We’ve Entered An Age Of Quirky & Outlandish Hats

Though laid-back athleisure has been at the forefront of fashion over the past few years, the pendulum is decidedly swinging back to all things glamour. Yes, ready or not, we’re entering an era of getting overly dressed up (with absolutely everywhere to go). As such, quirky, one-of-a-kind hats, particularly vintage — and vintage-inspired — silhouettes, are a defining part of the style scene right now. Suddenly, nearly every member of the fashion pack, from designers to influencers, is giving the whimsical, not-so-serious look their seal of approval.

The decades-old style hit its stride during fashion month this season, where some of the industry’s biggest players presented their takes on classic hat silhouettes. In New York, Alturzarra, which just celebrated its 15th anniversary, showcased a host of black and white pillbox silhouettes, a look Jackie Kennedy brought to prominence in the ‘60s. Over in Milan, Loro Piana, too, sent models out wearing pillbox iterations, ranging from a brown herringbone piece to a burnt orange version. Also at MFW, Prada debuted an outlandish assortment of hats, which sparked plenty of buzz on the internet. Co-creative directors Miuccia Prada and Raf Simons doubled down on vintage-esque styles, including flat caps and newsboy looks festooned with details like feathers and flowers. Then, there was Jil Sander’s ‘20s-era embellished creation, which was dripping in crystals.

On the sidewalks, Laura Reilly, a fashion writer and brainchild of newsletter Magasin, captured the attention of street style photographers, as well as showgoers like myself, in her structured white hat from The Row. (It was the exact style Greta Lee wore to the 2023 SCAD Savannah Film Festival.) Meanwhile, another fashion week attendee accessorized her look with an of-the-moment pillbox style adorned with a veil.

Of course, these new designer looks will cost you a pretty penny. Another alternative? Checking out the secondhand market, which is chock-full of amazing decades-old styles at a fraction of the price. (‘Oh, it’s vintage!’ These three words are the ultimate fashion flex, we might add.) If you’re going this route, look to influencers for shopping guidance. Jenny Walton, for one, is no stranger to a thrifted hat. In the TikTok below, the creative shares a wacky, fringe-y silhouette she scored from Happy Isles, a consignment shop located in Los Angeles and New York. “Vintage hats are unhinged and I’m here for it,” she wrote in the caption. She’s not wrong — these blast-from-the-past pieces are a bit out there, but that’s what makes them so captivating.

Rachel Seville Tashjian Wise, a fashion writer at The Washington Post, likes to scout Etsy for her statement headwear. Below, Wise wears an outsized, eye-grabbing brown Schiaparelli hat she found from the online market. She also turned to the site for a black cocktail style, which she donned in Paris last October.

Sure, you could spend hours tracking down vintage hats online (the hunt can be quite thrilling), but instead, we did all the leg work for you. Ahead, find 10 of the best styles to pick from — and because they’re one-of-a-kind, don’t sleep on something that catches your eye.