Chit Chat: The Best & Worst Oscar Fashion Ever!

Worst:

Matthew: One of my picks for worst is Celine Dion at the 1999 Oscars.

Marg: I second this. Celine shouldn’t try to be edgy, and this is proof of that.
Matthew: She looks like a 4 year old that tried to dress herself but missed one step. Still though, she is proud of her accomplishment. 

Marg: My first choice for worst goes to Gwyneth Paltrow in 2002. She looked dead. And really was just flapping in the breeze breast-wise. 

Matthew: Even celebrities need bras Gwyneth.

Marg: The sheer top did her no favours, either. That woman needs vibrant colour.
Matthew: You can't have a worst dresses Oscar list without Whoopi! 1993 & 2009!

Marg: The colours! The pants! 1993’s opened like a curtain, it was a treat for the eyes!

Matthew: I don’t mind the silhouette. Whoopi can pull off weird things. It’s the damn color combo... fugly.
Marg: 2009’s was lacking in the silhouette department. Looked like a leopard print maternity dress.
Matthew: Horrible.

Marg: One of my all-time favourites for worst dressed was Barbra Streisand in 1969... It was sheer, you can see her bum (an Oscars no-no!), and there were bell-bottoms.
Matthew: I think that outfit would have looked really awesome as a costume in La Cage Aux Follies.

Marg: I had to google that. You’re right.
Matthew: My final pick for worst dressed is Uma Thurman in 2004. Normally when you see her she is really classy and refined. I don’t think that she was staying true to herself.
Marg: I wonder if she did that purposefully - just wanted to do something totally out of the box for her, and it backfired.
Matthew: Plus she looked like she just tied a sash around her bedding and called it a night.

Marg: Jennifer Connolly, 2002
Matthew: The Oscars are held in L.A right? That would imply that it’s warm. Therefore no scarf Jennifer. No scarf.
Marg: She looks like a used coffee filter.

Gallery of our Worst Oscar Fashion

Best:

Matthew: Meryl Streep 2010 is one of the more recent fav looks of mine. I thought she looks hot, classy and elegant.

Marg: Ah yes, the white! Very sophisticated! 

Matthew: And here is a fun fact: It was designed by Chris March, a Project Runway alum who didn’t even make it to fashion week. He also designed her Golden Globes dress that year. 

Marg: That is a fun fact!

Matthew: Love me some fun facts!

Marg: Marion Cotlillard, 2008. She looked like a winter mermaid! In a good way.

Matthew: She accessorised very nicely.

Marg: It looked fun to wear too. I’d make swimming noises. 

Matthew: It would have been funny if it made the same noise that splash pants make when she walked. 

Matthew: Diane Keaton 1978. Back in the days when there were no stylist to do the work for you. Whatever you wore was your creation. 

Marg: Wow. She is really the only one who could pull that off. I dig it. My next pick goes to Elizabeth Taylor in 1960 - gorgeous! 

Matthew: That was going to be one of my picks! What a looker. 

Marg: My love for that woman knows no bounds. And the colours of the dress! Totally wasted on black and white film. 

Matthew: I wouldn’t mind if gloves came back. Okay, Grace Kelly 1956. A fashion icon and for good reason. She looked classic, effortless and beautiful. 

Marg: Oh my god, yes. Perfection. I like her gloves too! They do need to come back! Audrey Heburn, 1954. It is actually pretty much my dream wedding dress. 

Matthew: Another classic! I could go on with this forever! Shirley MacLaine 1975! Michelle Williams 2006! Kate Hudson 2003! Lauren Hutton 1975! oh it goes on and on and on. 

Marg: I like a lot more of the gowns from the 1950s and 60s - none of those women were going braless to the damn oscars, that’s for one thing!

Matthew: Okay- so do you have any overall favorite celebrities? Someone who consistently brings it every time they show up. 

Marg: Helen Mirren. She looks better than most of the 25 year olds. 

Matthew: Nicole Kidman always makes interesting choices. Some are hits, some are misses, but you can tell that she wears whatever she wants. I admire that. Oh an Bjork. Balls of steel. 

Marg: On that same note, Tilda Swinton. I always want to know what she wore. Always. 

Matthew: And there you have it! Happy Oscar Sunday!!

Gallery of our Best Oscar Fashion