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. 


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.)


Boots that come in handy when your commute to the office is a little icier than usual. 


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
Senior Editor, Branded Content

Anneliese Henderson is a Los Angeles–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 a book by the beach or spending money on overpriced smoothies at Erewhon.