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As the winter season approaches, it’s time to think about how you can style your hair under those cozy hats without compromising on style. Whether you’re looking for cute ideas for long hair, short hair, or something in between, there are plenty of easy hairstyles that complement your favorite winter hats. From curly hair to sleek buns, we’ve gathered some of the best winter hairstyles you can wear with beanies, berets, and more. Let’s explore 37 trendy winter hat hairstyles to keep you looking fabulous in 2024-2025.
Low Ponytail with Beanie
The low ponytail is a timeless and cute winter look that is perfect for pairing with a beanie. This style suits both long hair and medium hair, providing a chic yet relaxed look. Whether your hair is straight or curly, the low ponytail works wonders by keeping the hair under control while leaving room for your hat to sit comfortably. It’s especially ideal for those who want a hairstyle that works for long hair easy winter looks.
Hair care tip: Use a smoothing serum like the Olaplex No.6 Bond Smoother to control frizz and keep your ponytail sleek throughout the day. If you have curly hair, opt for a curl-enhancing cream like DevaCurl SuperCream for definition.
Loose Waves with Knit Hat
Loose waves combined with a soft, knitted hat create an effortlessly aesthetic look for medium hair or long hair. The gentle texture of the waves contrasts beautifully with the snug fit of the knit hat, making this a go-to style for casual winter outings. The waves give your hair dimension and volume without looking overdone, making it one of the best easy winter looks.
Hair care tip: To keep your waves bouncy and frizz-free, use Moroccanoil Curl Defining Cream before styling. For extra hold, finish with a lightweight hairspray like L’Oréal Elnett Satin.
Side Braid with Beret
A side braid paired with a classic beret is a stylish option for women with long hair who want to add a touch of Parisian flair. This hairstyle not only keeps your hair under control, but it also adds a playful, cute touch to your winter wardrobe. Whether your hair is straight or slightly curly, the side braid works for all textures and face shapes.
Hair care tip: Use a lightweight oil like Ouai Hair Oil to smooth flyaways and add shine to your braid. For those with finer hair, consider using Batiste Dry Shampoo for volume before braiding.
Messy Bun with Wool Cap
The messy bun is a versatile hairstyle perfect for keeping short hair and medium-length hair styled under a wool cap. This look is casual yet aesthetic, making it perfect for both quick errands and relaxed winter weekends. The bun sits high or low depending on your hat style, giving your look a carefree, cute vibe.
Hair care tip: For added volume, spritz your roots with Living Proof Full Dry Volume Blast before gathering your hair into a bun. Use Bumble and Bumble Hairdresser’s Invisible Oil to add moisture and prevent dryness in cold weather.
Straight Hair with Wide-Brim Hat
For a sleek, polished look, straight hair under a wide-brim hat creates a refined winter style. This works especially well for medium-length or long hair and is a great way to frame your face while adding a modern edge to your look. The straight hair contrasts beautifully with the hat’s dramatic brim, giving off an aesthetic vibe perfect for winter.
Hair care tip: To keep your hair smooth and frizz-free, use GHD Heat Protectant Spray before straightening your hair. A shine serum like Paul Mitchell Super Skinny Serum will help maintain that sleek, glossy finish throughout the day.
French Braid with Winter Hat
The French braid is a classic hairstyle that pairs wonderfully with a variety of winter hats. Whether you have long hair or medium hair, the French braid adds a touch of elegance while keeping your hair neatly in place under your favorite winter accessory. This look works particularly well with beanies or wool caps, as the braid’s structure prevents the hat from flattening the hair too much. It’s ideal for creating a polished look without much effort, especially for those chilly days when you want to keep everything looking cute and tidy.
Hair care tip: To make sure your braid stays sleek and frizz-free throughout the day, apply John Frieda Frizz Ease Original Serum before styling. If you have curly hair, enhance the braid’s texture with SheaMoisture Coconut & Hibiscus Curl Enhancing Smoothie for added definition.
Textured Bob with Beanie
A textured bob offers the perfect solution for women with short hair who want to look stylish while wearing a beanie. This cut gives your hair enough body and movement to peek out from under the hat, providing a bit of aesthetic charm to your winter look. This hairstyle is best for those with medium-length or shorter cuts, and it’s an especially easy option for adding flair to casual winter outfits.
