These 9 Rain Boots Actually Make a Rainy-Day Outfit Chic

I remember when I saw the photos of Kate Moss with Pete Doherty at Glastonbury Festival in 2005. I was still a small child, often fed up with my mom for insisting I wear puffer jackets when it was cold out and rain boots when it poured. I'd try to explain that these practical items were just not cool, and she'd respond by telling me neither was pneumonia.

To me, pneumonia in a leather jacket was better than having someone see me in something practical and pedestrian. Social ostracism felt worse than actual sickness.

And then there were those photos of Kate Moss, which flashed across my computer screen while I was scrolling through Tumblr. She wore a gold knit minidress with a studded belt slung low around her hips, a leather jacket layered on top, a studded bag, and a pair of extremely muddy Hunter rain boots on her feet.

It was one of the coolest looks I'd ever seen, and everyone agreed. The image went viral and still does numbers on the internet whenever people remember its existence. Moss proved that the key to a good outfit was looking like you actually lived in it. She'd look like she was trying too hard if she was wearing anything with a semblance of a heel.

Her opting for the $175 Original Tall Rain Boots by Hunter was cool because it wasn't. She didn't let the boots dictate her whole outfit either. She still accessorized. She still wore the dress. Adding the practical, affordable rain boots took the outfit somewhere you normally wouldn't think to go, and that's peak cool. It's cool to do what others don't think to do and also not care. She wore some riff of this look a handful of times, wearing skimpy, cool pieces with studded accessories and wellies to Glastonbury.

Fellow British style icon Alexa Chung would also become known for her looks at the music festival years later. Instead of dresses, Chung often opted for denim hot pants and striped tees with her Hunter rain boots. They all collectively changed my mind about everything I thought I knew about the shoes my mom would force me to wear.

Because of their necessity in our wardrobes, rain boots are not a trend. They're a true staple, something everyone actually needs. They often pop up on the runway at shows like Burberry, Chanel, and Valentino as a reminder that even high-fashion looks can stand to be humbled with a little rainwear.

Now as an adult, I can admit that—like with most things—my mom was right. Sometimes, I even pull on a pair of rubbery rain boots when it's perfectly sunny and dry because I like the way they add an unexpected texture and a funky feel to my look. I just tell myself it's what Kate Moss would do.

Below, shop the nine pairs of rain boots I'd actually be happy to be seen in.

The Kate Moss–Approved Classic

Why I love them: They're a supermodel-approved classic.

Key details that make them worth it: If they're good enough for Kate Moss, they're good enough for me. Plus, they have puddle-proof rubber, traction-gripping soles, and adjustable buckles. These are the quintessential black rain boots. They're tall and sleek and would look good with anything. Wear them with a dress and a low-riding belt à la Moss or a striped tee and denim shorts à la Chung.

A Close (and Shorter) Second

Why I love them: They're very similar to the tall boots and have a shorter silhouette that helps you unlock new outfit possibilities.

Key details that make them worth it: These waterproof boots have self-cleaning lugged soles, which means you don't have to worry too much about scrubbing off any mud. That sounds like a perfect excuse to fly across the pond for a trip to Glastonbury.

The Viral Staple That's Worth the Hype

Why I love them: The silhouette is so sharp, sleek, and sexy.

Key details that make them worth it: These are the rain boots to get if you want something truly different. They don't even present as rain boots—they just look like really good boots. That's because they are. This pair has gone viral and sold out many times over for being as pretty as it is practical. If you ask any fashion editor about them, they'll either tell you they love them or that they're currently on their wish list.

The Collaboration Worth Grabbing Now

Why I love them: The chunkier shape gives them a bit more edge than most rain boots. They're still rain boots but don't want to take themselves too seriously.

Key details that make them worth it: While still an investment, they're Proenza shoes at a far more accessible price point than what is standard for the high-fashion brand. They also have durable rubber mudguards and a waterproof construction made with comfortable molded midsoles and outsoles. Everything is so deeply thought-out.

The Trendy Shoes That'll Outlast Most Trends

Why I love them: They're Bottega! Seriously, they have now become so associated with Matthieu Blazy's Bottega (RIP) that it's hard not to see them as so much more than rain shoes. They're a reminder that fashion is at its best when there is a bit of whimsy.

Key details that make them worth it: There are so many different iterations of the Puddle style, but these are so easy to just slip into. When the weather is inclement, the last thing you want to be doing is wasting too much time on an outfit that's going to get soaking wet anyway. Also, the colors are fantastic.

The Best Under-$100 Rain Boots

Crocs That Are Runway-Worthy

Why I love them: They work off and on the runway.

Key details that make them worth it: When you think of Crocs, you probably don't think of boots, but that's what Balenciaga is here to do—remind us of all the weird things that fashion can be. These are so different and a instant conversation starter. If you remember the Balenciaga mud show, where models literally walked on a runway made of mud, then you'd trust the brand to know what it's doing with stomping shoes. They're also made with lightweight EVA, so despite being durable, they won't weigh you down.

A Scandi-Girl Staple

Why I love them: Ganni's Chelsea boots are a cornerstone of Copenhagen style. They manage to make every outfit look cool in that elusive, "hard to define but always dreamy" Scandi-girl way.

Key details that make them worth it: I own a tall version of these boots and have worn them into the ground. They will absolutely stand the test of time. They've never failed me, rainy day or not, and always manage to elicit so many compliments from close friends and strangers.

An Old-School Alternative

Why I love them: These are truly timeless and feel retro without feeling outdated.

Key details that make them worth it: These boots are handmade in Morocco by Le Chameau, which has been making the finest rubber boots since 1927. These are handcrafted by a master boot maker, who ensures they're completely leak-free, and have a jersey lining that makes them cozy to slip into.