10 Charlotte York Outfits That Will Remain Stylish in 2025

Because we’re doing this chronologically, Charlotte York’s fashion starts very traditional, even a bit boring. In Season 1, Episode 4, Charlotte wore a business casual look consisting of a dark-colored pencil skirt and a long-sleeved blouse while weighing the pros and cons of all things anal sex. In 1998, even the mention of beginner butt play was extremely taboo, so to have this all play out while Charlotte “I don’t want to be the up-the-butt girl […] Men don’t marry up-the-butt girl” York, is wearing her timeless, business casual look, fans get a fashion moment they’ll never forget.

The Charlotte York we were introduced to in Season 1, Episode 4 may not have wanted to be Mrs. Up-The-Butt, but by Episode 8 of the same season, she was looking into exploring threesomes, or at the very least some version of polyamory and open relationships. And, she did so in a matching pink tweed suit that may or may not have been Chanel. (Honestly, since it was the first season, it was probably a dupe.) Either way, this is a look that’s just as easily on-trend in 2025 as it was in 1998.

Charlotte’s gallery looks were definitely some of her finest, and this grey plaid dress with the artfully designed collar and black belt is no exception — probably because it’s by Thierry Mugler, a man who knew his way around a bolt of fabric. What’s so great about this dress is that, as sophisticated as it is, it still offers quite a lot of chicness, thanks to being off-center and adorned with beautiful silver rectangular buttons. Anyone could easily pull this off today, and no one would know it was designed 26 years ago.

When the ladies showed up to a tantric workshop in Season 2, Episode 16, Charlotte was wearking a look so classic, so never-going-out-of-style that if you haven’t worn this outfit yourself, you’ve walked past dozens of people this week alone wearing it: khaki pants, white button-down oxford shirt, and loafers. If you were ever going to curate a closet of anti-trend staples that will always be in style, these three items would be on the list. It’s worth noting that only Charlotte took the tantric class seriously, meaning she’s probably the only one who learned that sex is about the journey, not just the destination.

Here it is: the iconic Prada lipstick skirt. When asked by Grazia in June 2023 about her favorite of Charlotte’s outfits, Kristin Davis didn’t hesitate when saying, “Listen, this is something people ask us all the time! I just say lipstick skirt.” The skirt was so beloved that it was worn twice in Season 3 (Episodes 4 and 7), and because Davis adored it so much, she took it home, and it now resides in her closet waiting for a special occasion. That bit of pop culture trivia aside, the skirt was then, and will always be, iconic, something that was amplified by keeping the top a simple, yet elegant choice: a classic white button-down Oxford shirt.

Having fallen in front of Trey MacDougal’s cab in Season 3, Episode 7 — in her Prada lipstick skirt no less — by Episode 9, Charlotte and Trey were officially in love, and fashionably compatible. In this particular scene, where the two of them are standing outside Tiffany and Co., looking into the store, Charlotte is wearing another dress by Thierry Mugler. Similar to the other Mugler look from Season 2, Episode 6, this halter dress, with its plunging bow front, has a standout collar and clean, crisp lines, although the skirt on this dress is A-line, as opposed to pencil in its cut. It may have been 2000 when Charlotte said, “alrighty!” to stopping at Tiffany’s for a ring, but this dress is perfect for any afternoon event in 2025 — especially proposals done on 5^th Avenue.

Leave it to Charlotte to perfectly nail a look for an afternoon of playing tennis. While Charlotte doesn’t actually play any tennis in this adorable white collared dress with pintucks across the bust and pleats in the front of the skirt, she does have a pretty hot and steamy make-out session with the gardener. In 2025, this dress still works for tennis and, of course, any extra-marital kisses you might have in mind. Although having to tell your partner you were unfaithful is never an easy road to navigate, no matter how flirtatious a dress like this makes you feel, you may want to stick to just fantasizing about such things.

Like a lot of the dresses Charlotte wore during her marriage to Trey, this is another timeless beauty. The white dress covered in red poppies and pulled in at the waist with a thin black belt is both sophisticated and fun, as well as on-trend from anytime between the 1940s and now. This means investing in a dress of this cut and style is a good idea, because you’ll probably be able to wear it for the rest of your life and forever be en vogue. Unless, of course, people really do start wearing intergalactic spacesuits, as has been the assumption about the 2000s forever. As always, Charlotte pulls off her single strand of pearls without looking stuffy, but with pure elegance.

Just 10 episodes later, Charlotte found herself seriously thinking about repurposing her 2.17-carat, platinum setting engagement ring from Tiffany and Co. for another piece of jewelry made with the same diamond. Although her marriage to Trey didn’t last, as far as timeless fashion goes, Charlotte continued to flourish in a beautiful blue and white plaid strapless dress by Moschino. In true Charlotte style, the dress even had a keyhole and bow across the top. In 2002, it was the perfect summer dress to wear while flirting with turning an engagement ring into a necklace, and in 2025, it’s easily the best dress for brunch that someone can have in their closet.

After suffering a miscarriage and finding strength while watching a documentary about Elizabeth Taylor, Charlotte pulls herself from the couch to attend Brady’s first birthday party. In iconic fashion, Charlotte puts on a pink strapless Eric Way dress with a sweetheart neckline and a thin black belt (with a bow!) around the waist. She’s carrying a small white bag, her hair is up, and it’s all very much an ode to Elizabeth Taylor, as she struts down the street wearing black heels and sunglasses. The style and the color of the dress speak to the fact that sometimes what you wear can take your mental and emotional health in a completely different direction. It’s also a timeless choice that can be worn in any decade and to any event — even a toddler’s birthday party.