My Picks For The 20 Fugliest Red Carpet Oscar Dresses Of All Time.

above: Sally Kirkland never fails to wear some sort of monstrosity to the Oscars

As I watch today’s Red Carpet for the 85th Oscars, I’ve decided I have to share with you the absolute most hideous dresses from the past – in no particular order. Several sites and blogs feature the ugliest dresses ever worn to the Oscars, but, as is typical, I disagree with many of them. So, I’ve decided to post my own pics of what I feel are the 20 most hideous frocks ever worn to the Academy Awards.

Ugliest Oscar Dresses Of All Time

View at your own risk.

Barbra Streisand:

Helena Bonham Carter:


Kim Basinger:

Demi Moore:

Celine Dion:


Faye Dunaway:

Geena Davis:

Lara Flynn Boyle:

Faith Hill:
faith hill

Gwyneth Paltrow:

Jennifer Connelly:

Kate Hudson:

Melanie Griffith:

Sophia Loren:

Uma Thurman:

Whoopie Goldberg:

Florence Welch:

Bonus: I initially didn’t include this because I don’t like mocking someone who is not around to defend herself, but Anna Nicole’s tight turquoise velour dress would be my 21st pick. It looks cheap – and more absorbent than a Bounty paper towel:
Anna Nicole Smith red carpet 2006

You don’t see many dresses this ugly anymore, especially on the likes of big celebs who, after making the worst-dressed list for that year, wised up and hired stylists. Demi Moore and Kim Basinger (both of whom designed the dresses you see them wearing here) never made as bad a fashion faux pas again.

During tonight’s Oscar’s broadcast, I’m expecting the ugliest visual offenses to be Botox injections and plastic surgery.

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