Hair care tip: To maintain the texture and volume of your bob, use Oribe Dry Texturizing Spray for a lightweight lift. If you’re styling curly hair, consider using Ouidad Advanced Climate Control Heat & Humidity Gel to keep curls defined without weighing them down.
Sleek Low Bun with Fedora
For those seeking a more refined, elegant winter look, the sleek low bun paired with a fedora is an unbeatable combination. This hairstyle works well for long hair or medium-length hair, offering a sophisticated silhouette that fits perfectly under a fedora without compromising your style. It’s a great option for formal winter occasions or when you want to elevate your everyday look.
Hair care tip: To achieve the sleek finish of this bun, use Redken Shine Flash 02 for added gloss and control. If you have frizzy or coarse hair, consider applying Garnier Fructis Sleek & Shine Anti-Frizz Serum before styling to ensure a smooth result.
Loose Curls with Floppy Hat
Loose curls paired with a floppy hat create an effortlessly stylish and aesthetic winter look that works well for both long hair and medium hair. This is a great option if you’re looking for easy hairstyles to wear with a hat that won’t flatten your curly hair. The loose curls frame your face beautifully while the floppy hat adds an element of bohemian charm, perfect for casual outings or winter get-togethers.
Hair care tip: To keep your curls voluminous and bouncy, use DevaCurl Light Defining Gel to lock in the shape without creating a stiff texture. A lightweight curl refresher like Ouai Curl Crème can also help bring second-day curls back to life.
Fishtail Braid with Newsboy Cap
The fishtail braid is a beautiful and intricate style that adds a touch of sophistication when paired with a newsboy cap. This look is ideal for long hair, especially if you’re aiming for something cute and structured to wear during winter. The fishtail braid allows the texture of your hair to stand out, and the newsboy cap provides a playful, vintage-inspired vibe, making this combination one of the trendiest styles of the season.
Hair care tip: Apply a texturizing spray like Amika Un.Done Volume and Matte Texture Spray before braiding to give the fishtail more grip and volume. If you have curly hair, use a lightweight curl cream like Cantu Curl Activator Cream to smooth and define the strands before styling.
Half-Up Half-Down with Pom-Pom Beanie
The half-up half-down hairstyle paired with a pom-pom beanie is the perfect combination of fun and practicality. This look works well for medium-length or long hair and is particularly flattering for those with curly hair or soft waves. The top section of the hair is pulled up, giving the hairstyle some volume while leaving the lower half free to flow beneath the beanie. This style is both cute and versatile, making it great for winter adventures or casual outings.
Hair care tip: Use a lightweight texturizing spray like Oribe Dry Texturizing Spray on the lower half of your hair to add volume and movement. If you have curly hair, use Mizani True Textures Curl Enhancing Lotion for defined curls that stay frizz-free under the beanie.
Top Knot with Baseball Cap
For a sporty and stylish winter look, the top knot combined with a baseball cap is a go-to choice. This hairstyle works for short hair, medium hair, or long hair, offering a sleek and easy style that keeps hair off your face while adding an athletic vibe. Whether you’re heading out for a winter run or just running errands, this look is both practical and cute.
Hair care tip: Before styling, apply Amika Blockade Heat Defense Serum to protect your hair from heat if you’re using hot tools. To ensure the top knot stays in place, spritz Ouai Matte Pomade for hold and texture without making the hair stiff.
Voluminous Curls with Wool Hat
For those with curly hair, nothing complements a warm wool hat better than big, voluminous curls. This style is perfect for showcasing your hair’s natural texture while keeping it contained beneath a hat. The wool hat adds an element of coziness, while the curls bring in the drama, making this a wonderful option for both long hair and medium-length hair.
Hair care tip: Keep your curls hydrated and bouncy with Moroccanoil Curl Defining Cream to reduce frizz. If you’re dealing with winter dryness, use Briogeo Don’t Despair, Repair! Deep Conditioning Mask to ensure your curls stay soft and moisturized.
