If you’re like me, you may have grown up with the glamorous 2000s TV series Gossip Girl. Philadelphia Baseball You Just Got Daycare’d T-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.

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With everyone from our favourite emerging brands like I.Am.Gia and Philadelphia Baseball You Just Got Daycare’d T-shirt Miaou to heavy hitters in the Tibi and Rosie Assoulin category pushing plaid for this season, our favourite influencers, editors, and trend setters have definitely gotten the memo. It’s no surprise, then, that I had such trouble narrowing down my favourite street style shots in the classic print to a mere 13. Not to mention the will power it took to curate my dozens of plaid products I’m loving right now to a more-digestible number under 20. Nonetheless, I did it, and the result is a seriously inspirational group of plaid-covered outfits you’re going to want to copy ASAP. Luckily, you can because—not to brag, but—I think you’re going to love the shopping picks we narrowed down for you. But enough of my trying to convince you. Simply see for yourself below. Off-the-shoulder tops for summer are a fashion phenomenon unlike any we’ve seen before. The second this trend was called out, it seemed as though every single retailer’s racks were filled with shoulder-exposing styles that they couldn’t keep in stock. With the rapid expansion of a trend like this, it seems only natural that it would eventually die down, but exactly the opposite has happened with the off-the-shoulder craze. Since its debut, the style has evolved to take the form of a variety of new silhouettes that you absolutely must know about. It’s no longer just about the straight-across style—there are one-shoulder, cutout, asymmetrical, and strappy counterparts that are just as stylish.