Jessica Stein loosens her style up and gains her confidence.
has the most influence in my wardrobe. It was a time in fashion when the ’90s minimalism was still prevalent, but there were glimpses of what was to come in the excessive Noughties, like sassy pops of colour and riled-up prints. I always call it, “minimalist with a side of sauce”. Nothing feels try-hard; nothing feels over-the-top. The film perfectly encapsulates this era.
As the title suggests, the movie focuses on Jessica Stein, played by Jennifer Westfeldt. The Wikipedia description sums her up, “Twenty-eight-year-old Jessica Stein is an attractive, Jewish, neurotic copy editor at a small fictional New York City newspaper.” That’s about right. Stein is a Long Island transplant and a stickler for punctuation. At the beginning of the film, we see she has a string of bad dates, for which she wears knee-length slip skirts and a rotation of cardigans.
Enter Helen Cooper, played by Heather Juergensen. Cooper is the archetype of a downtown New York knockout: killer clothes, job at a trendy art gallery, roster of men who think about her, and not the other way around. One of the first scenes with Cooper opens with her entertaining three vastly different suitors at a gallery party and then hooking up with the bike messenger in the back room. She’s dressed in peel-them-off leather pants and an itty-bitty, custom-made cinched blazer.
Take their first date. Cooper is sitting at the bar in a semi-sheer fuchsia top – could it be Gucci? – with a thin matching scarf strung around her neck, super-tight jeans, and stiletto boots. Stein, on the other hand, looks like she’s come out of a Nine West catalog in a stiff grey dress and a cream cardigan. After a few drinks, Stein loosens up and so does her wardrobe: her cardigan ever-so-slightly slips off to reveal her dress strap.
By the end of the film, we see that Stein has found herself. Her hair is now wavy and she’s walking down the street in a denim jacket and a floral slip dress to meet Cooper, who is wearing almost the same thing. She’s become a different person thanks to Cooper, proving it’s as much of a love story as it is about clothes.
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