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.
-
Whenever I'm in Paris, I See This Boot Trend Styled With Minidresses in Every Vintage Shop and Local Bistro
Sorry, ankle boots, but it's not you.
-
Everyone in Los Angeles Knows This Shoe Trend Makes Denim Shorts Look Way Cooler
Denim shorts never looked so good.
-
Shop 31 of This Week's Best New Arrivals
Buckle up.
-
I Went to Shop the Zara Sale But Got Distracted by These 27 New-In Buys and Never Looked Back
They are too good.
-
Spotted at Wimbledon: The Anti-Summer Shoe Trend You Don't Usually See in the Stands
Never too hot for these.
-
I'm Bored With My Closet—These 33 Chic Nordstrom Pieces Have the Power to Turn Things Around
Effortless and expensive looking is the vibe.
-
I Just Got Back From NYC, and Now, I Want to Order These 7 Trends From Reformation
My cart is very full.
-
Believe Me—You'll Still Want These 36 Items in 2026 (and '27 and '28)
Timeless with a capital T.