Stunning Winter Medium Haircuts to Keep You Stylish All Season 25 Ideas

Winter is the perfect time to refresh your look, and what better way to do that than with a chic medium haircut? Whether you’re looking for a shoulder-length style with soft layers, bold bangs, or effortless waves, medium haircuts offer endless versatility. In this guide, we’ll explore 25 of the most stylish winter medium haircuts, perfect for all hair types and face shapes. From classic cuts to trendy new styles, you’ll find the ideal look to keep you feeling fresh and fabulous all season long. Ready to find your next favorite hairstyle? Let’s dive into the top ideas for this winter!

Winter-Ready Medium Waves

Winter is the perfect season to embrace voluminous waves that fall just below the shoulders. This medium-length haircut is soft, face-framing, and ideal for those who love a bit of texture without going too short. The waves add a level of elegance while maintaining that casual, “just rolled out of bed” vibe—perfect for winter get-togethers or cozy nights by the fire.

This look is best suited for women with round faces as the loose waves help to elongate the face, balancing out soft features. It’s also a great option for those with thick hair, as the waves can create volume and reduce heaviness. Those with very fine hair may need additional styling products to achieve this effect, so it might not be the best choice for thin hair types looking for a low-maintenance cut.

To keep the waves looking fresh during the winter months, use a moisturizing styling cream that adds definition while protecting your hair from dry winter air. Moroccanoil Curl Defining Cream or Olaplex No. 6 Bond Smoother would be great for enhancing the texture and protecting the strands. To avoid frizz, don’t forget a serum that locks in moisture.

The face-framing layers of this haircut can be particularly flattering. You can play up the texture for added drama, or keep the waves soft and gentle for an everyday, natural look. Either way, this is one of the best winter medium haircuts for creating effortless charm.

Shoulder-Length Curtain Bangs

Curtain bangs are having a major moment, and this medium-length cut paired with soft, sweeping bangs proves why. Falling at shoulder length, this haircut offers an ideal balance for those looking to try bangs without committing to a full fringe. The bangs frame the face beautifully, giving off a chic, low-maintenance vibe that pairs perfectly with cozy winter sweaters.

This style works exceptionally well for those with oval faces and wavy hair, as the bangs break up the length of the face, creating softness around the features. It’s also ideal for thick hair, as the layers reduce bulk and provide movement, giving the cut dimension and texture. For thin hair, you might want to consult your stylist about adding extra layers to avoid making your hair appear flat.

To maintain the shape of these bangs in winter, use a lightweight hairspray that won’t weigh them down. Amika Fluxus Touchable Hairspray is perfect for this, as it keeps your style intact without compromising the natural movement of the bangs. Pair it with a volumizing mousse like Bumble and Bumble Thickening Full Form Mousse for extra lift at the roots.

Curtain bangs also offer a nostalgic nod to 70s trends, which makes them perfect for adding a bit of retro aesthetic to your winter wardrobe. This is a fun and youthful take on medium hairstyles that never go out of style.

Soft Layers with Ashy Tones

For a modern winter look, consider this shoulder-length cut with ash-toned highlights. The medium-length layers add movement and depth, while the ashy color reflects the cold hues of the season. This is an excellent look for those who want something fresh and cool to match the crisp winter air.

This style is best suited for straight hair and works well for both thick and thin hair types. The layers help create the illusion of volume for those with finer strands, while the soft texture ensures that thicker hair doesn’t become too bulky. It’s also a great option for women over 50, as the ash tones provide a sophisticated edge that’s timeless and elegant.

To maintain the cool ashy hue, you’ll need to invest in a purple shampoo like Fanola No Yellow Shampoo or Redken Color Extend Blondage to prevent brassiness. Regular deep conditioning with a hydrating mask like Briogeo Don’t Despair, Repair! Deep Conditioning Mask is essential to keep the hair looking shiny and healthy through the colder months.

The soft layers around the face add a gentle framing effect, making this cut ideal for anyone who prefers an understated yet modern look. It’s one of the best winter medium haircuts for adding some subtle sophistication to your style.

Rich Burgundy Waves

This shoulder-length cut with rich burgundy waves is the epitome of winter warmth. The deep color brings out the best of the season, while the soft waves add dimension and volume. The medium length makes this style versatile and easy to maintain, offering a bold yet approachable look.

This cut works well for round faces and oval faces alike, as the waves help to elongate the face. It’s also an excellent choice for those with thick hair, as the waves add movement without overwhelming the natural volume. Thin hair types can also achieve this look with the help of a curling wand and volumizing products like Living Proof Full Dry Volume Blast.

