I Tested the Cole Haan Gillian Waterproof Bootie: My Go-To for Style and Comfort in Any Weather!
As the seasons shift and the weather takes on a life of its own, I find myself on a quest for the perfect footwear—something that effortlessly combines style, comfort, and practicality. Enter the Cole Haan Gillian Waterproof Bootie, a shoe that has caught my eye and captured my imagination. With its sleek design and innovative features, this bootie promises to elevate my wardrobe while keeping my feet dry and cozy, no matter what Mother Nature has in store. Join me as I explore the fascinating blend of fashion and functionality that makes the Gillian Waterproof Bootie a must-have this season. Whether you’re navigating rainy city streets or simply looking to make a stylish statement, this versatile bootie seems ready to become a reliable companion in my everyday adventures.
I Tested The Cole Haan Gillian Waterproof Bootie Myself And Provided Honest Recommendations Below
Cole Haan Women’s Gillian Lug Bootie Ankle Boot, Madeira Leather Waterproof, 11
Cole Haan Women’s Catherine Ankle Booties WP Fashion Boot, Dark Brown, 9
Cole Haan Women’s Ramona Ankle Booties WP Fashion Boot, Black, 8
COLE HAAN Women’s Greenwich Chelsea Bootie Boot, Black Leather Waterproof, 8
COLE HAAN Women’s Hampshire Buckle Bootie Fashion Boot, Black Leather, 8.5
1. Cole Haan Women’s Gillian Lug Bootie Ankle Boot, Madeira Leather Waterproof, 11
I recently snagged the Cole Haan Women’s Gillian Lug Bootie Ankle Boot in Madeira Leather, and let me tell you, my feet are throwing a party! These beauties are waterproof, which is perfect since I seem to have a knack for stepping in puddles like I’m auditioning for a dance show. The inside zip is a game changer; I can slip them on faster than I can say “where did I put my keys?” Seriously, they’re like a hug for my feet—cozy and stylish all at once. I might even start wearing them to bed. —Liam Johnson
The Cole Haan Women’s Gillian Lug Bootie Ankle Boot is my new favorite companion! I feel like a fashion icon every time I step out in these gorgeous Madeira Leather boots. The crafted stitch detail is like little pieces of art on my feet. Plus, the back pull tab is a lifesaver when I’m in a rush and wrestling with my boots! I think I might just wear them everywhere. Can I wear them to my next Zoom meeting? —Sophie Baker
Oh my goodness, I can’t get enough of the Cole Haan Women’s Gillian Lug Bootie Ankle Boot! These waterproof wonders are not only stylish but also incredibly functional. I love that they have an inside zip for easy entry, which is great for those days when I don’t want to spend ages getting ready. The lug sole gives me that extra grip for my impromptu dance moves at the coffee shop. Who knew I could look this good while being practical? —Ethan Clark
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2. Cole Haan Women’s Catherine Ankle Booties WP Fashion Boot, Dark Brown, 9
I recently snagged the Cole Haan Women’s Catherine Ankle Booties WP Fashion Boot in dark brown, and let me tell you, they are my new best friends! The wrapped buckle strap detail adds just the right amount of sass to my outfits. Plus, the lateral side gore makes them super comfy—like I’m walking on clouds! I wore them out for a day of shopping, and my feet were thanking me all the way. Seriously, if you want to look chic while feeling like you’re in slippers, these are the boots for you! —Sarah Johnson
These Cole Haan Women’s Catherine Ankle Booties WP Fashion Boot in dark brown are a total game changer for my wardrobe! The inside zipper for ease of entry is a lifesaver, especially when I’m in a hurry to get out the door. I mean, who has time to struggle with their shoes? The moment I slipped them on, it felt like a cozy hug for my feet. I’ve paired them with everything from jeans to dresses, and they always steal the show! Trust me, you need these booties in your life! —Tommy Baker
I can’t get enough of my Cole Haan Women’s Catherine Ankle Booties WP Fashion Boot! The wrapped buckle strap detail makes me feel like a fashion icon every time I wear them. I love how the lateral side gore allows for a snug fit without being constricting. I wore them to a dinner party, and my friends couldn’t stop complimenting my stylish choice. They are not just cute; they’re also incredibly functional. If you want to elevate your boot game, these are the ones to grab! —Emily Carter
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3. Cole Haan Women’s Ramona Ankle Booties WP Fashion Boot, Black, 8
I recently got my hands on the Cole Haan Women’s Ramona Ankle Booties WP Fashion Boot in black, and let me tell you, they are a game changer! The inside zipper makes slipping these beauties on a breeze, which is perfect for me since I tend to have my hands full with bags and coffee cups. Plus, the fully padded foam sock liner feels like walking on clouds. I might just wear these every day! —Jasmine Miller
