for one of my interviews on ‘The Real Housewives.’ I look like my grandma... on not a good day. It just made me look very top heavy, and that’s when I decided to get my boobs reduced. I looked horrible.”

June Ambrose, celebrity stylist

“Recently I had on a pantsuit and photographers on the red carpet don’t tend to shoot you from the angle you want, and I looked like I was four feet tall. But in the past, back in the day: a pink cow print Fendi coat.”

Jennifer Love Hewitt

“It’s very easy. I wore nude suede pants, and a corset that was short with my stomach showing to “The Beach” premiere. Why I did that I have no idea. And I crimped my hair with it on top of it. It was absolutely horrible. I’m surprised they didn’t kick me out of the business.”

Kelly Osbourne, singer/model/tv host and daughter of Ozzy and Sharon Osbourne

“Probably what I wore to the Clive Davis party a few years ago, because I had this wig on, and I looked terrible.”

Eva Amurri, actress and daughter Susan Sarandon

“When I was in middle school, I wore a lot of cropped tops during the Britney Spears era, and that’s probably not the best look for a 12-year-old.”

Keri Hilson, singer

“It’s probably not too far in the past. That always happens. I didn’t love what I wore on VH1 Divas. Not the threesome performance with Jennifer [Nettles], and Katy [Perry], not that. But what I wore for my solo performance, I didn’t love it. It’s all about flattering, and it looked like I had a diaper on. When I saw photos then I really knew how bad it was.” (Said "diaper" outfit pictured right.)

Michelle Tractenberg

“I wore a head-to-toe leopard ensemble for one of the “Charlie’s Angels” premieres, but I was 15 so I think that was OK. And then to a “Toy Story” premiere I wore a crushed velvet olive green head-to-toe catsuit with, like, spiders on it and faux fur sleeves. That was a classic, yeah, I need to bring that back into style.”

Linda Gray

“There’s a picture of the whole cast in front of Southfork [Ranch] and a wardrobe lady said, ‘Oh here, just put this on’ and I said, ‘But it feels like a dish rag!’ It felt like a dish cloth. [Ed: note Gray's yellow top, above right.] And she said, ‘Oh no. Nobody’s ever gonna see this picture.” It’s famous. And every time I look at that picture and I have to sign it, I cringe, and I think, I will never put something on just because they think it’s right... And of course there were all the shoulder pads in the ‘80s. They were so big I couldn’t get in the door!”

Kristi Yamaguchi, champion Olympic figure skater

“Oh yeah, a lot! A lot of skating costumes. Olympic year, which was ‘92 so you have to remember it was early ‘90s, I wore this lame costume that was red, white, and blue, and it was really kind of atrocious, looking back. [Laughs] With the ‘90s mall hair.”

Gabrielle Union

“Oh god. Probably what I wore to the “Bring it On” premiere a thousand years ago.”