Maintaining rich colors like burgundy in winter can be a challenge due to the drying effects of the season. Using a color-safe shampoo and conditioner like Pureology Hydrate Shampoo and Conditioner is crucial to maintaining vibrancy. A gloss treatment every few weeks can also help keep the color looking fresh.

This hairstyle is perfect for anyone looking to make a statement. The deep burgundy color stands out in any winter setting, and the waves give it that effortlessly chic vibe. It’s the kind of look that turns heads and radiates confidence.

Feathered Winter Shag

The medium-length shag with feathered layers is a carefree, low-maintenance option that embraces texture and volume. With its effortless side part and layered ends, this cut gives off a rebellious yet polished vibe—ideal for the cooler months.

This style is perfect for those with wavy hair or curly hair, as the layers enhance the natural texture without requiring too much styling. It’s also a great choice for those with round faces, as the layers help to define and elongate the face shape. For thick hair, this cut reduces bulk, while for thin hair, it creates the illusion of fullness.

To style this cut, all you need is a texture spray like Ouai Wave Spray or Oribe Dry Texturizing Spray to emphasize the layers and keep them from falling flat. This is one of those shoulder-length hairstyles that works well with minimal effort, which is always a plus during the busy winter months.

The feathered layers offer a playful, textured look that feels modern yet timeless. It’s a stylish yet functional haircut for women who want something edgy without the need for constant upkeep.

Textured Medium Bob

This textured medium bob is the perfect winter hairstyle for anyone looking to embrace a low-maintenance yet stylish cut. The blunt ends and natural waves add dimension while keeping the length manageable, making it an ideal shoulder-length option for women who want something chic yet easy to maintain. The soft waves give this cut a bit of texture, making it look effortlessly undone.

This look works wonderfully for women with round faces and oval faces, as the slight wave and length help balance out facial features. It’s also a great choice for thick hair, as the weight at the ends keeps everything controlled. Those with thin hair might need a bit of styling mousse or texturizing spray to add volume to the body of the hair.

To maintain the waves, use a light texture spray like Ouai Wave Spray to emphasize the layers and give your hair that perfectly tousled look. Adding a heat protectant such as Gisou Propolis Infused Heat Protecting Spray before styling will also ensure that your hair stays healthy through the winter months.

The versatility of this cut means you can keep it polished or play up the texture for a more laid-back, relaxed winter look. It’s one of those Winter Medium Haircuts that seamlessly fits into both professional and casual settings.

Warm Copper Waves

For those looking to add a bit of warmth to their winter look, these long copper waves are perfect. The rich, warm tones add a beautiful glow to the hair, while the soft, cascading waves provide plenty of movement and volume. The contrast between the darker roots and lighter ends creates depth, making this hairstyle stand out even more.

This look is best suited for women with round faces or oval faces, as the length of the waves helps elongate the face, while the color adds a flattering warmth. Thick hair is ideal for achieving these voluminous waves, but thin hair types can also pull off this look with the help of a volumizing spray like Living Proof Full Dry Volume Blast to add body.

To keep the copper tones vibrant throughout the winter months, it’s important to use a color-safe shampoo and conditioner like Pureology Hydrate Shampoo and Conditioner. Regular deep conditioning treatments will help keep the hair hydrated and prevent fading.

These warm copper waves are perfect for the colder months, adding a touch of brightness and energy to your winter look.

Sleek Asymmetrical Bob

This sleek asymmetrical bob brings an elegant edge to the classic short hairstyles of winter. The slightly longer front combined with a smooth, glossy finish gives this bob a modern twist that is both sharp and stylish. The warm brunette hue with subtle highlights adds extra dimension, making the color pop even in colder weather.

This look is fantastic for women with oval faces or round faces because the asymmetry helps create the illusion of length. It’s also ideal for straight hair types, as the sleekness and structure are best maintained on naturally straight locks. Thick hair works well here, as the blunt ends add weight and shape. Thin hair can also achieve this style but may require some added volume at the roots.

For keeping this sleek bob looking smooth throughout the winter, use a smoothing serum like Bumble and Bumble Hairdresser’s Invisible Oil to lock in shine and protect against dryness. A flat iron can also help maintain the straight structure, ensuring the asymmetry remains sharp.

This haircut exudes sophistication and is perfect for anyone looking to make a subtle yet impactful statement this winter.

Soft Blonde Waves

These soft blonde waves offer a gorgeous blend of texture and light, making this style one of the most flattering Winter Medium Haircuts for brightening up the season. The blonde color, with its light, icy undertones, reflects the wintery hues, while the soft waves add a relaxed, beachy feel.

