Yesterday we featured the timeless, the ethereal and the downright swoon-worthy Academy Award looks from 1975 on. Today, we’re doing a 180 and bringing you the worst (or most daring, depending on who you ask) Oscar dresses of the last 20 years. These are the looks you talked about, puzzled over and winced at–the “What were they thinking?!” ensembles that haunt top stars to this day!
It’s always easy to pick on the ’80s, the decade when all fashion bets were off, but that’s a little too easy–oh, sure we’ll include a few but there are plenty to choose from every decade. Read on to see our picks for the most sartorially challenged, who wore it worst and those who took Oscar a little too far.
Many critics have made a turn back time joke about Cher’s Bob Mackie look from the 1998 Oscars. We’ll refrain, if only because she is an inspiration to us–just know we were very, very tempted.
Before vampires were a red-carpet staple, and long before she was a glamorous A-List-Goodwill-Ambassador-mother-to-6-children and one half of the duo known as Brangelina there was: Angelina, Interrupted. Undeterred by her dress and creepy affection for her brother, the Academy awarded her an Oscar shortly after this picture was taken, and an international superstar was born.
Tilda Swinton exists in a time and space so far removed from our boring mortal existence that she can do no wrong. Sure this dress is included in every worst dressed list from Marie Claire to the Hollywood Reporter, but we kind of don’t care. We just added it in because it gave us yet another reason to fawn over her. Also, it’s Lanvin, 2008 and she looks comfortable *shrugs*.
Faith Hill can and does reign as a country queen (and one of music’s most beautiful women), but this shimmering rainbow number is better suited to a cereal box, where it’s sickly sweet appearance would go relatively unnoticed.
We admire Helena Bonham Carter’s dedication to a look–even if said look started in 1987. That is all.
When Whoopi Goldberg presented in 1993, she wowed the crowd in a shimmering, patterned number with matching shoes and all was almost right in the world–then she pulled back her skirt to reveal matchy-matchy pants and here we are.
It wouldn’t be the Academy Awards without someone taking Oscar literally. It doesn’t matter is you’re the esteemed Meryl Streep (in 2012, no less), the stunning Cate Blanchett (wearing Valentino, circa 2005) or Mid-nineties Lizzy Gardiner, wearing American Express–sometimes you have have to go for the gold. Do you have an Oscar look you love to hate? Leave it in the comments, below!
Photos via Getty Images.