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Best Dressed Women In Film | Top Ten Nominees

We all adore Hollywood and even more so the heavenly wardrobes that come with it. We romanticize the stories in the movies and the characters and although it probably sets us up to fail in adult life they have a profound effect on us, especially our personal style. Some of the most iconic roles played by women have gone down in history but today we are looking at those whose significance was due to their unquestionable style. From the androgynous aesthetics from Annie Hall to the 50’s High Society chic from Grace Kelly these are the roles that are unforgettable and have left their mark within the fashion world. And the nominees for Best Dressed Women in Film are;
  • Ginger McKenna, Casino - Sharon stone 
  • Penny Lane, Almost Famous - Kate Hudson 
  • Vivian Ward, Pretty Woman - Julia Roberts 
  • Tracy Lord, High Society - Grace Kelly 
  • Annie Hall, Annie Hall - Diane Keaton
  • Jenny Cavilleri, Love Story - Ali MacGraw
  • Cecilia Tallis, Atonement - Kiera Knightley 
  • Nina Sayers, Black Swan - Natalie Portman 
  • Penelope Lannier, A Bigger Splash - Dakota Johnson 
  • Emma Recchi , I am Love - Tilda Swinton

#1 Ginger McKenna, Casino - Sharon stone 

Outfits from the film Casino Ginger Mckenna is the wife to Sam ‘Ace’ Rothstein in the iconic crime film Casino set in 70’s Las Vegas. Based on real people; Sam was inspired by Frank Rosenthal ‘Lefty’ who ran several casinos and his wife Geri who was an American socialite, model and showgirl. The couple were both known for their involvement in criminal activity. The styling throughout is the making of both characters, it is everything you want from 70’s new money American hustlers. Ginger is the ultimate glamour puss in her sequin evening gowns and fur shawls. 

#2 Penny Lane, Almost Famous - Kate Hudson 

Penny Lane in Almost Famous Almost Famous is a semi-autobiographical film based on the producer, Cameron Crowe’s experience as a young teenage writer at Rolling Stone magazine. In the film, Penny Lane is based on Penny Thrumbull who formed the groupie in the girl band ‘The Flying Garter Girls’ in the 70's. Each band member had their own nickname and became well known for travelling the country with numerous rock bands. In the film you can’t help but fall for Penny Lane, kind-hearted and wild her wardrobe is the ultimate luxe boho, effortlessly cool, 70’s hippie, rock and roll vibe. 

#3 Vivian Ward, Pretty Woman - Julia Roberts 

Vivian Ward in Pretty Women Vivian Ward is a hard-on luck prostitute who spends the night with multi-millionaire Edward Lewis after meeting on Hollywood Boulevard. The story is a modern-day Cinderella and after hiring her for the week they fall in love, however, that is arguably the second-best bit about the film. The first is how effortlessly she pulls off, street corner edge to high style polka dots at polo matches. Her wardrobe throughout is nothing but iconic. 

#4 Tracy Samantha Lord, High Society - Grace Kelly  

Grace Kelly's Outfits in High SocietyHigh Society's Tracy Samantha Lord has the pick of three very different men. Played by Grace Kelly she is due to remarry however her ex-husband is still in love with her and to complicate things further the wedding photographer played by Frank Sinatra falls for her too. We can see why though, it doesn’t get much dreamier than those vintage, demure Hollywood dresses she so elegantly pulls off, complete with clipped curls and white gloves. 

#5 Annie Hall, Annie Hall - Diane Keaton

Annie Hall Oufits Annie Hall is the 1977 American romantic comedy directed by Woody Allen. Allen plays Singer Alvy who tries to figure out why his relationship with the eponymous female lead, played by Diane Keaton doesn’t work out. In the role specially written for her, Annie’s style was Diane’s style in short! Classic, eclectic oversized jackets and waistcoats Annie Hall became a household name within the fashion world. 

#6 Jenny Cavilleri, Love Story - Ali MacGraw

Jenny Cavilleri in Love Story Love Story is the original American romance with privileged Harvard Law student Oliver Barrett IV falling in love with middle-class girl Jenny Cavilleri to the dislike of his parents. Her character stole the hearts of thousands and her outfits have stood the test of time, providing the manual on the pinical Autumn Winter wardrobe. From classic high neck knitwears to camel coats, she sculpted our sophisticated essential everyday looks. 

#7 Cecilia Tallis, Atonement - Kiera Knightley 

Kiera Knightly in Atonement Atonement is a love story of a young couple whose relationship becomes impossible when boyfriend, Robbie Turner, is falsely accused of sexual assault. In the sad story Cecilia’s wardrobe full of silk, lace delicate cuts, highlights the middle-class luxury of pre-war England. Her scene in the green silk, floor-length gown is still unrivalled in the cinematic world cementing her amongst the best dressed women in film. 

#8 Nina Sayers, The Black Swan - Natalie Portman 

Natalie Portman in the Black Swan The psychological horror The Black Swan delves into the constant pressures for perfection dancers face. Deranged ballerina played by Natalie Portman becomes obsessed with the new girl’s more free-spirited style and attitude. The film generated a lot of hype as fashion-industry favourites Kate and Laura Mulleavy from Rodarte designed seven of the ballet outfits. Controversially they were not eligible for an Oscar for best-dressed costume.

#9 Penelope Lannier, A Bigger Splash - Dakota Johnson 

Dakota Johnson in A Bigger Splash Set on the beautiful Italian island of Pantelleria, Tilda Swinton plays a rockstar holidaying with her boyfriend. When she bumps into her previous lover with his supposedly 22-year-old daughter things take a turn. The daughter Penelope Lannier played by Dakota Johnson stands out for her perfectly selected summer pieces and trendsetter sunglasses.

#10 Emma Recchi, I am Love - Tilda Swinton 

Tilda Swindon in I am Love In another Luca Guadagnino’s film, Tilda Swinton plays the part of a cheating wife who falls in love with a young chef. In the dramatic family storyline, the wealthy wife of second-generation textile manufacturers is everything you want from exalted Milan society. Dressed in awe-inspiring, chic minimalist dresses, Raf Simons for Jil Sanders was responsible for her impeccable outfits predominantly picked from the AW 2008 shows. 


Best Dressed Men In Film | Top Ten Nominees

Take a look at our top 10 nominees for Best Dressed Men in Film - The ones whose iconic style catapulted them into the hall of fame.

Holly Thompson
Holly Thompson Writer and expert

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