16 Comfortable Boots That Will Help You Survive Any Type of Weather This Winter
Sponsor Content Created With Fitflop
Yesterday I received a frantic text from an East Coast friend: "It's pouring rain and I have a date. What do I wear?" Whether it's an important event or just your daily walk to work, choosing an outfit that won't leave you drenched can be a struggle.
My answer to my friend's dilemma? An umbrella and a good pair of boots—weatherproof ones, to be exact. I like to have a pair that can survive anything, and FitFlop have tons that check all the right boxes: fashionable, comfortable, and weather resistant.
Keep scrolling to shop the essential items (you can score 20% off your first order with code NEWADDICT!) that'll leave your feet dry and warm, even on the most drizzly days.
RAIN-APPROVED
Perfect for that rainy day coffee excursion, sans the soaked socks. (Or for when you want to splash in puddles as an adult—I don't judge.)
SNOW-APPROVED
Boots that come in handy when your commute to the office is a little icier than usual.
EVERYDAY-APPROVED
Sunny? Windy? Cloudy? Doesn't matter. Throw on any pair of these comfortable boots and you'll be sure to conquer the day.
Up next, 17 Outfits to Wear With Your Black Ankle Boots

Anneliese Henderson is a New York–based senior editor on the branded content team at Who What Wear where she covers the latest in fashion, beauty, and lifestyle. When she’s not writing about her favorite trends, you can find her reading romance novels or running around the town with her Bernese Mountain Dog, Rosie.
-
Listen, Being Cool in 2025 Requires Just Two Things: Loose Jeans and This “Weird” Viral Flat-Shoe Trend
They're strange, but so chic.
-
My Mom Is in Her 50s and Asked Me for Fashion Advice—8 Chic Nordstrom Outfits I Put Together for Her Under $425
Outdated prints and "ugly" shoes included.
-
These Easy Outfit Formulas Make Even Fall's Most Polarizing Boot Trend Look Cool
See the inspiration inside.
-
This Is the Luxe Fall Shoe Trend Every Fashion Person Is Already Wearing on Repeat
Count these inspo pics as proof.
-
Fashion People Have Been Waiting for the Alex Eagle x J.Crew Launch—29 Chic British-Meets-American Pieces Worth Scooping Up Now
Wait until you see the sneakers.
-
Calf-Hair, Suede, Espresso—30 Luxurious Nordstrom Items I'm a Little Too in Love With
Simply stunning.
-
It's Controversial (I Know), But Frequent Fashion Flyers Swear By This Jeans Outfit for Long Flights
It involves an elegant leather coat and chic luggage.
-
A Definitive Guide to the 21 Best Wallets Money Can Buy
It's time for an upgrade.