1. Hunter Original Chelsea Insulated Boot ($149.99)
These insulated boots will not only keep your feet protected from any inclement weather, but also make sure you stay warm! These ankle, heeled shoes feature a synthetic outsole, removable insole, a trendy round sole silhouette and pull-on closure with elastic panels. What's not to love?
2. Hunter Original Short ($127.96)
Need a durable—but still aesthetically pleasing— pair of rainboots? We've got you covered with this mid-calf-length set, also from trusted brand Hunter. These boots are certified vegan, feature vulcanized natural rubber construction and a multi-layer cushioned sponge insole. In addition, your new fave boots also have quick dry woven nylon lining.
3. Vessi Weekend Chelsea Boots Women ($140)
A waterproof pair of Chelsea boots is the perfect addition to any winter closet, and these kicks from Vessi resemble a comfy pair of sneakers with added protection for your feet. According to the label, they are crafted with a "lightweight, breathable knit," and they also boast an entirely vegan, non-skid rubber outer sole.
4. Sperry Cutwater Deck Boot ($94.95)
Whether you're going hiking, boating, or trudging through the snow, these Sperry boots are made with perforated neoprene, which dries quickly when wet, and provides added ventilation. The rubber outsole on each shoe also has the label's signature razor-cut design and uses technology that is made for "ultimate wet/dry traction."
5. Everlane The Rain Boot ($85)
These ankle rainboots are so cute that you'll want to wear them even on a sunny day! As noted by the label, this pair's stretch side panels and pull tabs make it "easy to slide on and go," and they also "leave plenty of room for thick, comfy socks" if you want to brave a winter storm (and still look stylish all the while) in them.
6. Bogs Sweetpea Boots ($84.94)
This practical pair of waterproof boots from Bogs stand out as they feature DuraFresh® bio-technology that "activates to fight unwanted odors," as the brand notes, plus they're super sleek! These rain-proof shoes also have side gore panels and a back pull loop for easy on and off access, and they also offer a comfy cushioned textile footbed.
7. Vionic Karsen Boots ($74.99)
A chunky pair of leather boots can add instant oomph to any ensemble, and this pair from Vionic also has waterproof zippers. To keep you safe from mud and muck, these shoes also have seam-sealed technology which effectively keeps moisture out.
8. SOREL Chelsea Boots ($122.98)
Chelsea boots are always a great option to pair with dresses or jeans, and this high quality pair from Sorel has waterproof coverage you need along with the timeless shape you're after. With "plush EVA cushioning and a molded rubber sole," as the label points out, this is one pair of booties that are made to last long.
9. Asgard Women's Ankle Rain Boots Waterproof Chelsea Boots ( $32.99)
With a price that can't be beat and countless positive reviews, these waterproof Chelsea boots are definitely worth checking out! If you want boots with an enduring matte finish, a roomy area for your toes, and an EVA foam insole for comfort as you walk, this just might be the pair for you.
10. Blondo Women's Villa Waterproof Ankle Bootie ($129.74)
If you're searching for a pair of ankle boots that look less like *actual rain boots* compared to the others on this list, look no further. These booties may feature waterproof suede and leather, but you'd never know! They also have a low, stacked heel and textured rubber sole for better traction. Yes please!
11. SOREL Joan of Artic Wedge ($200)
A wedge is the perfect in-between choice if you aren't in the mood to wear heels, platforms or completely flat boots. These wedged booties from Sorel are made with waterproof full-grain leather to help you stay stylish and equipped for all kinds of weather conditions.
12. UGG Simmens Motorcycle Bootie ($109.98)
It's 2023, and UGGs are back and better than ever! This nostalgic yet modern pair features edgy buckles, a rounded toe shape, delicate, ultra-subtle metallic detailing at the top panel, and of course— the essentials— a waterproof leather upper and inside zip closure.
13. UGG Women's Bonham III Ankle Boot ($90.81)
Can't get enough of the UGGs return? We can't either. We love this pair of waterproof leather ankle boots from the brand that are made with water repellent materials and also contain wool lining and a wool insole to keep you toasty warm for longer.
14. Sperry Saltwater Quilted Nylon ($66)
This quintessential rainboot offers you a water-resistant rubber shell, barrel-tied rawhide lacing and zipper that makes the fit as secure as can be. Another plus of these Sperries is that they feature rust-proof eyelets, a protective rubber duck shell and waterproof quilted nylon shaft. Cute, comfy and practical! (Oh, and did we mention affordable, too?)
15. Blundstone BL558 Classic 550 Chelsea Boot ($219.95)
We'll close our list with a pair of waterproof Chelsea boots that are as polished and professional-looking as they are comfortable. These Blundstone ankle boots are equal parts rockstar-esque and weatherproof. Made with dual-density thermopolyurethane outsoles, these shoes are not only great for any weather climate, but they are also lightweight and easy to slip on and off.