Demi Moore’s look in Now and Then perplexes me, fascinates me, and ignites me. The 1995 film focuses on a group of four friends from the ’70s who go on coming-of-age adventures, which range from solving an age-old fictional murder to kissing boys, and the women they grew up to be 20 years later. The young versions of these women are a destined-for-showbiz “Teeny” (Thora Birch); a rebellious Roberta (Christina Ricci); a naive Chrissy (Ashleigh Aston Moore); and an imaginative Samantha (Gaby Hoffman). Fast-forward, and Roberta is now an obstetrician played by a deadpan Rosie O’Donnell; Teeny is a limo-riding TV host played by Melanie Griffith; Chrissy, pregnant and ready-to-pop, is played by Rita Wilson; and Samantha is now Moore, who has grown into a Marlboro-Red-chain-smoking sci-fi author with obviously a penchant for outré suiting.
Samantha fits the oddball, creative, career-driven archetype and certainly dresses the part. While Roberta wears a denim top, her glamour gal pal Teeny wears a cream skirt suit, and Chrissy is decked out in florals, Samantha arrives at this reunion in a three-piece suit. Yes, she wore a baggy, pinstriped suit to hang out at a quaint, American-dream house. There’s a striped top with an oversized collar, a chunky black tie, a burgundy knit sweater vest, and then the oversized blazer and pants. The whole look reminds me of the feeling when you have a multivitamin stuck in the back of your throat: It’s suffocatingly buttoned-up.
In case that wasn’t enough on its own, it’s all finished off with a tiny pair of tinted circular sunglasses—the size of multivitamins themselves—and a pair of black and white brogues that give me major Charlie Chaplin vibes. Her hair is done up in a braid crown like the former prime minister of Ukraine, Yulia Tymoshenko, and she arrives at a pregnant friend’s door with a cigarette in her mouth. I can imagine the writer’s room coming up with Samantha’s grown-up look. “She’s a weird writer. What do writers wear? Let’s put her in a big ol’ three-piece suit and give her a cigarette.”
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