Penelope Wilhern – Penelope (2006)
Designed by: Jill Taylor
Penelope may be a film focused on the importance of inner beauty, but wardrobe designer Jill Taylor did a great job of giving the title character, Penelope Wilhern, a fantastic sense of style in addition to her smarts and wit. Her wardrobe is very ladylike, sometimes bordering on whimsical. She has a beautiful collection of jewel-toned coats, a trademark vibrantly patterned scarf and even sports a beautiful wedding gown with a jeweled bodice. I would describe her wardrobe as very classic, but with  unique details (such as the red piping seen on the coat above) that reflect her character’s zest.

The Women

Sylvia – The Women (1939)
Designed by: Adrian
I know what you’re thinking – another Roz Russell character? It may seem as though she appears on this list one too many times, but the fact is, her films had phenomenal wardrobes. And in a film like The Women, with its entirely female cast and slew of glamorous outfits, she still stands out. Her wardrobe is so varied. Sometimes structured, sometimes draped, sometimes fluffy, the only consistent thing about her wardrobe is that the outfits are always over-the-top in the best way. The dresses on their own are gorgeous, but her accessories are what really takes the cake, namely those crazy hats that are a trademark of Sylvia. Even the dresses themselves feature entirely quirky details, such as the dress pictured above, which has eyes prominently displayed on the front.

Claire Huddesen – On the Town (1949)
Designed by: Helen Rose
Claire may not wear quite as many outfits as we see some of the other ladies in this series wear, but the old adage is true in her case: quality over quantity. Her dresses come in very vibrant shades, notably hot pink and a stunning, deep green. (In the video above, Ann Miller as Claire shows off a lovely green dress with plaid accents in one of the film’s best musical numbers.) Claire’s goal is to find her “prehistoric man,” but there is absolutely nothing prehistoric about her sleek wardrobe, designed in perfect late-1940s style. Her trademark swingy skirts are perfect for carrying out the film’s many fun dance numbers, looking polished and pretty all the while.

Pretty in Pink

Andie Walsh – Pretty in Pink (1986)
Designed by: Marilyn Vance
As the title of the film suggests, pink is definitely Andie’s color, and she wears a whole lot of it in the film – usually in very flattering, aesthetically pleasing pale shades. But she doesn’t only limit herself to one color. Plethora of pink aside, Andie’s wardrobe is quintessential ’80s cool. Her pieces are a bit funky and always accompanied by bold accessories, giving her a quirky and unique vibe. She definitely stands out against the crisp, preppy styles of the “richies” that populate her school.