20 Chic Beanie Hairstyles: Fashionable Pairings for Cold-Weather Days
Bad hair day or just feeling cozy? Either way, a beanie can turn your look from basic to effortlessly cool.
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Whether you’re heading to class, hitting the streets, or just skipping a wash day, the right hairstyle under your beanie makes all the difference. From soft waves to sleek braids, there’s no shortage of chic ways to wear your hat in style.
In this guide, we’ve rounded up 15 beanie-friendly hairstyles that keep things cute, comfy, and on-trend—no matter the weather. Let’s take your hat game to the next level.
#1. Tousled Waves with Classic Black Beanie
This effortless look brings laid-back charm with a touch of moody edge. Soft, tousled waves fall naturally over the shoulders, creating a lived-in texture that complements the muted palette.
A chunky rib-knit black beanie sits snugly, adding warmth and contrast against the cool blonde strands. Loose face-framing pieces soften the expression and highlight the brows and lips subtly.
Worn with a dark button-up shirt, the overall style leans into minimalism while still feeling expressive. It’s an easy go-to for cooler months when you want to feel cozy without sacrificing style.
#2. Sleek Pixie with Textured Knit Beanie
A clean pixie cut meets crisp makeup and a soft gray knit beanie for a modern, fashion-forward look. Wispy bangs peek out just enough to add a hint of edge, while the hair stays neatly tucked under the hat.
Her smooth skin and winged liner draw the eyes upward, balancing the cropped hairstyle with striking features. The dark gray ribbed beanie adds texture and warmth, contrasting well against her earth-toned sweater.
This look feels both bold and effortless—great for those who love sharp cuts and minimal fuss styling.
#3. Soft Curls with Frosted Gray Beanie
This look blends softness with winter charm. Loose curls cascade down naturally, creating a graceful shape that pairs beautifully with the ribbed gray beanie.
A center part gives the style a relaxed flow, while golden highlights bring out dimension in every strand. The matching knit sweater and subtle pendant necklace add a cozy, cohesive finish.
Light makeup and clear blue eyes complete the look, offering a fresh, approachable vibe that suits chilly mornings or weekend strolls. It’s a timeless style with quiet confidence and cold-weather ease.
#4. Voluminous Curls with Cozy Taupe Beanie
Bouncy curls bring rich volume and texture to this charming cold-weather look. The taupe beanie adds a relaxed shape up top, contrasting playfully with the structured definition of the glossy dark ringlets.
Soft pieces frame the face, letting natural movement take the lead. Her brows and lips carry warmth through subtle earthy tones, complementing the matching sweater in a way that feels effortlessly styled.
This look thrives on contrast—cozy yet bold, playful yet sophisticated. It’s a standout choice for curly-haired beauties who want to show off their texture while staying warm.
#5. Platinum Layers with Chunky Knit Beanie
Soft platinum strands fall just past the shoulders, giving this style a cool, airy feel. Choppy bangs peek out from beneath a thick beige beanie, framing the eyes with a casual softness.
Each layer adds movement, letting the hair feel light and touchable even under the weight of the hat. The muted tones of her sweater and hat keep the palette earthy and calm, drawing more attention to her bright eyes and textured hair.
It’s a modern, laid-back look that feels cozy yet bold—perfect for those winter days when you still want to make a quiet statement.
#6. Blunt Bob with Monochrome Beanie Mood
This look proves that simplicity can still make a strong impression. A sharp, chin-length bob adds crisp structure, with slightly tousled ends that soften the line just enough.
The black ribbed beanie hugs the head, pulling focus to bold brows and an expressive gaze. The grayscale tone enhances the contrast between fabric, hair, and skin, creating a timeless aesthetic that’s sleek and editorial.
Paired with a plain black crewneck and a sprig of lavender, the composition feels thoughtfully minimal. This is for anyone who appreciates strong lines, clean styling, and the quiet confidence of a classic cut.
