With a pumpkin spice aroma filling the streets, leaves falling from the branches, evenings growing cooler, and breezes picking up, you know autumn has officially arrived. Although fall in the city is especially magical for the aforementioned reasons, the season does welcome more rainboot weather. In fact, New York already got a head start on precarious precipitation patterns, thanks to the many dramatic downpours the city faced almost every weekend this summer. But a little rain doesn’t have to mean sacrificing style. It’s time to embrace the colder, wetter months with some new stylish umbrellas and outfits to match.
Rainy-weather dressing doesn’t have to be bulky or tasteless. In fact, selecting pieces with functionality in mind can make getting dressed even more exciting. The key is to try new things and not be afraid to layer your look; the more the merrier — because no one wants soaked clothing or wet feet. The goal: stay dry, stay warm, and feel fabulous while doing it.
It’s easier said than done, so to make sure I got it right, I went all in — styling an array of fall fashion ‘fits for just about any occasion. Of course, you can swap anything in or out to make each ensemble work for you. Below, see my takes on making an outfit both functional and fashionable for those less-than-ideal weather days.
Cool & Casual
Isabel Choi
This fall look brought me so much joy and felt instantly nostalgic. Pulling out my Vera Bradley umbrella and classic Hunter boots brought everything together in the most charming way. Pairing this boat-style jacket with a soft baby tee and Levi’s icon denim felt classic, but with a playful twist. It’s the kind of look made for crisp fall afternoons amidst a dewy pumpkin patch. Comfortable enough to wear all day, but still thoughtfully combined, it captures everything I love about getting dressed for autumn.
Sporty & Chic
Isabel Choi
My favorite recent trend has been finding ways to make an athleisure look feel incredibly styled and intentional. This tracksuit was so lightweight and comfortable that it felt like pajamas. The Salomon Gore-Tex shoes added a practical touch — especially since they’re waterproof. The whole outfit gave me a ballerina-off-duty feeling: effortless, feminine, and a little unexpected. Smaller details like the scrunchie with dangling tulips and a Duckhead handle umbrella punctuated the look and made me feel put together and pretty.
Light & Airy
Isabel Choi
A lightweight nylon jacket is perfect for those humid, warmer days when you still want a little layer, and the colorways in this particular style are just too good. I paired my olive green-accented one with black-and-white Adidas shorts and the newly released Dr. Martens rain boots, which also come in a fun assortment of shades that instantly elevate even the simplest look. I finished it off with a few of my favorite accessories: my go-to handbag, a Barbour umbrella, and the softest, coziest socks for a little extra warmth.
Day & Night
Naomi Ludlow
We all need a look that moves from 9 to 5 and 5 to 9, and this outfit does so seamlessly. A darling high-neck dress set the foundation for this outfit, layered with an affordable faux-leather jacket for just the right amount of warmth. I also leaned into one of my favorite styling tricks: treating cheetah print as a neutral. These Melissa Wellies added a playful touch while contrasting with my clear umbrella, which kept me dry while adding an unexpectedly polished element to the look. Très chic, indeed.
Girls Night Out
Naomi Ludlow
You can’t let a little rain derail a girls’ night out. This look effortlessly transitions from drinks at the bar to an evening on the dance floor with karaoke. With nightfall also comes temperatures dropping, so I layered in a sweet polka dot raincoat from Damson Madder. For the rest of the look, I added a fun bubble-effect skirt that moved beautifully with every step, giving the outfit a little drama without feeling overdone. These boots also feature a subtle heel but are still fully enclosed, keeping the wind and rain away without looking clunky.
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