Luxury Watch Round-Up: Red Carpet Drip, AI Style and Wild Cards
From haute couture to horological clogs, here’s a rearview glance at May.
With 2025 already halfway behind us, (I know, can you believe it!?) May has shaped up to be a month where style and innovation caught up with each other. Between the Met Gala’s sharp suiting, Hailey Bieber’s watch dress, and a wave of AI-fueled upgrades, it was a busy one! And while the internet was busy, so was I… I’m working on something exciting for my paid subscribers this month, so tap in. In the meantime, here’s what caught my eye…
Suits, Sparkle, and Haute Horology
The Met Gala came and went in its usual blur of high fashion and unforgettable style. I’ll admit, I was hoping for more vintage moments and a few bold pocket watches to match the theme, but the girlies still showed up and showed out. Menswear and sharp tailoring have been owning the spotlight lately, so I was especially curious to see how the women would bring their own flair to a made-to-measure moment. The result? Structured, tailored, and styled to perfection.
Janelle Monáe stole the show in a razor-sharp Thom Browne look, finished with a custom monocle clock by Cameron Hughes and a pink gold Vacheron Constantin Fiftysix Self-Winding. Angela Bassett made her Met Gala debut in a bold blue Burberry suit, elevated by a Glashütte Original Serenade Luna. Doechii kept things clean and refined in Louis Vuitton, tied together with an 18k gold Tiffany Eternity watch that felt modern, luxurious, and completely her. And of course, we can’t forget our sporty queens: Serena Williams and Simone Biles, both wearing the Audemars Piguet Royal Oak Mini Frosted Gold in white gold. Sparkling, strong, and unapologetic, just like them.
Hailey Bieber also turned heads at the Met Gala, donning a vintage Audemars Piguet in white gold with an opal dial. Her watch game is on fire right now! The newly minted billionaire founder also wowed in a Marine Serre piece from its Fall 2025 collection. The dress is an avant-garde design made entirely from 500 silver metallic watch straps. Not something you’ll see every day, but a bold statement, no doubt. She finished the look with a Mini Frosted Gold Royal Oak. Did I mention that’s the “it girl” watch of the moment? Yeah.
AI, But Make It Fashion
AI took center stage this past month, with shopping related announcements dropping from just about every major player: Google, Walmart, eBay, you name it. But it was eBay’s update that really caught my eye. In their words, they’re “pairing agentic AI capabilities with eBay’s scale, infrastructure, decades of customer insights, and product knowledge to streamline the experience for our customers.” Translation? They’re evolving to create an experience that interacts with you, anticipates what you want, and adapts in real time. For fashion lovers, the implications are exciting.
Watches, for example, are such an emotional purchase. It’s not just about price. It’s about the story, the styling, the vibe. AI could soon help people filter vintage finds by mood and aesthetic, compare a $300 gem with a $3,000 grail, or even generate a wrist shot of that dream Cartier from the tap of your phone. A more tailored, seamless, and surprisingly fun shopping experience could be just around the corner.
When it comes to accessories like watches and jewelry, we’re not quite there yet, but the groundwork is being laid. I'm especially curious about what this means for personal shopping, styling services, and how luxury brands deliver curated experiences through tech. If you’re already tinkering with any of these tools, I want to hear all about it!
Fresh Drops and Wild Cards
We couldn’t wrap May without a few fresh drops worth mentioning. First up: the Blancpain Ladybird Colors in Royal Purple. It’s a regal revival of the 1956 classic, complete with over 2 carats of hand-set diamonds, a luminous mother-of-pearl dial, and Blancpain’s signature moonphase complication. I saw her up close recently, and at $38,000, she’s every bit the queen she claims to be. On the more accessible side, Frederique Constant debuted the Manchette, a sleek cuff-style watch that perfectly bridges fashion and horology. Starting at $1,395, it made quite the impression on me at Watches & Wonders.
Switching gears to collabs, the Dennison x Collectability Sunray Dial stands out. A limited-edition piece created in partnership with Patek Philippe expert John Reardon and designed by none other than Emmanuel Gueit (yes, the genius behind the Royal Oak Offshore). Dennison has been dropping some serious bangers since last autumn and this latest edition continues that momentum. At $690, it’s a collector’s gem at a relatively accessible price. We love it! And for the wild card: Casio and Crocs teamed up on a G-Shock x Echo Wave clog collab, complete with a marbled glow-in-the-dark strap and a modular watch face that snaps on or off the shoe. It’s priced at $200, and while I love a good watch-shoe moment (Cristian Cowan x Zanotti will forever be a fave), this one’s... a choice.
That’s it from me for now. See you next time!