I Can’t Stop Thinking About These Flirty Little Hats

Many men are comfortable in hats, this much we know. Take the baseball cap, for example—one of few accessories that even the most fashion-averse man needs no convincing to wear. (Ever gotten flack because you refused to take off your Aimé Leon Dore or UMich hat inside of a church or nice restaurant?) The style has enjoyed a long, unchallenged lease on men’s cranial real estate at large, only ever sharing the space with its variants, such as the snug, good-boy ballcap, the lofty, dirtbag trucker, and, during frosty seasons, the beanie.

And now, ever since Miuccia Prada and Raf Simons showed Prada’s fall 2026 menswear collection in Milan earlier this week, it seems possible that a nostalgic silhouette may soon take up residence in the ultra-exclusive neighborhood of head-topping men’s accessories: the flirty, cocked newsboy cap.

Tweedy, lopsided newsboy caps and floppy, mini bucket hats dotted several of the looks on the Prada runway. (Some models had hats that looked like they’d been plastered onto the backs of their outfits, as if they’d literally slept on them overnight.) The hats accessorized outfits that included thick, wooly overcoats with eroded edges, low-cut, colorful threadbare tees. Warm, but not nearly warm enough. All together, the collection had the sweetly sad, proletariat charm of a wayward boy kicking rocks on an overcast day.

The newsies cap, in particular, stood out, as it was positioned in such a way that it partially concealed models’ faces, casting a slight but cinematic umbra. For whatever its worth, many of the baby-faced stock brokers in my neighborhood tend to style their capacious baseball caps in a similarly askew fashion, their expressions muddied by the shadow of their hat’s brim. It gives their otherwise fratty vibe a bit of a mysterious edge, like they’re keeping some thoughts close to the vest.

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