This style works well for oval faces and round faces alike. The waves add movement and soften facial features, making it a flattering option for those with thick or thin hair. The length also falls perfectly at the shoulders, which is ideal for keeping things manageable without losing volume or texture.

Maintaining the blonde shade requires consistent care, especially in winter. A purple shampoo like Fanola No Yellow Shampoo can help keep brassiness at bay, while a deep conditioning treatment like Olaplex No. 3 Hair Perfector will keep your waves hydrated and looking healthy.

This hairstyle is versatile enough to be worn for any occasion, from casual winter weekends to holiday parties, thanks to its natural yet polished appearance.

Layered Fringe with Waves

This medium-length cut with soft waves and a layered fringe is ideal for winter styling. The fringe brings a touch of softness to the overall look, while the loose waves add a bit of texture and movement. This combination offers a perfect balance of structure and flow, making it a go-to for women wanting a laid-back yet fashionable winter look.

The fringe makes this cut especially flattering for round faces and oval faces, as it helps break up the face and add a bit of length. It’s a versatile look that works for both thick and thin hair, thanks to the face-framing layers that give the style its lightweight, airy feel.

To maintain this look during the winter, opt for a lightweight hairspray like Amika Fluxus Touchable Hairspray to keep the waves in place without weighing down the fringe. Regular trims will also help maintain the fringe’s sharpness while preventing it from growing too long.

This medium-length, layered cut with a fringe is the perfect option for a casual winter style that doesn’t require much effort but still makes an impact.

Subtle Highlights and Layers

This medium-length cut with subtle highlights is perfect for those who want a fresh yet understated winter look. The highlights create a natural sun-kissed effect, adding dimension and movement to the hair. Paired with soft layers, this style adds volume without being overpowering, making it ideal for an everyday look that’s both elegant and easy to maintain.

This haircut works especially well for oval faces and round faces, as the layers frame the face beautifully without adding too much bulk. It’s a great choice for women with thick hair, as the layers help to reduce weight while adding movement. For those with thin hair, the subtle highlights can give the illusion of fuller locks.

To maintain this look, use a shine-enhancing product like Oribe Gold Lust Nourishing Hair Oil to keep the highlights vibrant. A lightweight conditioner, such as Davines OI Conditioner, will ensure that the layers don’t weigh down the hair, preserving the volume and bounce.

This layered cut is a wonderful choice for women who want a polished, low-maintenance hairstyle that still feels elevated for winter.

Classic Blunt Bob

The classic blunt bob is a timeless look, and this sleek, jet-black version takes it up a notch. The sharp cut and smooth finish give this bob a bold, modern edge that’s perfect for those who love a minimalist aesthetic. The length falls just above the chin, creating a flattering silhouette that frames the face and emphasizes sharp features.

This cut is ideal for oval faces and round faces, as the bluntness helps to elongate the jawline and create balance. It works best for straight hair, as the sleekness of the cut is most easily maintained with naturally straight textures. Thick hair types will appreciate the structure this bob provides, but thin hair can achieve a similar look with volumizing products.

To keep this blunt bob looking sleek and shiny, a smoothing serum like Kerastase Elixir Ultime L’Huile Original Hair Oil is essential. A flat iron can help maintain the sharpness of the cut, ensuring that the ends remain crisp.

This style is perfect for winter, adding a sharp, modern edge to your wardrobe while remaining effortlessly chic.

Voluminous Layered Bob

This voluminous layered bob combines sleekness and volume to create a bold, structured look. The layers add plenty of body, while the rounded shape at the back gives the cut a polished finish. The subtle highlights running through the length add depth and dimension, making this bob stand out.

Best suited for round faces and oval faces, the layers help elongate and frame the face, while the rounded shape adds softness. It’s a fantastic option for women with thick hair, as the layers help manage the volume, creating a sculpted look. Thin hair types can achieve this look with some texturizing spray for added volume and body.

To style this voluminous bob, use a lightweight mousse like Bumble and Bumble Thickening Full Form Mousse to add lift at the roots. A round brush will help shape the layers and keep the style looking polished.

This bob is perfect for women looking for a stylish, volumized look that adds sophistication to any winter ensemble.

Sleek Copper Layers

This sleek, shoulder-length cut with warm copper tones brings vibrancy to winter. The straight texture paired with subtle layers adds elegance, while the rich copper color ensures the hair stands out. This cut is ideal for women who want a sophisticated yet warm look for the colder months.

