I’m Calling it Now: 2026 Is The Year of the Fun Hat

For those of us who dared to attempt a Hailey Bieber-inspired bob this winter, rest assured there’s a trend to help distract as we work our way through the awkward grow-out stage. Hats are having a moment that extends far beyond the practical uses of keeping warm or shielding one from the sun’s harmful rays. And as a self-described lover of over-accessorizing, I couldn’t be more thrilled.

Headwear was once a staple in every woman’s wardrobe, as necessary as a pair of stockings or a handbag. In the 1920s, you were highly unlikely to see a woman running errands bare-headed. Now, you might reach for a knit beanie when the temperature drops or a straw sunhat on vacation, but it’s not considered a must, not even as a finishing touch to a look. Still, they’ve played a pivotal role in countless iconic style moments (think: Jackie O.’s signature pillbox or Bianca Jagger’s bridal sunhat), and It Girls have slowly been embracing them online and in street style. This is looking to be the year hats come back in a big way, and I’m ready to add a few into my regular rotation.

So, which hats are worth your while? Above all else, go with the styles you feel flatter your face and head shape. Then, pay attention to what realistically complements your existing wardrobe, as well as time of year and temperature in your region. (You might not need or want to wear a cashmere beanie if it’s always sunny and 75°.)

In New York during the winter, I’ve found myself gravitating towards structured wool and felt styles, especially pillbox and fez hats. I got this one from Cos before the holidays, and I love the way it adds a touch of vintage romanticism to days spent bundled up.

I’m also planning to place a large order with Lele Sadoughi; though the brand is known for headbands, I was surprised to find quite the array of wool felt pillbox hats on site. (I’ve already got my hands on the classic black, but the leopard and lavender are both waiting patiently in my cart.)

In a similarly vintage vein, a felted wool cloche is high on my wish list. Think of this as the humble bucket hat’s elevated older sister. It’s a similar shape, but more fitted and structured than floppy, and the brim does little to actually shield from sun. I’m eyeing the camel Madewell pick below, but only time will tell if I can successfully pull this one off.

Knit cloches are a slightly more wearable option I’m seeing a lot of, too. One part bucket hat, one part beanie, all parts cute.

Perhaps the top-trending style of the season is anything with a bit of faux fur or shearling. It’s a good alternative to a furry coat, if that intimidates you. Paired with classic wool outerwear, these hats still give you that luxe winter look—less Abominable Snowman, more après-ski diva. I have this one from Aritzia in multiple colors.

I feel I must call attention to the sportiest hat of the moment: the fitted beanie. On me, it feels too snowboarder, but I swear it can give "Cameron Diaz in an Early 2000s Rom-Com" with the right outfit. If you also feel like the look leans a bit skullcap on you, go for one with a cuffed edge, like this style from Vince.