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"Anytime she puts that rag on her head, I kind of hold my breath," Rubenstein said. And the Hermes scarf Carrie paired with a pink vintage prom dress is no exception. "This is TV, not fashion," he explained. Weinberg seconded his opinion: "This looks like something Katy Perry would wear to the Grammys," she said. "And those white Manolo pumps were like a Catholic-schoolgirl-gone-bad." (Photo: Diane L. Cohen/Getty Images) More of Carrie's Craziest Looks
"That's what Pat would call an 'around the way' look," Weinberg said of Carrie's kooky combination of tie-dye leggings, a bright blue kerchief, and a wildly-patterned Chanel blouse. "She looks like a girl from the Bronx, or Brooklyn." Rubenstein seemed equally amused by the outfit, although he disagreed about the provenance: "This is Carrie in cartoon land! But does it make me laugh? Of course." Darman, for his part, is still a fan. "This look still has edge," he said, "and lots of MTV appeal." (Photo: BILL DAVILA/ Retna) More of Carrie's Craziest Looks
The colorful patchwork coat that Carrie wore to stalk Aidan after Stanford spotted him in the Sunday Times in Season 3 was, Weinberg reported, actually one of Field's personal pieces. "We just threw this together," she said of the outfit. "It was one of those moments we didn't plan out." Rubenstein guessed as much. "This look is more Pat than Carrie," he said. "Pat was a pioneer downtown designer, and the streak of downtown club girl that runs through Carrie's wardrobe comes from Pat Field." (Photo: HBO / Courtesy: Everett Collection) More of Carrie's Craziest Looks
Carrie and Samantha's coordinated sailor styles put both Field and Weinberg in mind of a classic 1960's girl group. "It's like they're the Supremes," Field said. Seaworthy though their outfits may be, Rubenstein doesn't recommend that fashionistas follow suit. "I don't think anyone should dress like this," he said. But Daman once again defended Carrie's choice (and, indirectly his own—Weinberg reported that he picked these clothes.)"Nobody sails through fashion like Carrie! She keeps the nautical trend cool, contemporary, and casually chic." (Photo: HBO / Courtesy: Everett Collection) More of Carrie's Craziest Looks
Once again, Carrie went costume-y in a cropped, striped vintage suit. "This is very Joe DiMaggio, 1939," Weinberg says of the season four ensemble. "The pinstripes are okay; the newsboy hat was very much my look at the time." (Photo: Bill Davila / Retna) More of Carrie's Craziest Looks
Carrie was often ahead of her time: While this Claude Pierlot one-piece struck many fans as being a little too bare when Carrie wore it to the farmer's market in season 4, Daman was quick to point out that "Rompers are currently one of the biggest trends going, and Carrie was one of the first to openly embrace them." Fair enough, but we still think that pairing one with peek-a-boo heels is a little too much. (Photo: HBO / Courtesy: Everett Collection) More of Carrie's Craziest Looks
"Anytime she puts that rag on her head, I kind of hold my breath," Rubenstein said. And the Hermes scarf Carrie paired with a pink vintage prom dress is no exception. "This is TV, not fashion," he explained. Weinberg seconded his opinion: "This looks like something Katy Perry would wear to the Grammys," she said. "And those white Manolo pumps were like a Catholic-schoolgirl-gone-bad." (Photo: Diane L. Cohen/Getty Images) More of Carrie's Craziest Looks
"This is not one of my shining moments," Weinberg admitted. Peek-a-boo lace underthings were a Carrie staple, but the look, seen here in season 5, didn't always work. "I have a problem with the cropped pants and the major bra," Rubenstein said. Nor did he welcome the return of the dreaded do-rag. "She looks like she should be cleaning my apartment." (Photo: Bill Davila/WireImage) More of Carrie's Craziest Looks
