The Best Stylish Rain Boots to Brighten Up Even the Dreariest of Days

You might even look forward to the next time showers are in the forecast with these adorable boots.

We found the most stylish boots to wear on those dour rainy days. Julia Cherruault for Observer

It’s not always easy to come up with a stylish ensemble on those days when a torrential downpour (or even just a drizzle, to be honest) is imminent, and we think that’s largely because rain boots so often feel like the least fashionable footwear. Just because there’s rain in the forecast doesn’t mean you have to give up on finding a chic outfit, though, and that includes your choice of shoe.

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Keeping your feet warm, dry and comfortable is of the utmost importance, of course, but luckily we’ve found all the best rain shoes that are just as stylish as they are practical for the dreariest of rainy days. Below, see our favorite waterproof boots to elevate your rainy day look—you might even look forward to splashing around in puddles.

Stutterheim. Courtesy Stutterheim

Stutterheim Chelsea Rainwalker

The Swedish brand is known for its waterproof coats and shoes, like these stylish Chelsea booties. We love the cream shade as an alternative to the expected black colorway, and the lug sole is both very on-trend as well as extremely practical for keeping your feet away from the murky streets. $165, Stutterheim.


Bernardo Andra Rain Boot

Those of us who can’t get enough of combat boots will love these lace-up shoes to elevate your inclement weather aesthetic. They’re also great for days when you’re not sure if the rain will actually start pouring down on you, as you could easily wear them even sans showers. $198, Bernardo.

Hunter Boots. Courtesy Nordstrom.

Hunter Refined High Gloss Quilted Short Waterproof Rain Boot

We’re longtime fans of Hunter rain boots, which are so durable and chic. They’re definitely worth the investment, and aside from the brand’s go-to knee-high wellies, we’re also very into this glossy patent leather mid-calf style, with perfectly preppy quilted detailing. $165, Nordstrom.

Chloé. Courtesy Net-a-Porter

Chloé Betty Rubber Boots

These stylish rubber boots work with just about any outfit, and look just as appropriate during rainy weather as on the sunniest of days. $495, Net-a-Porter.

Yoox. Courtesy Yoox

8 By Yoox Rubber High Rain Boots

You can’t go wrong with a classic knee-high rain boot, and this monochrome ivory style is practical while still stylish. $60, Yoox.

Boden. Courtesy Boden

Boden Bamburgh Wellington Boots

Bring a cheerful rainbow of color to dour days with these adorable rain booties. $80, Boden.

Sperry. Courtesy Sperry

Sperry Saltwater Wool Embossed Duck Boot With Thinsulate

A navy moment is an always-chic alternative to basic black, and these lace-up duck boots feature wool lining on top for a cozier aesthetic. $71.99, Sperry.

Everlane. Courtesy Everlane

Everlane The Rain Boot

A simple black Chelsea rain boot is a wardrobe staple. $75, Everlane.

Moncler. Courtesy Nordstrom.

Moncler Ginette Logo Waterproof Rain Boot

If you want to splurge on your rainy weather apparel, consider this glossy lug sole ankle boot. The shoe is lined with jersey, to keep your feet warm and dry. $395, Nordstrom.

ModCloth. Courtesy ModCloth

Joules It’s Raining Cats and Dogs Rain Boot

It’s impossible not to smile when you’re wearing these adorable rain boots, emblazoned with cats and dogs because, well, you know the saying. $80, ModCloth.

Burberry. Courtesy Nordstrom

Burberry Flinton Check Waterproof Rain Boot

A Burberry trench is one of the chicest rainy day looks out there, but don’t forget the British brand also makes footwear, too. These are perfect for the next time showers are in the forest, and we love the little peek of the signature Burberry tartan plaid. $320, Nordstrom.

Dr. Scholls. Courtesy Dr. Scholls

Dr. Scholls Fireside Waterproof Block Heel Bootie

We love that these waterproof shoes are totally sustainable, and they’re perfect for those that just don’t want to give up a chunky heel, even during unpleasant weather conditions. $150, Dr. Scholls.

Ugg. Courtesy Ugg

Ugg Classic Clear Mini Rain boot

One of our biggest issues with rain boots is that they aren’t always especially warm, as even when they keep our feet dry, they don’t block the chill. That’s all fixed with these Uggs, which feature the brand’s signature cozy lining on the inside and waterproof materials on the outside. $150, Ugg. The Best Stylish Rain Boots to Brighten Up Even the Dreariest of Days