If you’re like me, you may have grown up with the glamorous 2000s TV series Gossip Girl. I Love Dick shirt The show followed the lives of the overly dramatic, well-dressed Upper East Side teenagers and their intertwined stories of sex and scandal, but 12-year-old me brushed past all of that to instead watch the characters on the show I admired—the teens’ fabulously opulent mothers. Lily van der Woodsen and Eleanor Waldorf aren’t just impeccably stylish, over-the-top fictional characters, though. Their real-life counterparts are some of the best dressed fashion people you need to be paying attention to. Enter the viral Ladies of Madison Avenue Instagram and TikTok pages. Created by trained womenswear designer turned documentarian Joshua Kamei, the man-on-the-street style account has risen in the ranks to become one of the best fashion follows of 2023. Sitting at just under 250,000 Instagram followers, Kamei takes his camera and travels to the hot spots frequented by the stylish, opulent residents of New York’s fashion crowd. Think Lincoln Center performances, charity galas, and, yes, Madison Avenue.

I Love Dick shirt, hoodie, sweater, longsleeve and ladies t-shirt

Unisex Tee

Ladies Tee

Long Sleeve

Hoodie

Sweatshirt

“As someone who is self-diagnosed as ‘chronically online’, I Love Dick shirt I’ve seen a lot of flash-in-the-pan trends over the past few seasons,” says Elinor Block, editorial lead at luxury fashion gaming company Drest, which enables its users to create infinite outfit possibilities in the metaverse. “The past year we saw Barbiecore, ‘blokecore’ and ‘tomato-girl summer’ emerge as some of the bigger, zeitgeisty aesthetics adopted by Gen Z and the TikTok crowd. And whilst some are rooted in major trends, when it comes to real life, there’s no doubt that longevity and items that work season after season are a bigger draw. “When playing with clothes in Drest, however, there’s definitely a different kind of approach I take to dressing. The virtual world allows me to style looks that I might not have considered before with more out-there pieces from high-octane brands such as David Koma or Balmain—I haven’t been able to stop thinking about that cherry-red, rose-covered dress that I spied on the S/S 24 runway. It gives me a chance to be more experimental and see how I can move that into my IRL wardrobe without taking too much of a risk.” This, dear reader, is what the modern-day dressing-up box looks like. As always, any piece you invest in, be it inspired by the trends below or otherwise, should only be purchased if you intend on keeping it in your wardrobe for a very, very long time. I’ve gone to great lengths to cherry-pick the ones that have a chance.

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