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Key Takeaways
- Hats are the latest accessory to get the statement treatment, with styles like crocheted skullcaps, berets, and cloches all becoming top trends.
- Given several funky little hats are trending at once, it’s all about finding one that appeals to you and styling it with other playful accessories for maximum whimsy.
When it comes to accessories, bags and jewelry have a reputation as instant statements, but one oft-overlooked piece is getting its moment in the sartorial sun. Hats are back at the forefront of fashion’s most creative trends, and the funkier, the better.
If you’ve been keeping up with fashion month, you might’ve noticed a few unconventional toppers both on and off the runway. So, we’re calling it: In the spirit of whimsy-maxxing, c*nty little hats are taking over the crowns of tastemakers. The clean girl-approved baseball cap is still around, albeit slowly being put to pasture as bejeweled skullcaps and retro-inspired cloches grow in popularity. Considering that autumn (also known as peak hat season) is just getting started, you can expect to see more statement caps making their appearances as the year wraps up. Ahead, learn everything to know about the eclectic hats taking over everyone’s closets, plus styling tips and standout picks to shop.
About the Trend
From the 1920s flapper era to the mid-aughts Von Dutch trucker hat, some form of a playful hat always makes its way into fashion. But, with the early-to-mid-2020s dominance of quiet luxury and minimalism, the funky hat was tucked away for more subtle headwear like the aforementioned baseball cap and Carolyn Bessette Kennedy-inspired headbands. As the desire for neutral-toned, conservative dressing died down in spring 2026, whimsy-maxxing blossomed with its array of colors, patterns, and “curated chaos.” Of course, with a maximalist closet comes striking accessories, and thus, playful, freaky little hats came back into fashion.
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What qualifies as a funky hat? While some hat options automatically fall under the umbrella of whimsy (which we’ll get to), there isn’t a specific type of hat that owns the moniker—and that’s the beauty of this trend. Any brightly colored, playfully patterned option fits the bill, which allows wearers to personalize the trend in just about any way they see fit. Just like other aspects of whimsical dressing, it’s all about embracing your individual styling approach.
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The Appeal
As mentioned earlier, this season’s most spectacular caps are all rooted in the zeitgeist’s current taste for whimsy. Think playful colors, patterns, and prints that err on kitschiness, similar to the styles that were in fashion during the early 2020s. Think of whimsical dressing as the antithesis to quiet luxury: Consumers simply grew tired of beige basics, so they steered away from neutral-toned closet staples and towards full-fledged eclecticism. The appeal of whimsy-maxxing only grew bigger as independent labels like Collina Strada and Sandy Liang leaned further into the trend, as did Marc Jacobs, which has had a major resurgence in popularity in recent seasons.
@collinastrada / Instagram
As for hats themselves, the trend is certainly still budding amongst fashion labels. That being said, Thom Browne recently embraced it for spring 2027 in the form of teensy fedoras paired with striking bobs. Though the trend is still developing on the catwalk, playful headwear has become a full-blown trend on the streets of SoHo, Copenhagen, and more on a global scale.
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The Moment’s Best Funky Little Hats
While any topper with a playful color, pattern, or silhouette can fit into the funky little hat trend, a few styles are standing out this season. Ahead, we’ve rounded up four key types to help you get started on your search.
Skullcap
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Not too long ago, skullcaps were seldom spotted. Now, they’re everywhere, thanks to their whimsical approach to headwear. These lightweight caps lay right over your crown and have a more snug fit than most hats. What makes them so appealing in the age of whimsy dressing is the array of fun options to choose from. One of the most popular styles is crocheted, but they also come in stunning beaded options that can elevate any outfit you pair them with.
Beret
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Give your wardrobe a subtle Parisian approach with a beret. This 1990s favorite has recently crawled back into mainstream fashion for its romantic take on whimsical accessorizing. While most berets have a modest, pared-back style, they still come in a rainbow of colors to zhuzh up your wardrobe without diving into maximum levels of kitsch.
Pillbox
@magnolia__ave / Instagram
This retro hat is making a huge resurgence for its more structured approach to headwear. Unlike the looser, more fluid structures available, pillbox hats will always sit up straight and have a flat crown with little movement. Modern versions are pairing the structured, vintage-inspired silhouette with unexpected patterns like animal print and raffia. Style it with textural moments and other statement accessories for maximum impact.
Cloche
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Think of the cloche as the elevated sister to a bucket hat. This bell-shaped hat—which sits snugly on your head and features a brim that slightly blooms outward—is another vintage style making a major resurgence. Its shape alone already makes a statement, so it’s one of the few options that conveys whimsical dressing even in a neutral tone like beige, gray, or black.
How to Style
The beauty of this trend is that there’s no singular way to style it: A funky little hat qualifies for just about every outfit and event. That being said, there are a few ways to approach the look with an elevated eye.
You can pair your hat with an everyday look (think jeans and a white tee, trousers, or a solid colored dress) to make it the statement piece of your outfit. For a more amplified take on whimsy dressing, try pairing it with clashing colors and prints for a vivacious wardrobe.
Your other accessories come into play, too. If you want a streamlined outfit, add a bag or pair of shoes that matches your hat. Alternatively, opting for bold jewelry, scarves, or other accent pieces can amplify the maximalist energy in the best way.
The Best Funky Little Hats to Shop
The best part about this trend? You don’t need to pay luxury prices to enjoy it. From classic berets to statement skullcaps, your headwear options are practically endless—and budget-friendly. Below, check out our edit of whimsy-fueled hats that bring a breath of fresh air to your wardrobe.
