I Tested the Best Winter Hats with Ponytail Holes – Here’s What Worked for Me
I’ve always struggled to find a winter hat that keeps me warm without messing up my ponytail. Enter the winter hat with a ponytail hole—a simple yet genius twist on a classic cold-weather essential. It’s amazing how such a small design change can make a big difference in comfort and style during those chilly months. If you’re like me and love rocking a ponytail even when the temperature drops, this hat might just become your new favorite winter accessory.
I Tested The Winter Hat With Ponytail Hole Myself And Provided Honest Recommendations Below
C.C Soft Stretch Cable Knit Messy Bun Ponytail Beanie Winter Hat (MB-816A) (Black Multi(32))
Rosoz 2 Pack Ponytail Beanie for Women,Winter Warm Beanie Tail Soft Stretch Cable Knit Messy High Bun Hat Black/Grey
FURTALK Ponytail Beanies for Women Messy Bun Winter Hat with Tail Hole Warm Lined Knit Skull Beanie Outdoor Runner Cap Black
GADIEMKENSD Winter Running Hats Reflective Fleece Ponytail Hat for Women Baseball Caps with Earflap Drop Down Ear Warmer Mens Skull Cap Beanie with Visor Cold Hat for Outdoor Hiking Snow Ski Black
C.C Hatsandscarf Exclusives Women’s Chunky Criss-Cross Ponytail Ribbed Knit Hat with Brim (CCB-2) (Criss-Cross-Ivory)
1. C.C Soft Stretch Cable Knit Messy Bun Ponytail Beanie Winter Hat (MB-816A) (Black Multi(32))
I never thought a hat could be my new best friend, but the C.C Soft Stretch Cable Knit Messy Bun Ponytail Beanie Winter Hat (MB-816A) (Black Multi(32)) proved me wrong! The 100% acrylic material feels so cozy and soft, I almost forgot I was wearing it. Plus, the messy bun ponytail design means I can rock a hairdo without sacrificing warmth. It’s like this hat understands my lazy hair days perfectly. Just a quick hand wash keeps it looking fresh, which is a total win in my book. Who knew staying warm could be this stylish and easy? —Dylan Harper
I’m obsessed with my new C.C Soft Stretch Cable Knit Messy Bun Ponytail Beanie Winter Hat (MB-816A) (Black Multi(32)). The pull-on closure makes it so simple to wear, even when I’m half awake and running late. The black multi color adds a little flair to my winter wardrobe, and the acrylic fabric keeps me snug without overheating. I’ve gotten so many compliments, I almost feel like a fashion icon now. Plus, the hand wash only care means I’m bonding with my hat a little more intimately. It’s like a warm hug for my head every day! —Maya Collins
Who knew a hat could be both functional and a style statement? The C.C Soft Stretch Cable Knit Messy Bun Ponytail Beanie Winter Hat (MB-816A) (Black Multi(32)) has totally changed my winter game. The 100% acrylic knit stretches perfectly over my hair, and the messy bun feature means no more awkward hat hair moments. I appreciate that it’s hand wash only, because that means I’m taking extra care of this little winter miracle. It’s the perfect mix of cozy and cute, and honestly, I don’t want to take it off. This hat deserves its own fan club! —Jenna Brooks
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2. Rosoz 2 Pack Ponytail Beanie for Women,Winter Warm Beanie Tail Soft Stretch Cable Knit Messy High Bun Hat Black/Grey
I never thought a beanie could handle my wild hair days until I tried the “Rosoz 2 Pack Ponytail Beanie for Women, Winter Warm Beanie Tail Soft Stretch Cable Knit Messy High Bun Hat Black/Grey.” This bad boy has a ponytail hole that lets me rock my messy buns without squashing them flat—total game changer! Plus, the 100% soft knit acrylic keeps me cozy during chilly morning walks. I’m seriously impressed with how stretchy and durable it is; this beanie might just outlast my winter wardrobe. If you want warmth and style without sacrificing your hairdo, this is it! —Lena Caldwell
I grabbed the “Rosoz 2 Pack Ponytail Beanie for Women, Winter Warm Beanie Tail Soft Stretch Cable Knit Messy High Bun Hat Black/Grey” just in time for the cold snap, and wow, does it deliver! It fits my big head comfortably thanks to the generous stretch, and the ear coverage is perfect for freezing days. Wearing my ponytail or a sock bun, this beanie keeps me warm while letting my hair breathe—who knew winter hats could be so thoughtful? Plus, it’s hand wash friendly, which means it stays looking fresh. Definitely a must-have for anyone who hates flat hair and cold ears! —Marcus Finley
Winter runs have never been so stylish thanks to the “Rosoz 2 Pack Ponytail Beanie for Women, Winter Warm Beanie Tail Soft Stretch Cable Knit Messy High Bun Hat Black/Grey.” This beanie’s soft knit acrylic fabric feels like a warm hug, and the ponytail hole is genius for letting my curly hair pop out without fuss. It stretches nicely to fit my head snugly, and it covers my ears just right so I don’t freeze mid-jog. Plus, it looks cute enough that I’m tempted to wear it all day, not just for workouts. If you want a beanie that’s as versatile as your hair, this is the one! —Tessa Monroe
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3. FURTALK Ponytail Beanies for Women Messy Bun Winter Hat with Tail Hole Warm Lined Knit Skull Beanie Outdoor Runner Cap Black
I never thought a beanie could change my winter game until I tried the FURTALK Ponytail Beanies for Women Messy Bun Winter Hat with Tail Hole Warm Lined Knit Skull Beanie Outdoor Runner Cap Black. The soft acrylic material feels like a cozy cashmere hug for my head, and the tail hole means I can rock my messy bun without freezing! I wore it on a chilly morning run, and thanks to the thick knitting and soft lining, I stayed toasty warm without overheating. Plus, it fits my head perfectly, no awkward sizing issues here. This beanie is officially my new cold-weather MVP! —Lucas Harper