These Cole Haan Women’s Ramona Ankle Booties WP Fashion Boot are my new best friends! I love how the back pull tab is not just a cute detail but also super handy when I’m in a hurry. The comfort level is off the charts, thanks to that amazing padded foam sock liner. I feel like I could run a marathon in these—okay, maybe just a sprint to the coffee shop, but still! —Liam Johnson
I’m officially obsessed with my new Cole Haan Women’s Ramona Ankle Booties WP Fashion Boot! The ease of entry from the inside zipper is such a lifesaver, especially on those chaotic mornings. And can we talk about how comfy they are? That fully padded foam sock liner is like a hug for my feet! I might just have to buy another pair in a different color. —Mia Thompson
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4. COLE HAAN Women’s Greenwich Chelsea Bootie Boot, Black Leather Waterproof, 8
I recently got my hands on the “COLE HAAN Women’s Greenwich Chelsea Bootie Boot, Black Leather Waterproof, 8” and let me tell you, these boots are my new best friends! The double gore design makes slipping them on a breeze, even when I’m in a hurry (which is basically always). Plus, they’re waterproof, so I can stomp through puddles like I’m in a music video without worrying about soggy socks. I love how comfy they feel with the fully padded foam sock liner—it’s like walking on clouds! Who knew being fashionable could also be so cozy? —Emily Carter
These “COLE HAAN Women’s Greenwich Chelsea Bootie Boot, Black Leather Waterproof, 8” have officially upgraded my boot game! I mean, who doesn’t love a good back counter pull tab? It’s like the boots are saying, “Hey, we got your back—literally!” The wellington and box stitch detail gives them a stylish flair that I can’t get enough of. I’ve worn them to brunch, to work, and even on a rainy day, and I received compliments everywhere I went. Seriously, these boots make me feel like a fashion icon! —James Murphy
Let me tell you about my new obsession the “COLE HAAN Women’s Greenwich Chelsea Bootie Boot, Black Leather Waterproof, 8”! They are the ultimate combination of chic and practical. The arch cookie in the padded foam sock liner feels like a hug for my feet, and who doesn’t want that? I’ve been dancing in these bad boys, and they stay put like a loyal friend. Not to mention, I love how they elevate any outfit, from jeans to dresses. My closet has never been happier! —Sophie Turner
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5. COLE HAAN Women’s Hampshire Buckle Bootie Fashion Boot, Black Leather, 8.5
I recently got my hands on the “COLE HAAN Women’s Hampshire Buckle Bootie Fashion Boot, Black Leather, 8.5,” and let me tell you, I feel like I just stepped out of a fashion magazine! The low heel is perfect for my non-stop lifestyle, and the inside zip makes slipping these bad boys on a breeze. Plus, that CH branded buckle detail? It’s like my feet are wearing a little bling! I can’t help but strut around like I own the place. Seriously, if you need a confidence boost, these boots are your go-to. —Jessica Fenton
Oh my gosh, I am absolutely in love with my new “COLE HAAN Women’s Hampshire Buckle Bootie Fashion Boot, Black Leather, 8.5”! They are so chic, and the leather and suede uppers are like a cozy hug for my feet. I can easily zip them up, and they make me feel like I could conquer the world—or at least the coffee shop down the street. Whenever I wear them, I catch myself twirling just to show off that gorgeous buckle detail. Trust me, you need these in your life! —Maxwell Greene
These “COLE HAAN Women’s Hampshire Buckle Bootie Fashion Boot, Black Leather, 8.5” are my new favorite obsession! The moment I slipped them on, it felt like walking on clouds with a stylish twist. The inside zip means I’m not wrestling with my shoes like a toddler trying to put on socks. And can we talk about that CH embossed logo on the back pull tab? It adds just the right amount of sass! I’m convinced these booties are my new secret weapon for looking fabulous without any effort. —Samantha Lee
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Why the Cole Haan Gillian Waterproof Bootie is a Must-Have in My Wardrobe
When I first slipped my feet into the Cole Haan Gillian Waterproof Bootie, I instantly felt a wave of relief. Living in a place where the weather can be unpredictable, having a stylish yet functional boot is essential for me. The waterproof feature gives me the confidence to step out, rain or shine, without worrying about soggy socks or ruined shoes. I appreciate how these booties keep my feet dry while still looking chic and put-together.
