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If you’re like me, you may have grown up with the glamorous 2000s TV series Gossip Girl. Donald Trump Take A Look What Happened I Don’t Die Easily 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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Just a quick glance at Barbara Martelo’s Instagram feed and there’s no denying she’s a huge fan of pointed-toe shoes. Donald Trump Take A Look What Happened I Don’t Die Easily T-shirt From mules to flats to pumps and ankle boots, the fashion editor and consultant has made the sleek style an integral part of her incredibly chic wardrobe and we’re paying close attention to how she pulls them off. She is one of the top street style stars each season after all. Martelo is known for her effortless-meets-edgy outfit formula, which is comprised mainly of blacks, whites, and grays. However, as we see in these shots, the main piece she wears when donning a pair of cool pointed-toe shoes is a pair of skinny jeans in a variety of colors, washes, and hem styles. Choosing a stylish sneaker for a non-athletic outfit walks a fine line: Too sporty may not look sophisticated enough with your favorite dress, and too simple can sometimes look unrefined. New Balance’s classic sneaker collection hits the sweet spot, with a wide range of retro-inspired shoes that call upon vintage athletic styling details. Plus, the look easily complements a midi-length skirt or trousers for a street style vibe.