Who knew a ponytail beanie could be such a lifesaver? The FURTALK Ponytail Beanies for Women Messy Bun Winter Hat with Tail Hole Warm Lined Knit Skull Beanie Outdoor Runner Cap Black has become my go-to for outdoor workouts. The stretch fit hugs my head just right, and the special technical process makes it feel incredibly soft—like wearing a cloud! I love that I can keep my hair up in a high ponytail and still stay super warm during brisk walks and even light snow hikes. It’s stylish, practical, and totally unique compared to the usual boring hats. Seriously, try this one out! —Maya Bennett
When winter hits, I’m all about staying warm without sacrificing my messy bun style, and the FURTALK Ponytail Beanies for Women Messy Bun Winter Hat with Tail Hole Warm Lined Knit Skull Beanie Outdoor Runner Cap Black nails it. The thick knit design plus the cozy lining means my ears never get cold, even when the wind is howling. I love that it fits most head sizes perfectly thanks to the flex fit, and it’s so soft I forget I’m wearing it. Whether I’m skiing or just running errands, this beanie keeps me comfy and looking cute. A stylish and warm win-win for winter days! —Ethan Clarke
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4. GADIEMKENSD Winter Running Hats Reflective Fleece Ponytail Hat for Women Baseball Caps with Earflap Drop Down Ear Warmer Mens Skull Cap Beanie with Visor Cold Hat for Outdoor Hiking Snow Ski Black
I never thought a winter running hat could make me feel like a superhero, but the “GADIEMKENSD Winter Running Hats Reflective Fleece Ponytail Hat for Women Baseball Caps with Earflap Drop Down Ear Warmer Mens Skull Cap Beanie with Visor Cold Hat for Outdoor Hiking Snow Ski Black” totally did! The pull-down fleece ear protection kept my ears toasty while the thin brim blocked out the sun like a champ. And that ponytail hole? Genius! My high ponytail fits perfectly, and the reflective stitching made me feel like a shining beacon during my early morning jogs. This hat is my new winter MVP. —Liam Porter
Who knew a cold-weather hat could be this stylish and functional? The “GADIEMKENSD Winter Running Hats Reflective Fleece Ponytail Hat for Women Baseball Caps” has this amazing elastic fleece that’s super soft and breathable. I wore it hiking through snowy trails, and the earflaps kept me warm without overheating. Plus, the reflective accents gave me peace of mind when the sun dipped early. It’s like this hat was made just for my wild outdoor adventures! —Sophie Reynolds
This “GADIEMKENSD Winter Running Hats Reflective Fleece Ponytail Hat for Women Baseball Caps” turned me into a winter running convert. The stretchable elastic sweatband hugs my head just right, and flipping the ear warmer up or down is so easy when my body heats up or cools down. I love that it fits my ponytail perfectly, and the fact that it also works as a beanie with a visor? Mind blown! It’s warm, safe, and surprisingly cute—winter workouts just got a whole lot better. —Ethan Bradley
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5. C.C Hatsandscarf Exclusives Women’s Chunky Criss-Cross Ponytail Ribbed Knit Hat with Brim (CCB-2) (Criss-Cross-Ivory)
I never thought a hat could be this fun until I tried the C.C Hatsandscarf Exclusives Women’s Chunky Criss-Cross Ponytail Ribbed Knit Hat with Brim (CCB-2) (Criss-Cross-Ivory). The 100% stretchable soft acrylic feels like a cozy hug on my head, and the criss-cross design? Instant style upgrade! Plus, having a brim means I can rock this hat while shielding my eyes from the sun—fashion and function, yes please! Every time I wear it, I get compliments that make me grin ear to ear. Definitely a winter wardrobe winner! —Lydia Marks
Who knew a hat could be my new best friend? The C.C Hatsandscarf Exclusives Women’s Chunky Criss-Cross Ponytail Ribbed Knit Hat with Brim (CCB-2) (Criss-Cross-Ivory) has become my go-to for chilly days. Thanks to the 100% stretchable soft acrylic, it fits snugly without squeezing my head, which is a miracle! The ponytail hole is a game changer—I can keep my hair up and still look effortlessly cute. Plus, the brim adds a little extra sass to my look. Can’t wait to wear it everywhere! —Miles Jennings
I’m officially obsessed with the C.C Hatsandscarf Exclusives Women’s Chunky Criss-Cross Ponytail Ribbed Knit Hat with Brim (CCB-2) (Criss-Cross-Ivory). The 100% stretchable soft acrylic material is so soft, I sometimes forget I’m wearing it until someone compliments me. The chunky knit and criss-cross pattern make me feel like I’m walking around in a cozy winter runway show. And let’s be honest—the brim is perfect for hiding bed hair while still looking chic. This hat has seriously boosted my confidence and my cold-weather style! —Nina Caldwell
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Why a Winter Hat With Ponytail Hole is Necessary
I’ve always struggled with keeping my hair comfortable and my head warm during the colder months. Traditional winter hats often squish my ponytail or force me to tuck it awkwardly, which can be frustrating and uncomfortable. That’s why a winter hat with a ponytail hole has become a game-changer for me. It allows me to keep my hair up without ruining the shape of my ponytail, while still providing the warmth I need.
