20 Best Waterproof Boots That Won’t Ruin Your Outfit 2021 — Stylish Water-Resistant Boots

Raise your hand if you’ve ever felt personally victimized by a heavy rain forecast (you can’t see me right now, but I have both hands raised). The amount of dread I get when it’s pouring out and I actually have to go somewhere is unprecedented. Not only because the weather is gross, but also because I don’t like looking not cute, and stylish waterproof boots aren’t exactly easy to come by—or so I thought.

I’ve spent a lot of time on this earth searching for the best waterproof boots around—because that is just how passionate I am about this cause—and today, I am here to share with you my findings. From a pair of cult-favorite rain boots to water-resistant winter boots to even heeled booties made of waterproof suede—you can find ’em all, below.

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This cult-favorite

The Rain Boot



Slip-resistant, super comfy, and easy to slip on. Of course, these are a best-seller.


this equestrian-inspired pair

Carden Waterproof Knee High Boot



Forget what you thought you knew about weather-resistant boots. Waterproof does not equal clunky. And this sleek riding boot is proof.


This heeled bb

Henderson Weatherproof Chelsea Boot



Hi, I think I’ve fallen in love and I can’t get back up. These heeled boots are exactly what my winter wardrobe needs.


this luxe option

Alps Boot

Brother Vellies


I know the price is pretty up there. But if you’re open to a designer boot, it’d be smart to go for one that’s at least water-resistant, no? Also, these are just too cute to pass up (even if my bank account is telling me no).


this OG rainboot

Original Tall Waterproof Rain Boot



I couldn’t not include a pair of Hunter wellies. These classic boots are a staple for any waterproof wardrobe.


these namedropping boots

Rain Boot



Big fan of the logomania trend? These high-gloss boots are just right for you.


these tall leather boots

Florence Waterproof Over the Knee Boot



Get you a pair of OTK boots made of waterproof leather—trust me. They’re worthy of the investment.


these lace-up snow boots

Leather-trimmed suede and shearling ankle boots

See By Chloé


Calling it now: Snow boots are in. And if you’re looking for something to wear aprés-ski, I think I just found the perfect ones for ya.


This affordable option

Khaki PU Cleated Sole Chunky Rain Boots



At just under $60, these chunky rain boots are a steal.


this goes-with-everything boot

Laguna Waterproof Chelsea Boot



Take my professional advice and grab you a pair of waterproof Chelsea boots that’ll go with just about anything in your closet.


this posh boot

Michela SP Weatherproof Genuine Shearling Lined Boot



If you’re looking for a waterproof boot that’s a bit more polished, then go for this sleek one.


this super flattering pair

Khaki Chunky Cleated Sole Calf High Chelsea Boots



The OG Chelsea boot gets an update with this pair. Peep that extra chunky lug sole and elongated shaft. You probably wouldn’t guess so, but it makes for a flattering fit.


these shearling snow boots

Curly Rock Shearling Sneaker Boots



Hey, go big or go home, right? These shearling “sneaker boots” may be pretty ornate, but they’re also just really chic? 


this v comfortable contender

Kensington Chelsea Rain Boot



Looking for something with cushy arch support? Then get a load of these guys.


This monochromatic one

Cloudy Waterproof Chelsea Rain Boot



For those who love monochromatic anything, here’s a splash-proof pair of boots that’s rendered in a muted olive tone.


these super snow boots

Shell and faux leather snow boots

Moon Boot


Moon Boot is the brand to shop if you’re looking for the perfect pair of snow boots. Whether you’re aprés-skiing or just gearing up for the next big snowmageddon, you gotta at least add these to your cart. 


these micro wellies

Original Waterproof Chelsea Rain Boot



Why, yes, Hunter does make their iconic rain boots in mini form. Pull on a pair of these short cuties if you’re not into that whole high-knee boot thing.


these no-fuss booties

Tinsley Waterproof Rain Boot



Hi, these are your new go-to rain boots (just look at that super sleek design). OK, bye.


these fuzzy boots

Joan of Arctic™ Next Lite

No cold toes with these boots. The water-resistant shearling and splash-proof upper will make sure of that.


this bougie pair

For Riding Wellington Boot



For the designer-loving sneakerhead who’s in the market for a new pair of wellies.

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10 thoughts on “20 Best Waterproof Boots That Won’t Ruin Your Outfit 2021 — Stylish Water-Resistant Boots

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