Winter is the perfect time to experiment with different hairstyles that complement your favorite hats. Whether you prefer short hair, long hair, or medium-length styles, there’s a hat-hairstyle combination for everyone. Below, we’ve curated a list of 27 winter hat hairstyles for the upcoming 2024-2025 season, each designed to inspire your look while keeping you stylish and warm.
#27 Sleek Bob with a Headband
This sleek bob, paired with a simple headband, creates an elegant winter look that’s ideal for women with short hair. The headband adds warmth while keeping flyaways in place, perfect for cold, windy days. Style the bob straight for a clean, polished finish.
#26 Casual Hairstyle and Baseball Cap
For an effortless, sporty style, a casual hairstyle tucked beneath a baseball cap is a perfect match. This look works well with long hair or medium-length hair, giving you a laid-back vibe whether you’re heading to the gym or running errands. The cap keeps your hair under control while adding a casual, relaxed touch.
#25 Glamorous Loose Waves with a Silk Headscarf
If you’re a fan of glamorous looks, loose waves styled under a colorful silk headscarf bring both warmth and style. This look is great for curly hair or long hair. The headscarf serves as both a stylish accessory and a way to protect your hair from the winter chill.
#24 Chic Blunt Bob with a Fedora
A fedora paired with a blunt bob gives you that vintage, chic edge perfect for winter outings. The structured hat adds sophistication, making it an ideal look for both casual and dressier events. Best suited for short hair, this combo can easily elevate any outfit.
#23 Relaxed Waves with a Beret
A classic beret paired with relaxed waves is a timeless winter look. Women with medium-length hair can rock this effortlessly Parisian vibe, perfect for both casual and formal settings. The beret adds warmth without compromising on style.
#22 Short Curly Hair and a Faux Fur Hat
For women with short curly hair, a faux fur hat is both functional and fashionable. This winter-ready combination adds volume and texture to your look while keeping you cozy during chilly days. It’s a great choice for outdoor events or simply adding a bit of flair to your outfit.
#21 Winter Glam with a Faux Fur Hat
This elegant look is achieved with a chic faux fur hat, perfect for long hair or medium-length hair. The fur hat not only adds a luxurious element but also keeps you warm during the cold winter months. Paired with sunglasses and gloves, this look is both functional and stylish for any winter setting.
#20 Urban Edge with a Wide-Brimmed Hat
For a bold, city-ready look, this outfit features a wide-brimmed hat that’s ideal for women with long wavy hair. The hat adds an edgy element to the look, while the curls soften the overall vibe. Perfect for urban adventures, it complements both casual and chic ensembles with ease.
#19 Vibrant Style with a Faux Fur Beret
This look takes a daring approach with a bright faux fur beret, ideal for short hair or women with curly hair. The pop of color elevates any outfit, and the beret’s texture adds a luxurious feel to the style. A great choice for those looking to make a statement this winter season.
#18 Leopard Print Beret for a Playful Winter Look
A leopard print beret is the ultimate accessory for a playful, chic winter outfit. Paired with voluminous, wavy long hair, this look is ideal for women who want to stand out while staying warm. The beret adds a touch of personality, making it a versatile piece for any winter wardrobe.
#17 Minimalist Elegance with a White Hat
This minimalist approach features a sleek white hat paired with flowing, long hair. The simplicity of the hat contrasts beautifully with the intricate waves, creating an effortlessly elegant winter look. Ideal for women seeking a clean, polished aesthetic for the colder months.
#16 Cozy Chic with a Newsboy Cap
A newsboy cap paired with medium-length hair creates a cozy yet stylish winter ensemble. The cap adds a vintage touch to the look, while the waves give it a modern twist. Perfect for winter getaways, this outfit combines both comfort and chic elements seamlessly.
#15 Cozy Elegance with a Wrapped Hood
This winter-ready look features a warm hood wrap that effortlessly frames the face. Ideal for medium-length hair, the wrap adds both elegance and warmth, perfect for those cold outdoor walks. Pair it with a plush coat to enhance the cozy, chic winter vibe.
#14 Classic Faux Fur Hat for a Ski Resort Look
This fun winter look showcases a classic faux fur hat, paired with long wavy hair for an easygoing, après-ski style. The faux fur hat adds a touch of sophistication while keeping you warm, making it perfect for winter resorts and outdoor adventures alike.