Braided Pigtails with Ear Warmer
For a youthful and cute winter look, braided pigtails paired with an ear warmer are the perfect combination. This playful hairstyle works well for both long hair and medium hair, especially if you’re looking for easy ways to keep your hair styled in the winter cold. The braids keep your hair neat and protected, while the ear warmer adds an extra touch of coziness and warmth.
Hair care tip: Before braiding, apply Ouidad Advanced Climate Control Detangling Heat Spray to smooth and protect your hair from winter frizz. For extra hold and shine, finish with Aveda Brilliant Spray-On Shine.
Beach Waves with Bucket Hat
The relaxed vibe of beach waves pairs unexpectedly well with a bucket hat, creating a laid-back yet stylish winter look. This hairstyle works well for those with long hair or medium-length hair who want to achieve an effortlessly aesthetic look even in the colder months. The waves bring texture and movement, while the bucket hat adds a trendy twist that’s perfect for casual winter days.
Hair care tip: To achieve perfect beach waves, use Bumble and Bumble Surf Spray for that lived-in texture. If your hair tends to dry out in winter, use Ouai Wave Spray to keep the waves hydrated and frizz-free.
Side Swept Bangs with Fleece Hat
Side swept bangs are a chic way to wear your hair under a fleece hat during the winter. This hairstyle works particularly well for short hair or medium-length hair, as the bangs frame the face beautifully and peek out just beneath the hat. The soft fleece provides warmth while complementing the gentle curve of the bangs, making this one of the most cute and aesthetic winter looks.
Hair care tip: Keep your bangs in place by using a lightweight hairspray like TRESemmé Compressed Micro Mist Hair Spray for hold without stiffness. For added shine and smoothness, apply CHI Silk Infusion to the lengths and bangs before styling.
Low Braided Bun with Beanie
A low braided bun paired with a snug beanie offers an elegant yet casual winter style that’s perfect for long hair or medium-length hair. This look keeps your hair neatly tucked away while allowing the braid to add texture and sophistication. It’s a practical style for cold weather, ensuring your hair stays in place beneath your winter gear.
Hair care tip: Before braiding, apply Living Proof No Frizz Nourishing Styling Cream to prevent flyaways and keep the bun sleek. Finish with Kenra Platinum Finishing Spray for added hold that lasts throughout the day.
Pixie Cut with Chunky Knit Hat
A pixie cut paired with a chunky knit hat makes for an effortlessly trendy winter look. This style works especially well for those with short hair, as the pixie cut keeps your hair manageable under the hat while still allowing for some volume and texture. The contrast between the short, edgy haircut and the thick knit hat creates an appealing aesthetic perfect for winter fashion.
Hair care tip: Keep your pixie cut looking sharp and textured with American Crew Fiber for hold and volume. If your hair tends to get flat under hats, use Batiste Dry Shampoo to add volume and freshness.
Loose Curls with Fur Hat
Nothing says winter luxury quite like loose curls paired with a statement fur hat. This look works beautifully for long hair and curly hair, allowing the natural volume and texture of your curls to shine while the fur hat adds an element of sophistication. It’s the perfect look for winter outings when you want to feel glamorous yet cozy.
Hair care tip: To keep your curls defined and frizz-free, use Ouidad VitalCurl+ Define & Shine Styling Gel-Cream before styling. A weekly deep conditioning treatment with Moroccanoil Intense Hydrating Mask will help combat winter dryness and keep your curls hydrated.
Side Ponytail with Felt Hat
A side ponytail combined with a sleek felt hat offers a chic and modern winter hairstyle that works for both long hair and medium-length hair. The ponytail is worn to the side, giving a playful and cute vibe, while the felt hat adds structure and elegance. This is a versatile look, perfect for anything from casual winter walks to more formal outings.
Hair care tip: To add shine and smoothness to your side ponytail, use Bumble and Bumble Hairdresser’s Invisible Oil before styling. Finish with L’Oréal Elnett Satin Hairspray for a soft hold that maintains the sleekness without stiffness.