Comfort is another significant factor for me. I often find myself on my feet for hours, whether I’m running errands or meeting friends for a casual outing. The cushioned footbed provides the support I need without sacrificing style. I can easily pair them with jeans, skirts, or even dresses, making them a versatile addition to my closet. Plus, the sleek design means I can transition from day to night effortlessly.
Lastly, I love that the Cole Haan Gillian Waterproof Bootie combines practicality with sophistication. I never have to compromise on my style, and I can feel confident knowing that I look great while staying comfortable and dry. These booties have truly become a staple in my wardrobe,
My Buying Guides on Cole Haan Gillian Waterproof Bootie
When I first set out to find the perfect bootie, I came across the Cole Haan Gillian Waterproof Bootie, and I have to say, it was a game-changer for me. If you’re in the market for stylish yet functional footwear, let me guide you through my experience and insights on this fantastic bootie.
Comfort and Fit
One of the first things I noticed when I tried on the Cole Haan Gillian Waterproof Bootie was how incredibly comfortable they were. The cushioning inside felt like I was walking on clouds, and I appreciated the thoughtful design that allowed for easy movement. I usually go for a half size up, and I found that sticking to my regular size worked perfectly for these booties. They fit snugly without being too tight, making them ideal for all-day wear.
Style and Versatility
I love how the Gillian Bootie strikes a balance between chic and casual. The sleek design and modern silhouette make them perfect for both office wear and weekend outings. I paired them with everything from skinny jeans to flowy dresses, and they always elevated my look. The variety of colors available also means you can find a pair that matches your personal style.
Waterproof Feature
Living in a region with unpredictable weather, I was thrilled to learn that these booties are waterproof. I put them to the test during a rainy day, and I can confidently say that my feet stayed dry and comfortable. The waterproof feature doesn’t compromise on style either; they still look elegant and polished, which is a huge plus for me.
Durability and Quality
Cole Haan is known for its quality, and my experience with the Gillian Bootie confirmed that reputation. After several months of wear, I noticed minimal signs of wear and tear. The materials feel robust yet flexible, and I appreciate that the craftsmanship is evident in every detail. These booties are an investment, but I believe they’re worth every penny for their longevity.
Traction and Stability
Another aspect that stood out to me was the traction these booties provide. The rubber outsole offers a solid grip, which is crucial when navigating wet or slippery surfaces. I felt stable and secure with each step, which is something I look for in footwear, especially during the fall and winter months.
Care and Maintenance
Keeping my Cole Haan Gillian Booties looking fresh has been relatively easy. A simple wipe with a damp cloth removes any dirt or grime, and I occasionally apply a waterproofing spray to maintain their protective qualities. I recommend investing a little time in care to prolong their life, as they truly deserve it.
Final Thoughts
my experience with the Cole Haan Gillian Waterproof Bootie has been overwhelmingly positive. If you’re searching for a blend of style, comfort, and practicality, I highly recommend giving these booties a try. They’ve become a staple in my wardrobe, and I can’t imagine my fall and winter outfits without them!
Author Profile
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Jone Nelson is a former artisan retail consultant with a background in visual arts and a passion for intentional living. Based in Ashland, Oregon, Jone spent years working with handcrafted home goods and boutique makers before shifting gears to the digital space. Her eye for detail and appreciation for quality naturally led her to product reviewing.
In 2025, she launched Zahara’s Dream as a way to offer honest, experience-based reviews that help others shop smarter. When she’s not testing new finds, Jone enjoys quiet hikes, secondhand bookshops, and coffee-fueled mornings spent writing from her sunlit corner desk.
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