Mark Zuckerberg, who used to meet investors in a hoodie, has upped his fashion game such that he went from Silicon Valley’s most notoriously underdressed CEO to commanding the front row in Prada fashion show right alongside Anna Wintour

Image - Instagram / zuck


Mark Zuckerberg has come a long way from being the boy at Harvard to becoming the world’s fourth-richest tycoon, worth around $225 billion. The same can be said about his wardrobe, which has metamorphosed from a rotation of drab, unchanging grey T-shirts to runway-ready Prada. The Meta boss and his wife Priscilla Chan were recently spotted sitting in the front row at the Prada fashion show. This Silicon Valley billionaire had never graced Milan Fashion Week before, and perhaps Priscilla’s birthday was the perfect occasion to grow up a little and do something new. They certainly did, attending Prada’s Fall/Winter 2026 women’s show in Milan, dressed head to toe in Prada.

Zuckerberg and Chan slip into tourist mode outside the Milan Cathedral. Image – Instagram / zuck

The power couple, who run the Chan Zuckerberg Initiative and are parents of three, arrived shortly before the show began, accompanied by Anna Wintour and Eva Chen, Instagram’s director of fashion partnerships. They were seated alongside Lorenzo Bertelli and Prada CEO Andrea Guerra. Intentional or not, they clearly stole the show without trying too hard. Zuckerberg wore a taupe knit polo with brown trousers and chunky black Prada loafers. Chan wore those loafers too and teamed them with a grey sweater, navy separates, and a diamond necklace.

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Letting the Prada triangle on their backs do all the talking. Image – Instagram / zuck

It became increasingly obvious that they wanted to draw attention to the Prada brand; first by the simple fact of their presence, second by taking the trouble to shoot a reel on Instagram to promote their trip, and third by using Meta’s Ray-Ban glasses to film a back-view shot of themselves wearing Prada. This is not a newfound love of fashion, but the continuation of a long-standing love of business. It could well be the genesis of a partnership between Meta, Prada, and EssilorLuxottica for Prada-branded AI eyewear, on top of Meta’s existing Ray-Ban Meta collaboration.

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The Milan trip doubled as a work visit and a celebration of Priscilla Chan’s birthday. Image – Instagram / zuck

According to Rai News, when Miuccia Prada was asked point-blank backstage about a possible Meta x Prada smart-glasses partnership, she replied, “Maybe, who knows.” The couple’s first time at Milan Fashion Week seemed truly memorable, as the tech tycoon captioned a post, “Thanks to Prada for having us in Milan!” with a carousel of their good times. In between front-row duty, they slipped into full tourist mode, posing in front of the Duomo and tucking into a classic cotoletta alla milanese, with Priscilla’s birthday cake also making an appearance on his feed. On the business side, Meta has been working with the EssilorLuxottica eyewear group since 2019, and the second version of the Ray-Ban Meta glasses came to market last year with updated AI capabilities. Guess it is time to mix a little more high fashion with technology. Only time will tell, but the signals are definitely there.

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