FYI: If You Wear This Dated Sneaker Trend in Fall 2025, Make Sure It's With Baggy Jeans

In 2025, retro-inspired, low-profile sneakers remain the top sneaker style. However, another sneaker trend is re-emerging, reminding us that fashion is cyclical and trends rarely disappear—especially when its revival is backed by a celebrity. Enter high-top sneakers. Yes, you read that right. The old-school and somewhat controversial silhouette has resurfaced, spotted on Gwyneth Paltrow this week.
In case you missed it, Paltrow was seen in Milan the other day with her husband, Brad Falchuk. She wore a casual yet chic outfit that included a polo sweater layered over a button-up shirt, paired with wide-leg, baggy jeans and high-top sneakers, specifically Adidas's Jabbar Hi shoes. These sneakers were originally designed for former basketball player Kareem Abdul-Jabbar in 1978.
Paltrow could have styled her sneakers with any denim trend, but her choice of baggy, wide-leg jeans makes perfect sense. Both the jeans and the sneakers have roots in streetwear and the Y2K era, making them an ideal match. That said, if you're going to get on board with the high-top sneaker trend resurgence this fall, make sure to style them with baggy, wide-leg jeans. Keep scrolling to discover Platrow's outfit, and shop the best baggy jeans and high-top sneakers.
On Gwyneth Paltrow: Adidas Jabbar Hi Shoes ($88)
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According to designers like Prada, Tory Burch, and Toga, preppy polos are a wardrobe essential.
Shop Baggy Jeans and High-Top Sneakers
Everyone is reaching for suede sneakers right now—and for good reason. The style lends a very rich vibe.
Free People has just launched its new We the Free jeans, which feature a high-rise, rigid denim fabric, and a slightly loose fit.
Nikki Chwatt is an associate fashion editor based in New York City. She joined Who What Wear in 2024 after writing fashion, beauty, and lifestyle content for WWD, Well+Good, Editorialist, and more. With a passion for personal style and the creativity that comes with it, one of Chwatt's goals is to help others understand that there is no such thing as a “good” or “bad” style; it’s just about putting an outfit together that makes you feel confident in yourself. When she's not writing, you can find her taking a Pilates class, reading a powerful romance novel, or exploring a new wellness spot in Manhattan.
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