Sleek Straight Hair with Knit Headband
A sleek straight hairstyle paired with a cozy knit headband is a polished yet warm winter look. This style works best for long hair or medium hair and allows you to show off the smooth, glossy texture of your hair while keeping it controlled under the headband. The minimalist design of the knit headband adds warmth without overwhelming the hairstyle, making it a perfect option for both casual and formal winter outings.
Hair care tip: Use GHD Straight & Smooth Spray before straightening your hair to protect it from heat damage and keep it sleek throughout the day. Add shine and tame frizz with Moroccanoil Treatment for a smooth, glossy finish.
Textured Lob with Beret
A textured lob (long bob) paired with a stylish beret offers a chic, Parisian-inspired winter look. The lob’s soft waves and textured layers provide volume and movement, making this style ideal for medium-length hair. The beret adds a touch of sophistication, making this the perfect hairstyle for a day out in the city or a cozy coffee date.
Hair care tip: For added texture and definition, use IGK Beach Club Texture Spray to create natural waves. If you have finer hair, consider adding R+Co Dallas Thickening Spray to give your lob more volume.
Soft Waves with Fedora
For a laid-back yet sophisticated winter look, soft waves combined with a structured fedora offer the perfect balance. This style works well for long hair or medium hair, with the soft waves adding texture and the fedora bringing a modern, elegant touch. It’s a versatile style that can take you from casual daywear to an evening out in style.
Hair care tip: Create soft waves by using a large barrel curling iron and finishing with Oribe Wave and Shine Spray to add shine and hold. If your hair tends to frizz in winter, apply John Frieda Frizz Ease Extra Strength Serum for smoothness.
Slicked-Back Low Bun with Winter Beanie
For a sleek and minimalist winter hairstyle, the slicked-back low bun paired with a simple winter beanie is both practical and stylish. This hairstyle keeps your hair neat and tucked away, making it perfect for colder days when you want to keep your look fuss-free. This style works well for medium hair or long hair, and it offers a streamlined, sophisticated silhouette under your winter beanie.
Hair care tip: Use Redken Shine Flash 02 to give your bun a polished, glossy finish. If you have textured or frizzy hair, smooth it down with TIGI Bed Head After Party Smoothing Cream to keep everything in place.
Loose Side Braid with Pom-Pom Hat
A loose side braid combined with a playful pom-pom hat creates a relaxed, cute winter look. This style works for long hair or medium-length hair, with the braid adding texture and the pom-pom hat providing a whimsical, youthful vibe. It’s an easy, laid-back hairstyle that’s perfect for winter activities like ice skating or casual outdoor gatherings.
Hair care tip: To give your braid texture and volume, spritz Amika Un.Done Volume and Matte Texture Spray before styling. If you have curly hair, use Cantu Curl Activator Cream to define curls while keeping the braid soft and loose.
Tousled Curls with Earmuffs
Tousled curls paired with earmuffs create an effortlessly chic winter style that’s both cozy and cute. This look works especially well for those with curly hair or those who want to create loose, defined curls. The earmuffs keep you warm while letting your curls take center stage, making this style perfect for casual winter outings.
Hair care tip: Keep your curls defined and frizz-free by using Bumble and Bumble Curl Reactivator to refresh and hydrate your curls. If your curls need extra hold, finish with DevaCurl SuperCream Coconut Curl Styler for definition and shine.
Simple Low Chignon with Beanie
The simple low chignon is an elegant yet easy hairstyle to wear under a beanie. This look works for medium hair and long hair, offering a refined way to keep your hair neat without sacrificing style. The low chignon is a timeless choice, and when paired with a casual beanie, it creates a balanced look of sophistication and warmth.
Hair care tip: To create a smooth, sleek chignon, apply Aveda Smooth Infusion Nourishing Styling Crème to your hair before styling. Finish with Paul Mitchell Extra-Body Finishing Spray for a light hold that keeps everything in place.
Winter hats don’t have to ruin your hairstyle; instead, they can enhance your overall look when paired with the right hairstyle. Whether you’re sporting curly hair, long hair, or something shorter, these 25 hairstyles offer plenty of cute ideas to style your hair under winter hats. Feel free to experiment with different styles, and don’t forget to leave a comment below sharing your favorite winter hat hairstyle for 2024-2025!
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