I hit the mother lode of stylish waterproof boots that are also insanely comfortable. I ordered almost all of the boots on this list for a particular client and I’ve never had so much trouble editing down a shopping session to just a few options. Every single pair of boots I showed my client was gorgeous, waterproof, and hysterically comfortable. I used the word hysterical because that is how I feel about the awesomeness of these stylish waterproof booties.
Blondo Valli 2.0 Waterproof Bootie
As I mentioned in my fall essentials post, tan booties and rain booties are two must-haves for the season. And these Blondo Valli 2.0 Waterproof Booties check off both boxes at the same time! You know I love efficiency.
Cougar Kensington Rain Boot
You might recognize the Cougar Kensington Rain Boot from my post on the 5 Stylish Walking Shoes that I took to Europe. It comes in a slew of colors, but I recommend crimson (pictured above) and walnut as the two most scrumptious options. It’s available at Nordstrom, DSW, Amazon, and Zappos.
Bos. & Co. Reveal Waterproof Bootie
Jeffrey Campbell Clima Rain Bootie
The Jeffrey Campbell Clima Rain Bootie is another wonderful option at a very wonderful price point.
Sorel Cate Lace Rogue Boots
You know I’m loving lace-up booties, aka combat boots, this fall. The heel on the Sorel Cate Lace Rogue Boots gives a feminine twist to these otherwise rugged boots. They’re available at Shopbop, Zappos, Sorel, and Nordstrom.
Blondo Sassy Waterproof Bootie
Stand out with these fabulous leopard print booties. The Blondo Sassy Waterproof Booties are made of a soft fabric that is, of course, waterproof. These boots are available at Nordstrom, Zappos, and Amazon.
FitFlop Skandi Leather Ankle Boots
I wore these FitFlop Skandi Leather Ankle Boots all over the glorious city of Chicago. You will love the side zipper on these boots. You’ll appear detail-oriented and not lazy, and only you, I, and those with a good view of your inner ankle will know the truth (wink). You basically never have to tie your shoes, but you will look as if you did.
Sizing Tip: These run huge! Order a whole size down. If you are an 8, you are a 7 in these shoes.
Joules Rainwell Short Height Slip On Rain Boots
I love Joules’ sneaker take on the classic rainboot. The Joules Rainwell Short Height Slip On Rain Boots will definitely keep your feet dry. These boots are available at Joules, Nordstrom, and Zappos.
Bos. & Co. Womens Risk Chelsea Boot
This Bos. & Co. Womens Risk Chelsea Boot is the stylish waterproof boot that my client kept. It ended up being the most comfortable of them all. Plus, the color and style of the shoe is the most versatile for the rain-friendly wardrobe we created for her.
These Toms Mesa boots are one of my favorite pairs of stylish waterproof boots. I dream of being a lady lumberjack, and these boots are my fairy godmother.
Blondo Helen Waterproof Hiker Boot
The Blondo Helen Waterproof Hiker Boots have a zipper on the side so you can take them on and off without fussing over all the laces.
Blondo Que Waterproof Bootie
Dr. Scholl’s So Cozy Waterproof Bootie
These hiker-inspired wedge boots are insanely comfortable. I love the plaid laces and faux-shearling lining on the Dr. Scholl’s So Cozy Waterproof Bootie. These booties are available at Nordstrom, Zappos, and Amazon.
Aquatalia Denisse Block Heel Bootie
I adore these sleek, black suede booties. The Aquatalia Denisse Block Heel Booties have an inner zipper, making them easy to put on and a textured sole that will keep you from slipping on rainy days. These boots are available at Nordstrom, Bloomingdale’s, Saks 5th Avenue, and Zappos.
Ugg Emmeth Waterproof Chelsea Boot
Vince Henderson Weatherproof Chelsea Boot
The chunk heel gives a utilitarian vibe to these Vince Henderson Weatherproof Chelsea Boots.
La Canadienne Joanie Waterproof Bootie
Italian suede?! An inner zipper?! And they’re waterproof?! These La Canadienne Joanie Waterproof Booties have it all.
Joules Rainwell Short Height Rain Boots
I just learned about Joules at Altitude Summit and I am in love. It is the most stylish line of rain boots I have seen. These Joules Rainwell Short Height Rain Boots are just delicious. Pair them with light wash cuffed blue jeans, or a cuffed casual pant. These boots are available at Joules and Amazon.
Blondo Rachael Waterproof Bootie
I adore these Blondo Rachael Waterproof Booties, but they are most versatile with a pale color palette. Like all the boots on this list, they are wonderfully comfortable. These also have that glorious side zipper on the inner ankle so you don’t have to worry about tying your shoes. They are available at Amazon, Nordstrom, and Macy’s.
Børn Cove Waterproof Chelsea Boot
Joules Ashby Lace Up Rain Boots
These Joules Ashby Lace Up Rain Boots also fulfill my lady lumberjack dreams. Pair them with earth tone leggings, olive green skinny cargo pants, or cuffed jeans to create your own chic lumberjack look. Note, you will have to actually tie your shoes with these if you can’t slip them on and off your feet.
Blondo Ramona Waterproof Lace-Up Boot
This Blondo Ramona Waterproof Lace-Up Boot is practically sexy with its compact silhouette and perfect details. Pair it with the Two by Vince Camuto black leggings for a sleek rainy day look. Notice it doesn’t have a side zipper, which means you will have to tie your shoelaces.