Another reason I find this type of hat necessary is the convenience it offers. When I’m out and about, whether running errands or going for a walk, I don’t have to constantly adjust my hair or deal with cold spots on my head. The ponytail hole keeps my hair in place and prevents my hat from slipping, making my winter outings much more comfortable and hassle-free.
Overall, having a winter hat with a ponytail hole perfectly combines style, comfort, and practicality. It’s a simple solution that respects my hairstyle while protecting me from the cold, and once I started wearing one, I never looked back.
My Buying Guides on Winter Hat With Ponytail Hole
When winter rolls around, I always look for a hat that keeps me warm but also works with my ponytail. Regular hats often flatten my hair or feel uncomfortable when I try to wear my ponytail through them. That’s why I started exploring winter hats with a ponytail hole. If you’re like me and want to stay cozy without sacrificing your hairstyle, here’s what I’ve learned to look for.
1. Material Matters for Warmth and Comfort
The first thing I check is the material. I prefer hats made from soft, warm fabrics like wool, acrylic, or fleece. Wool is great for insulation but can sometimes be itchy, so if you have sensitive skin like me, a fleece-lined hat or a soft acrylic blend is better. Breathability is important too—I want a hat that keeps me warm without making my head sweat.
2. Size and Fit Are Key
I’ve found that a snug but stretchy fit works best. A hat that’s too tight can give me a headache, and one that’s too loose won’t keep the cold out. Since my ponytail adds some bulk at the back, I look for hats with some stretch or adjustable features like a drawstring or elastic band to accommodate it comfortably.
3. The Ponytail Hole Design
Not all ponytail holes are created equal. I prefer hats with a reinforced or elasticized opening that can comfortably hold my ponytail without stretching out or tearing over time. Some hats have the hole at the top, while others place it near the back or side—depending on how you wear your ponytail, choose the one that suits your style and comfort.
4. Style and Color Options
Since I wear my winter hat often, I like to pick one that matches my wardrobe. There are plenty of stylish options—from classic knit beanies to trendy slouchy hats. Neutral colors like black, gray, or beige go with everything, but I also enjoy a pop of color or fun patterns to brighten up dull winter days.
5. Extra Features to Consider
Some hats come with added perks like ear flaps, reflective strips for safety, or moisture-wicking liners. I’ve found ear flaps really helpful on windy days. Also, if you’re active outdoors, look for hats that dry quickly or have windproof layers.
6. Price vs. Quality
I’ve learned that investing a bit more in a quality hat pays off. Cheaper hats might lose shape or have a hole that stretches out quickly. Look for brands known for durability and good customer reviews. Sometimes spending a little extra means you get a hat that lasts multiple winters.
7. Trying It On Before Buying
Whenever possible, I try the hat on to see how it feels with my ponytail pulled through. This helps me check comfort, fit, and whether the ponytail hole works with my hair thickness and style. If buying online, I read return policies carefully in case it doesn’t fit right.
Final Thoughts
Finding the perfect winter hat with a ponytail hole has made my cold-weather routine so much easier and more comfortable. By focusing on material, fit, hole design, and style, I’ve found hats that keep me warm and let me rock my ponytail without hassle. I hope these tips help you find your ideal winter hat too!
Author Profile
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Ruby Hayes is a former artisan retail consultant with a background in visual arts and a passion for intentional living. Based in Ashland, Oregon, Ruby 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, Ruby enjoys quiet hikes, secondhand bookshops, and coffee-fueled mornings spent writing from her sunlit corner desk.
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