Happy Tuesday, dear readers! Each week, we’ll rank the top 10 films in a specific category. While we aim to tie these lists to big releases, that won’t always be the case. Our goal? For you to enjoy, share your own lists, and join in on a lively, friendly debate. This is an interactive space to build community here at The Contending.
No fancy intros, no long essays – just a category and a list. Sound good?
Last week, I ranked the ten greatest directors of all time in advance of the Directors Guild Awards. With Paul Thomas Anderson (One Battle After Another) predictably taking home their top honor (along with wins at the Golden Globes and Critics Choice Awards), the race for Best Director feels pretty locked in. Will Best Picture follow suit? That’s still up in the air, but historically, the DGA winner’s film has gone on to claim Best Picture at the Oscars most of the time (around 76% alignment).
This week, both the Costume Designer’s Guild (CDG) and Makeup and Hairstylists Guild (MUAH) will award their top prizes in their respective categories. Flip a coin, and we land on honoring the ten greatest costume designs of all time. This week you are in for a special treat, as The Contending’s top fashionista, Joey Moser, will be including his personal list as well.
Here’s my ranking of the Top 10 Greatest Costume Designs in Film History.

10. A Clockwork Orange (1971) Costume design by Milena Canonero

9. The Matrix (1999) – Costume design by Kym Barrett

8. Titanic (1997) – Costume design by Deborah Lynn Scott

7. Amadeus (1984) – Costume design by Theodor Pištěk

6. Cleopatra (1963) – Costume design by Irene Sharaff

5. Breakfast at Tiffany’s (1961) – Costume design by Hubert de Givenchy, Edith Head, Pauline Trigère, and Joan Joseff

4. Gone with the Wind (1939) – Costume design by Walter Plunkett

3. My Fair Lady (1964) – Costume design by Cecil Beaton and Michael Neuwirth

2. Star Wars (1977) – Costume design by John Mollo

1. The Wizard of Oz (1939) – Costume design by Adrian Adolph Greenburg
Here’s Joey’s list:
10. White Christmas (1954) – Costume design by Edith Head
9. Down With Love (2003) – Costume design by Daniel Orlandi
8. All About Eve (1950) – Costume design by Edith Head
7. Dick Tracy (1990) – Costume design by Milena Canonero
6. Titanic (1997) – Costume design by Deborah Lynn Scott
5. All That Jazz (1979) – Costume design by Albert Wolsky
4. My Fair Lady (1964) – Costume design by Cecil Beaton and Michael Neuwirth
3. The Fall (2006) – Costume design by Eiko Ishioka
2. The Cell (2000) – Costume design by Eiko Ishioka and April Napier
1. Bram Stoker’s Dracula (1992) – Costume design by Eiko Ishioka
What do you agree/disagree with? What film has the greatest costumes?








Thanks for the double list.
Also thanks for making me look up late Ms Eiko Ishioka and her exceptional works. Not the biggest fan of Bram Stoker's Dracula (1992) but her divine costumes in Mr Singh's The Cell and The Fall are another story..