The 17 Best Rain Boots to Keep Your Feet Dry (and Your Outfit On-Point)

You wake up, it’s pouring rain, and you need to go to work. It’s time, again, to make a call. Choose your own adventure: Do you a) wear your normal work shoes, try to avoid puddles, fail, and probably ruin their leather, b) wear sneakers and spend the rest of the day trying to distract yourself from your soaking wet socks, c) wear big, heavy rain boots and spend the day squeaking around the office/sweating to death inside of them at your desk, or d) invest in a pair of waterproof, Esquire-approved rain boots that’ll look good and save you from all of the previously listed miserable scenarios? Pretty easy choice. Here are our 17 favorite rainproof shoes and boots to save you from the rainy-day footwear conundrum.

Rubber Chelsea Rain Boots



If you’re combing the internet for a good ol’ pair of classic rubber rain boots, go for a subtle, black, Chelsea style. This Amazon pick is easy and affordable. 

Chuck Taylor Nubuck Boot



If you’re a very strict sneaker wearer, waterproof high-top Chuck Taylors are your best rainy-day bet. 

Gen Waterproof Rain Boot

Kenneth Cole


Kenneth Cole makes a solid, reliable option for when it’s really coming down. Plus, a little party on the inside. 

Winter Gore-Tex Chuck Taylor All Star



This winterized option from Converse is lined with polar fleece and protected by Gore-Tex, so you can get away with avoiding boots no matter how cold or wet it is outside. 

Stormers 6″ Steel Toe Work Boot



Whether you work outdoors with heavy objects or you are prone to dropping your laptop on your toes (in the rain? Who are we to judge?), CAT’s steel toe rubber work boot is the way to go for heavy-duty rain wear.  

Kenny Waterproof Oxford



These waterproof Oxfords from Blondo won’t keep your ankles dry, but for a wet workday, these are a great option for the office. 

Grayson Waterproof Chukka Boot

Nordstrom Men’s Shop


Suede chukkas? For a rainy day? Well, actually…yeah. These waterproof ones from Nordstrom’s in-house men’s shop don’t look like rain boots, but then again, that’s the whole point.

Original Short Waterproof Boot



You can’t beat a classic. And when it comes to rain boots, it doesn’t get more classic than Hunter.

Grant Waterproof Chelsea Boot



Blondo is a Canadian brand that knows how to make serious weatherproof footwear attractive. 

Original Waterproof Chelsea Boot



Hunter is the king of rain boots (or more accurately, the Queen: the brand holds two Royal Warrants of Appointment to Her Majesty The Queen and HRH The Duke of Edinburgh). If classic wellies aren’t your thing, maybe a low-key Chelsea is. Puddle jump like royalty. 

Neumel Waterproof Chukka Boot



These chukka boots from Ugg are cozy and comfy (and waterproof!). Perfect for a casual run to the store for rainy-day movie snacks. 

BL500 Boot



Blundstones aren’t technically waterproof, but ask anyone who’s worn a pair on a rainy day (or stepped ankle-deep into a puddle with them on) and they’ll tell you: These are great rain boots. Your feet will stay dry in all but the most ridiculously wet conditions.

Harkland Combat Boot



Ugg’s combat boots are wool-lined, so your feet will stay nice and warm. (And, of course, dry.)

Tor Ultra Hi 2 Waterproof

Hoka One One


For all-weather hiking, go for Hoka One One’s waterproof, extremely comfy outdoor boot.

Wakefield Grand Chelsea Boot

Cole Haan


Cole Haan is downright masterful when it comes to rain boots that don’t look a thing like rain boots. Wear these whenever you want, and rest assured that you’ll always be prepared for an unexpected downpour.

1000 Mile Original Sneaker

Wolverine Heritage


The best type of rain boot is one that looks nothing like a rain boot (but still functions like one, thanks to waterproof Roadmaster leather). 

Renzo Water-Resistant Boot



Aquatalia’s whole thing is high-end, water-resistant footwear. And these Renzo boots fit the bill perfectly. They look great, and they’ll keep your toes comfortable and dry. 

Lauren Kranc is an editorial assistant at Esquire and Masters student at New York University.

Source : Esquire