#7. Feathered Bob with Earthy Beanie Accent
This playful yet earthy look pairs a feathered bob with a rich cinnamon-toned knit beanie. Wispy layers flick outward at the ends, bringing energy and lightness to the jawline.
A sprig of dried lavender tucked into the fold of the hat adds a charming, personal touch that feels both whimsical and grounded. Freckles peek through naturally, offering a soft texture against the clean lines of her sleeveless ribbed top.
Looking upward, the pose and styling together tell a story of quiet curiosity. This hairstyle works beautifully for those drawn to natural tones and airy silhouettes.
#8. Edgy Twin Braids with Street Beanie Vibe
Two loose braids anchor this edgy, street-style look with a nod to laid-back cool. Platinum-blonde strands frame the face with soft tendrils, adding movement beneath a snug black knit beanie.
A septum ring and layered silver jewelry give the outfit a subtle punk edge, while the black crewneck keeps it grounded. The contrast between soft textures and bold accessories makes this hairstyle feel both casual and expressive.
It’s a strong pick for anyone who blends alternative fashion with everyday wear—clean, bold, and unapologetically personal.
#9. Natural Ringlets with Soft Knit Beanie
Defined, springy curls frame the face in a way that feels warm and inviting. A creamy knit beanie adds softness up top, balancing out the volume and creating a cozy, winter-ready vibe.
Hair is left loose, letting each curl fall freely with movement and shape. The neutral sweater matches the hat’s tone, allowing the rich, dark hair to stand out effortlessly.
This look speaks to those who embrace their natural texture and want a style that feels both low-key and expressive. It’s all about softness, comfort, and letting your curls shine through.
#10. Soft Braided Pigtails with Chunky Knit Beanie
Two neat braids drape over each shoulder, giving this look a nostalgic charm that feels warm and grounded. The thick beige beanie adds texture while blending seamlessly with the matching ribbed turtleneck.
Her hair, parted down the center, stays smooth and polished with subtle waves that frame the face. Lavender held delicately in the frame adds a nature-inspired detail that complements the calm, cozy aesthetic.
This hairstyle is sweet without trying too hard—a soft expression of comfort, tradition, and modern simplicity.
#11. Side Braid Elegance with Soft Knit Layers
A single, chunky side braid adds graceful structure to this soft, neutral-toned look. Light blonde strands are gathered loosely, allowing delicate face-framing pieces to fall around the cheekbones.
The oatmeal beanie blends seamlessly with the oversized textured sweater, creating a palette that feels both calm and cozy. A small lavender sprig resting near the braid adds a gentle, floral detail without overpowering the style.
Everything about this look is relaxed yet intentional—subtle romance with a hint of countryside charm, perfect for crisp days spent indoors or out.
#12. Low Ponytail with Slouchy Black Beanie
A relaxed low ponytail paired with a slouchy black beanie offers an understated, modern silhouette. Long, straight strands flow down the back while loose tendrils frame the face for softness.
The oversized ribbed knit adds structure and weight up top, balancing the simplicity of the sleek hairstyle. The all-black outfit creates a clean, monochrome statement, while the soft lighting brings out natural tones in the hair.
This look is effortlessly cool—great for casual days when you want to keep it minimal but still polished.
#13. Blonde Box Braids with Mustard Knit Beanie
This standout look features sleek, two-toned box braids cascading from beneath a vibrant mustard beanie. The braids mix honey blonde with deeper roots, adding dimension and contrast that pop against her warm-toned sweater.
Each braid is neat and uniform, giving structure while still allowing freedom of movement. Glossy lips and soft neutral makeup enhance her natural glow, tying together the look with a fresh, radiant vibe.
Bold yet approachable, this hairstyle makes a statement without needing to shout—just the right blend of color, texture, and confidence.
#14. Back-Braided Simplicity with Cozy Knit Beanie
From the back view, this look captures quiet elegance through a single, loosely woven braid paired with a chunky oatmeal beanie. A few soft tendrils escape near the nape, adding a natural, undone charm.
The exposed shoulders and ribbed sweater bring in just the right amount of texture and softness, keeping the overall mood relaxed and intimate.
