SJP
This is from the June 2, 1998, screening of the first episode. And nothing says "student work" in Tim Gunn's voice quite like this outfit, where a potentially reasonable dress that DEFINITELY matches someone's mother's wedding china has been defaced with a bodice AND a square from a potato sack. Also please note the presence of -- I think -- one of those metal headbands with prongs, which sort of marries the concept with a banana clip. Because I think there's another one at play in this slideshow, too.
Kim Cattrall
There are other shots of Kim from this event where her dress did not seem to be slipping as much, so clearly it was a nuisance. I would say this is a very Samantha thing to have happen, but it isn't, really -- it's more of a Charlotte or a Carrie. If it were Samantha, and it were slipping, she'd most likely be like, "Oh, FUCK IT," and yank it all the way down and then keep modeling the whole way through.
Kristin Davis
This is all stuff she could wear again today.
Cynthia Nixon
I have no idea what the rest of Cynthia's outfit was, because apparently the photographer was too taken with her exorbitantly 90s hair to bother. I THINK this is based on a similar type of headband as SJP's? But also potentially based on Donna Martin, or Clare Arnold, or even Kelly Taylor, all of whom had really terrible hair days on Beverly Hills, 90210, around this time. It's just... it really is symbolic of how the show itself botched Miranda's hair. They never knew what to do with it. I always thought Cynthia was being forced to act through some real sabotage.
It just never gets any less startling.
SATC
This is a promo poster dated 1999. Samantha's shoes are back in, although I wish they weren't. This whole thing is hilarious: The clothes really do NOT reflect any of what happened on-screen in season two and beyond, and it feels like Cynthia Nixon was directed to start a conga line and that enthusiasm for this notion waned dramatically and then died with Kim.
This is from season 3, at which point they went bonkers with a wind cannon.
This is from the same season, same outfits. For some reason they told SJP to sit like an entitled dude on the subway. And Kristin Davis looks miserable, for some reason? Kim Cattrall seems OVER IT and more than happy to be stashed in the back.