Carrie's Best Looks Ever (part 2 - The Craziest)

The "Around the Way" Look

"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." Daman, for his part, is still a fan. "This look still has edge," he said, "and lots of MTV appeal."

Pat’s Patchwork Coat

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."

Carrie's Not-So-Classic Nautical

Carrie and Samantha's coordinated sailor styles put both Field and Weinberg in mind of a classic 1960s girl group. "It's like they're the Supremes," Field said. Daman, too, looked fondly back at Carrie's "cool, contemporary, and casually chic" take on the nautical trend. "I love it for TV," Rubenstein said, but that doesn't mean he thinks that aspiring fashionistas should follow suit. "I don't think anyone should dress like this."

Carrie’s Vintage Striped Suit

Carrie's cropped, striped vintage suit is "very Joe DiMaggio, 1939," according to Weinberg. And it turns out that the inspiration for at least part of this season 4 ensemble was Weinberg herself."The newsboy hat was very much my look at the time."

The "Running Errands" Romper

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."

The Do-Rag/Prom Dress Combo

"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."

The Visible Bra Look

"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. "It's so much cuter," he advised, "to show a little hair above the forehead. Then it looks like you're wearing a scarf."