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 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.
-
It's Officially a Butter-Yellow Summer—27 of the Chicest Finds at Zara, Nordstrom, and J.Crew
Fashion people love this color trend.
-
This Nordstrom Rack Sale Has So Many Cool-Girl Essentials—These 25 Finds Are the Standouts
An extra 20% off? Yes, please.
-
The Classic Hero Piece That Fashion People Reach For All Summer Long
Something for every personal style.
-
I've Lived in NYC, L.A., and Boston—Here's Everything I Think Is Chic for Summer
Shop the highly curated list.
-
The Perfect $16 Tank Top and More Zara Items I'm Texting Everyone I Know About
Elite finds.
-
The 30 Items That Will Define Style in Summer 2025
Gotta catch 'em all.
-
Linen Pants! Full Skirts! Long Shorts! Zara Has Every Single Chic Bottoms Trend—40 Picks That Are Worth Your Attention
Good luck picking just one.
-
3 Aesthetic Pairings to Try If Your Wardrobe's Starting to Feel Stale
Foolproof solutions.