This article was written by The Zillennial Zine’s spring editorial intern Erin Galioto. Find her on Instagram at @eringalioto. If you would like to share an article with The Zillennial, send us an email at thezillennialzine@gmail.com.
Do you ever put on an outfit and feel “If I was a cartoon character, this is exactly what I’d wear,”? To me, this moment is the most thrilling part of personal style. To achieve an outfit that captures not only your authentic self but also a childlike sense of whimsy is no easy feat. Every season I search incoming trends and runway styles to find pieces that help me achieve this. In the past, I have represented my cartoon soul with 8-inch Demonia boots, pleated mini skirts, and hair bows, but those styles have run their course. I’ve been craving something fresh and exciting to add that little bit of spice to my outfits and communicate to strangers at the coffee shop that I’m cool, I’m fun, and I’m free. Enter silly little hats.
I have formerly taken a very anti-hat stance. Brimmed soft felt hats screamed Christian-girl autumn, big woven sun hats seemed like an overstimulating hazard, cowboy hats felt corny, and baseball caps never quite looked right. Recently, however, my hat convictions are wavering. I now realize that I have been far too narrow-minded and the headwear universe spans miles farther than I’ve ever considered. Last summer, after some Pinterest inspiration, I took on the ambitious task of crocheting a beaded cap to wear to a music festival that same week. Insane, I know, but the result was shockingly better than expected. Not only did I successfully finish the project in time, but the cap was the perfect whimsical finish to my look and how I felt as the dangling beads danced with me was nothing short of magical.
As the newest cap cult convert, I was thrilled to see more brands reinvent these former costume pieces into chic fashion accessories and I can hardly wait to join the party. From captain hats to medieval bonnets, there’s a whimsical hat out there for everyone. Join me in exploring some of the latest it-girls in the hat roster as well as some tips on how to style them:
Aye, aye, captain!
Baum und Pferdgarten released their Copenhagen Spring 2024 collection featuring embroidered sailor caps in white and navy— and I lost my mind. The nautical headpiece is so crisp and classic that it can seamlessly mesh with any outfit. At the same time, its unorthodox nature instantly sparks interest as it toes the line between costume and character. For an instantly chic outfit, try mixing the playful cap with more formal or tailored pieces. Stylist and fashion legend Natalie Guyette (@natacatatat on IG) paired her sailor hat with layered tanks, a black maxi pencil skirt, a pooka shell anklet, and orange flip flops and the end result is chef’s kiss!
Queen of the Castle
I always regarded the paper crowns I constructed in kindergarten as a fun, wearable craft project, not a fashion statement. I now realize my deplorable ignorance thanks to the Montreal-based company Nina Bow. Nina Bow has been on my radar since their debut of ludicrously capacious bags, dubbed The Franky, that every iconic fashion influencer seems to be toting. Their latest drop in collaboration with model Florence-Émilie Morin (@____fem on IG) features sewn fabric crowns in many different textiles. The red and black tweed crown might be my favorite and gives a very “Junie B Jones for Chanel” vibe. The crown has some serious star power and I hope to see more of these in the wild. Obsessed!
Lil Bo Peep Chic
Coquette lives on!!! You thought bows were overdone and cottagecore would disappear? Big mistake. Little House on the Prairie is back with a vengeance and their accompanying bonnets are all the rage. The bonnet is the perfect headwear for transitioning between the coastal grandmother babushka and the heavy-knit balaclava. The Handmaid’s Tale staple can be worn tied snugly in a bow for the girlie who has her sh*t together or with strings untied framing the face for the ones who like to let loose. Cutesy, doll-like accessories not your thing? Opt for a bonnet with hardware like Rabanne’s grommet-laden head scarf or take inspo from Amber Strickland’s (@amby.strickland on IG) chainmail bonnet.
Swim Team Slay
Remember Yankee with no brim? This is her now, feel old yet? FFORME released a collection for Fall 2024 featuring skin-tight, beanie-esque headwear that resembled swim caps. Other versions, like this off-white beanie from Jacquemus, even feature a chin strap. To me, these hats feel like an extension of the wide soft headbands that gained popularity last year, with a little more coverage. Synchronized swimming was a hit at the Paris Olympics and there’s no reason you can’t add those vibes to your fall wardrobe. Wear it over the ears with big sunglasses for a locked-in, world-out vibe, or try a more structured version to add a vintage feel to your streetwear.
Paddington Bear Core
Caro Editions released an eclectic circus-inspired collection for Copenhagen Spring 2025 that paired a matching dome-shaped, short-brimmed hat with every look. These hats are a cross between a fisherman’s hat and a bucket hat and have an inherit quirkiness to their shape. The range of colors, prints, and textiles is enough to bring rainy-day functionality to everyday style, and designer Caroline Bille Brahe’s styling brings Paddington Bear’s get-up to shame. As a former bucket hat enthusiast, these fanciful caps feel like their eccentric, well-traveled older sister. Pair it with a one-piece bikini for your last pre-fall trip to the beach or with a trench, baggy pants, and flip-flops for on-the-go.
Wondering how to style hats this fall? Whether it’s hair clips, headbands, or a funny little hat, headwear is an amazing way to spice up a look and give your style some depth. Which silly little hat will you be sporting and how will you style it? Let us know in the comments below!
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