Why does Carrie Bradshaw’s unconventional personal style feel so relevant in 2025?

Season Three of HBO’s And Just Like That... premieres this week, and with it comes an undeniable onslaught of wacky dressing—as evidenced by the set photos that have already leaked. In the trailer alone, Charlotte’s pairing a Blair Waldorf-style red headband with coordinating gingham. Miranda’s going camp in a silver one-shoulder dress. Lisa sits by the pool in a shocking yellow visor and matching vest. And Carrie bucks subtlety at every turn—whether she’s in sheer Simone Rocha or a larger-than-life Maryam Keyhani hat.

Though the level of absurdity may have reached new heights, it’s not exactly novel, especially where Bradshaw is concerned. And her throughline of sartorial defiance ignited a fashion dialogue still relevant today—particularly on Substack.

The fictional New-York-City-based writer and fashion connoisseur, who first won us over with her charmingly unique ensembles on the original Sex and the City, is renowned for her affinity for the unexpected, though most of which is often styled with more down-to-earth, feminine pieces to temper the blasphemy. (Costume designer Patricia Field calls this “mix-and-match fashion” in her memoir Pat in the City: My Life of Fashion, Style and Breaking All the Rules.)

Season Four of the original series holds one of Brashaw’s wildest moments: a psychedelic Chanel blouse, turned backwards and cut at the neck, with knee-length tie-dye leggings and stilettos. Season Three showed a ruched and tiered pink ‘80s mini dress with an Hermès silk scarf tied around her forehead. The pinstripe navy suit complete with pedal pushers, which she then paired with a newsboy cap and white pumps? Hot pants, a trench, and heels? The belt worn around a bare stomach? (The three of which are also Season Four.) It’s all a bit wild, but pertinently so.

Last month, Leandra Medine Cohen, Substack queen and founder of the now defunct fashion-blog-turned-lifestyle-site ManRepeller, recreated the last look in a post about styling stale pieces with something a little weird to freshen them up—or “bridge” them. “A risk I’ve never taken,” she writes, “belt on exposed bare skin.” Medine Cohen turned a tissue turtleneck into a crop top by folding and knotting it, then added a full Nikki Chasin skirt with the band tucked in to make it low-rise. Between which, she wore a One/Of belt “that I pulled off its parent pencil skirt” on her bare stomach.

“I often refer back to season four and early season five when I'm going through something because those were seminal style moments for me in cultivating my own sense (of style),” says Medine, of the era in which most of the funkiest outfits fall. “I think those are probably the seasons that Patricia Field was most on fire.” She was inspired in her early teens to mimic Bradshaw and mix Walmart boxer shorts with a Juicy Couture blazer and rhinestone flats.

Her breed of self-expressive dressing, which she championed both on ManRepeller and, later, her Substack, seems to parallel Bradshaw’s. As Medine Cohen says, it’s about using style as a form of “creative rebellion.” At the centre of a Venn diagram between the two women, you’d see swimsuits as tops, exposed underwear, quirky headwear, jewellery, jewellery, and some more jewellery, leggings as pants, even no pants at all.

These days on Substack, there’s a legion of writers with similar idiosyncratic inclinations (each in varying degrees of wackiness). Many of them picked up where ManRepeller left off when it folded in 2020, leaving a void for individuals making ostentatious fashion items relatable by mixing them with everyday scores—and blogging about it in a down-to-earth manner.

Bradshaw’s penchant for quirky headwear manifests among Substackers like Jalil Johnson, a shining beacon of personal style. The wackiness continues in big baubles and silk head scarves donned by ManRepeller alum Harling Ross. Fashion-editor-cum-fashion-Substacker Laurel Pantin recently paired sweatpants with a fringed tank and pumps. But each does so in a way that feels unique.

“I look at building an outfit the same way that you stage a movie or a theatre production: you have your lead actors, and you have your supporting cast,” explains Johnson. “You can't have a production with too many leads and you can't have a production with too many supporting actors, extras, whatnot.” A silly shoe requires an elegant trouser—“it's all about balance.”

Johnson notes that on TikTok, where personal style is fetishised in countless videos dictating the elusive formula for cultivating taste, Bradshaw and her style choices reign supreme. Her looks are more lauded now than when the show actually aired, he says, citing a recent conversation with an editor who worked at a major fashion magazine in the ‘90s and recalled a poor reception to many of her ensembles in the moment.

That said, there’s no denying Bradshaw had a style that was uniquely hers. “When I think about personal style, which is another conversation that I think we've reached the apex of, there isn't really a formula for it,” says Johnson. “Personal style and taste are all things you have to develop with the life you're living, what you're digesting. It's just a natural process. And I think Carrie, actually, all the women on Sex and the City are great examples because their clothes reflect the life they're living.”

This all stands in stark contrast to the quiet-luxury, stealth-wealth, old-money—or whatever you want to call it—movement still percolating in the ether. Last month in Paris, Kendall Jenner was lauded by minimalists for a look consisting of a concealed-button white linen tunic, pleated black trousers, black ballerinas, and, of course, The Row’s Marlo bag. There’s a whole breed of shopper infatuated with a distilled version of minimalist luxury brand The Row, composed of perfectly sleek silhouettes often divorced from the subtle wackiness of the brand itself. In this case, there is a formula for achieving the desired look—and in most cases, it’s going stale.

“Someone like (Medine Cohen) is a great antidote to that,” Johnson theorises. "It's not always about the perfect shirt or the perfect pant. It's about finding (yourself) and playing, which is a really scary thing to do as an adult.”

This attitude is as refreshing as the season three Carrie Bradshaw look in which she pins a supersized flower brooch to her white tank top, especially as we hit peak quiet-luxury. “I don't want to hear that word ever again,” he laughs. “It’s natural to yearn for something fresher, something unique, something maybe even a bit kooky.”

Lead image: Getty Images

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