This hairstyle leans into minimalism with warmth—a timeless braid that’s easy to wear but always polished. It’s a calm and cozy style that feels right at home on any cool day.
#15. Chunky Pom-Pom Beanie with Loose Fall Braid
A relaxed boho braid winds its way down beneath a thick cable-knit beanie topped with a soft pom-pom. The loose, textured plait feels carefree and seasonal, echoing the golden autumn leaves scattered across the background.
Light blonde strands peek through in waves, creating contrast against the cozy cream sweater. The knit layers and earthy tones make this look feel like a crisp October afternoon—effortless, warm, and right in step with nature.
Whether you’re apple picking or enjoying a quiet outdoor moment, this hairstyle wraps you in comfort and casual charm.
#16. Defined Curls with Classic Black Beanie
Defined coils frame the face beautifully in this sleek and confident look. The rich texture of short natural curls contrasts with the snug fit of a thick black knit beanie, creating a clean silhouette with dimension.
A soft off-shoulder sweater and delicate chain necklace bring balance to the ensemble, adding grace to the bold, structured hairstyle. Minimal makeup lets the skin glow naturally, emphasizing the radiant finish.
This style is equal parts polished and playful—perfect for showcasing natural curl patterns while staying warm and stylish through the season.
#17. Messy Bun with Cable-Knit Beanie Charm
This look pairs practicality with laid-back beauty. A cozy gray cable-knit beanie sits snugly over a messy bun that peeks out from the top, offering a casual updo perfect for brisk autumn days.
A single maple leaf resting on her shoulder adds a poetic touch, connecting the scene with the earthy, muted tones of the season. Loose strands frame the face softly, and the knit sweater ties everything together for a monochrome moment.
This hairstyle feels spontaneous and relaxed—like a morning coffee walk under falling leaves.
#18.Snowy Sleek Ponytail with Cable-Knit Beanie
This winter-ready style combines sleekness with warmth. A light gray cable-knit beanie hugs the head snugly while allowing a smooth, high ponytail to flow freely from the back.
The ponytail keeps the look neat and practical, perfect for snowy strolls or outdoor activities. Frosted details rest lightly on the hat and shoulders, adding seasonal texture to the scene.
The clean lines of her dark outerwear create a crisp contrast against the soft beanie and falling snow. It’s a fresh, sporty look that balances utility with style—simple, strong, and beautifully winterproof.
#19. Double Braids with Playful Pom-Pom Beanie
This fun and youthful look features twin braids that fall neatly over a casual layered outfit, anchored by a whimsical gray beanie with two plush pom-poms on top.
The hairstyle is simple yet structured, allowing the accessories to shine while keeping the hair tidy and expressive. A denim jacket layered over a hoodie adds a street-style edge, while the warm evening light in the background brings a golden softness to the overall vibe.
It’s a look that feels approachable, a little playful, and just right for chilly walks or sunset meetups.
#20. Braided Crown Bun with Loose Face-Framing Plaits
This style blends elegance and ease with a crown bun wrapped in neat braids and face-framing plaits left to softly drape on each side. The warm brown beanie sits slightly slouched, adding relaxed contrast to the structure of the braids.
Subtle caramel tones woven through the braids bring dimension and highlight the natural warmth of her skin. A delicate hummingbird tattoo on her shoulder adds a personal, artistic touch that complements the simplicity of the outfit.
It’s a graceful and grounded look—perfect for those who carry confidence in every detail.
Aria Winslow
Zara Montoya, a trailblazing hairstylist and innovative beauty expert, is the dynamic Editor-in-Chief of StyleStrands Magazine.
Drawing from her two decades of transformative experience in high-end salons and fashion runways, Zara curates cutting-edge hair trends and timeless techniques.
Her groundbreaking approach to hairstyling has inspired countless individuals to reimagine their personal aesthetic and embrace bold self-expression.
Zara’s guiding principle: Every strand tells a story, and your hair is the most personal canvas of creativity.
