The rainy season is often associated with spring, but if you’ve ever experienced an east coast fall, you’d know it’s anything but dry out there. In fact, I’d argue that autumn is one of the wettest times of year: Between the unpredictable downpours and high winds often caused by the tropical storms in the south, teamed with the increasingly cooler temps, NYC fall weather is not for the faint of heart—which means dressing accordingly is crucial.
For starters, you’re going to want some sort of weatherproof topper that repels water, like a rain slicker, trench coat, barn jacket, even an anorak. If your jacket or coat doesn’t have a hood, then you’ll need something to shield your hair. For those who can bare to carry them and are responsible enough to not constantly lose them in Ubers, umbrellas are helpful. But if you’re looking for an alternative that won’t fail you in rainy conditions, consider a rain hat.
Unlike an umbrella, a hat made of water-repellent nylon or vinyl is hands-free and offers full-head protection without the fuss. It also adds a stylish element to just about any look, and can take a blah rainy-day outfit and give it personality.
One of the more popular options to wear as of late come in the form of bucket hats, which offer extra protection thanks to a wide-brim radius. And like your favorite crochet bucket sun hat, it’s super versatile and easy to style. Take the street style examples below: You can go for a tonal look, opting for a hat that matches your jacket or accessories, or you can go for a bright color in patent to liven up your look. If it has chin straps, even cuter.
Chin straps will help keep your bucket hat in place on windy days.
A coordinated look will help you look put-together. Bonus points if it’s bright!
Shop Rain Bucket Hats
Burberry Reversible Gabardine Bucket Hat
Eric Javits Patti Bucket Hat
Prada Re-Nylon Bucket Hat
Janessa Leone Shiloh Rain Bucket Hat
Now 25% Off
Helen Kaminski Frankie Water Repellent Cotton Bucket Hat
For those who prefer to keep their look more stealth, take a page out of Kendall Roy’s fashion playbook and reach for a baseball cap. Those kind of rain hats are great for drizzly days and pair perfectly with casual outfits, like jeans and a tee.
Shop Rain Baseball Caps
Loro Piana Baseball Cap – Cashmere Storm System
Hat Attack Classic Rain Cap
Stilksen 107 Ventile Moss
Or, alternatively, you can channel babushka vibes and wear a retro bonnet that adorably wraps under your chin—a go-to look for the late Queen Elizabeth during rainy days at the horse track.
Queen Elizabeth often wore waterproof bonnets on rainy days.
Shop Rain Bonnets
Rosarium Nimbus Rain Bonnet in Sage
Rain Waterproof Headscarf
SelfTek Rain Bonnet with Visor
Tata Berthe Rain Hood in Water-Repellent Burgundy Fabric
The rain hat options these days are truly endless—and with fall officially here, there’s no better time to start shopping than now.
Sophie Dweck is the Shopping Editor for Town & Country, where she covers all things fashion, beauty and lifestyle, shares her expertise on the most worthwhile luxury products, tests and writes in-depth reviews on the very best essentials worth investing in, as well breaking news about the latest launches, and of course, reports on the biggest sales and deals to shop no matter the day. Some of her favorite items to date are Gwyneth Paltrow’s ski trial cardigan, the Hotel Chocolat Velvetiser, and ZIIP’s microcurrent device. When Sophie isn’t testing state-of-the art beauty tech or breaking down TikTok aesthetics, she loves indulging in BonBon sweets (Sorbisars, for the win!) and finding the next trend before it goes viral.