#13 Sleek Braid and a Beanie for the Slopes
Ideal for ski trips, this look pairs a sleek, long braid with a casual beanie. The braid is practical and stylish, staying intact during all your winter activities, from snowboarding to skiing. The beanie adds a laid-back feel while keeping your head warm on the slopes.
#12 Luxe Winter Whites with a Wide-Brim Hat
This monochrome look features a structured wide-brim hat, paired with a full white outfit, making it perfect for long hair. The hat adds a layer of sophistication to the minimalistic look, ideal for cozy winter escapes by the lake. It’s the ultimate blend of comfort and chic.
#11 Chic Short Hair with a Black Fur Hat
For a bold winter style, this black fur hat perfectly complements short hair. The oversized hat adds a touch of drama, while the short bob haircut keeps the look edgy and modern. It’s a perfect choice for women who want to make a statement with their winter style.
#10 Casual Cool with a Baseball Cap
This laid-back winter look features a simple baseball cap, paired with a short bob haircut. The cap adds a sporty element to the outfit, making it a perfect option for casual, everyday winter wear. It’s an easy, go-to accessory for those on the go.
#9 Bold Leopard Vibes in Winter
The bold leopard print coat is a timeless classic but with an added winter flair. The model’s coat, combined with a black knit hat, transforms this look into a chic winter statement. The long, structured fit of the coat keeps it sleek while the snow accents the luxurious feel of the fabric. This fierce yet cozy combination is all about balancing wild prints with sophisticated styling.
#8 Luxe Comfort in a Chanel Winter
Nothing says winter chic like these Chanel earmuffs paired with a cozy bomber jacket. The soft shearling lining and iconic logo are elevated by deep plum lips, which bring an edgy yet polished touch. With her collar up, this look blends warmth and luxury effortlessly. Perfect for city strolls or cozying up in a car, this outfit balances glam with practicality.
#7 Sophisticated City Elegance
A classic button-down never looked so sophisticated. Paired with high-waisted jeans and a striking red-accented cap, this city street style exudes a polished, business-meets-casual vibe. The accessories — a structured handbag and layered jewelry — complete the look with a subtle yet powerful punch. Ideal for a day of city shopping or meetings, this outfit mixes professional with effortless style.
#6 Autumn Elegance by the Lake
With crisp fall leaves underfoot, the oversized gray coat and neutral tones of this ensemble speak of timeless autumnal elegance. A wide-brimmed hat adds drama while the monochrome palette keeps things sophisticated. The tranquil setting by the lake only adds to the ethereal beauty of this look, making it perfect for a dreamy fall afternoon stroll or an outdoor event in cooler weather.
#5 Urban Cool in Cozy Layers
Sporting a street-ready hoodie with an oversized, plush underlining, this outfit screams urban cool. The mix of textures, from the soft hoodie to the sleek black cycling shorts, makes this look effortlessly stylish. Throw on some trendy glasses and you’re ready to hit the city streets with a chic yet comfortable vibe that transitions from casual to standout with ease.
#4 Modern Cozy Chic
With her chunky knit beanie and a cozy shearling-lined coat, this look is all about embracing the chill in style. The long wool socks peeking out of her boots add a playful touch, while the sleek black dress underneath offers an element of contrast. This is the ultimate in modern winter chic — perfect for strolling through the Parisian streets or heading to a festive gathering.
#3 Athletic Streetwear Luxe
Athleisure has never looked more polished than in this city street style. A perfectly tailored gray coat and oversized gold chain bag add an element of high fashion to the casual vibe of leggings and sneakers. The baseball cap keeps it sporty, while the coat elevates the entire ensemble. This outfit is a masterclass in blending high-end luxury with laid-back streetwear.
#2 Tropical Green Dream
This playful and vibrant look brings the tropics into the city. With a bold green blazer and a fresh white baseball cap, the mix of professional structure and casual elements makes this a standout style. The addition of a striped scarf adds a dash of personality, while the woven handbag keeps the overall feel grounded and easygoing. Perfect for an afternoon of exploring urban jungles with flair.
#1 Cozy Cable Knit Charm
The oversized cable knit sweater paired with vibrant red earmuffs is the ultimate in cozy winter styling. The textures in this look offer a sense of warmth and softness, while the deep red accessories add a pop of color to the neutral palette. This casual yet charming outfit is perfect for embracing the cold while staying effortlessly stylish.