This hairstyle is perfect for oval faces and round faces, as the sleek lines and layers create a slimming effect. It’s ideal for straight hair types, as the sleekness is easier to maintain without much effort. Thick hair works particularly well with this cut because the layers help reduce weight, while thin hair can benefit from added texture through styling products.

To maintain the vibrancy of the copper color, use a color-safe shampoo like Redken Color Extend Magnetics Shampoo. A smoothing serum like Moroccanoil Treatment will keep the sleekness intact and prevent winter frizz.

This sleek, copper-toned cut is perfect for those who want a vibrant yet polished winter look.

Golden Wavy Lob

This golden wavy lob (long bob) is a stunning option for winter, adding warmth and softness to your overall look. The waves add texture, while the golden blonde color brightens up the hair, making it a fantastic choice for those looking to liven up their style during the colder months. The length falls perfectly at the shoulders, making it versatile and easy to style.

This hairstyle works beautifully for round faces and oval faces alike, as the waves help frame the face and soften its features. It’s great for thick and thin hair, as the waves add volume and dimension to any texture.

To maintain the softness of the waves, use a lightweight mousse like Amika Plus Size Volume & Body Mousse to keep the waves bouncy. For those wanting to keep their golden tones looking fresh, a color-enhancing shampoo like Oribe Bright Blonde Shampoo will keep brassiness at bay.

This wavy lob is ideal for women who want a warm, easy-to-maintain style that adds a touch of brightness to their winter look.

Soft Wavy Lob

This medium-length lob with soft waves is a modern take on the classic bob, bringing effortless elegance to winter hairstyles. The gentle waves give the cut texture and movement, making it an ideal choice for women who want a style that’s polished but not too structured. The dark brown hue adds richness and depth, giving this cut a naturally sophisticated feel.

This look is perfect for round faces and oval faces alike, as the waves help to elongate the face while keeping the overall silhouette soft. It works well for thick hair, as the layers reduce bulk while adding movement, but thin hair types can also benefit from using a volumizing spray to enhance the waves.

To maintain the soft waves, use a light mousse like Bumble and Bumble Surf Foam Spray for added texture without weighing down the hair. A hydrating mask like Moroccanoil Intense Hydrating Mask will keep your hair moisturized and shiny throughout the colder months.

This lob is perfect for anyone seeking a low-maintenance yet stylish winter look that can easily transition from day to night.

Platinum Blonde with Middle Part

This sleek, platinum blonde look is all about crisp lines and a stunning icy color. With its clean middle part and smooth, straight texture, this cut is perfect for winter, giving off an air of sophistication and minimalism. The length falls just at the shoulders, making it easy to maintain while still offering enough versatility for different styling options.

This cut works best for oval faces, as the middle part and sleek lines highlight symmetrical features. It’s also perfect for thin hair, as the platinum shade can add dimension and depth to finer textures. However, thick hair types can also pull off this look with the right products to keep it smooth and manageable.

To keep platinum blonde hair looking fresh, a purple shampoo like Fanola No Yellow Shampoo will prevent any brassiness. For maintaining the sleekness, a smoothing serum like Redken Frizz Dismiss will keep your strands shiny and frizz-free, even in the winter.

This winter-ready platinum blonde cut is perfect for those who love clean lines and a bold, striking color.

Sharp Bob with Blunt Bangs

This sharp bob with blunt bangs is the epitome of high-fashion winter hairstyles. The straight, blunt lines of the bob paired with the edgy bangs create a bold look that demands attention. The jet-black color gives the cut a sleek, modern finish, making it a great choice for women who love minimalist yet daring styles.

This cut is ideal for oval faces, as the bluntness of the bangs and bob creates a balanced, symmetrical appearance. It works especially well for straight hair, as the sleekness of the cut is easier to maintain. Thick hair can benefit from the structure of this bob, but thin hair may need some volumizing products to ensure the look doesn’t fall flat.

To keep this bob looking sharp, use a flat iron and a heat protectant like GHD Heat Protect Spray to maintain the sleekness. A shine serum like Biosilk Silk Therapy will add extra gloss, ensuring the cut stays polished throughout the winter.

This blunt bob is perfect for those who want a bold, fashion-forward look this winter.

Silver Ash Waves

This silver ash wavy bob brings cool tones and texture to the forefront, making it a standout winter look. The waves give this bob plenty of movement, while the ash-silver color is perfect for those wanting to embrace winter’s icy hues. The length is short enough to be manageable but long enough to offer styling versatility.

This cut is great for oval faces and round faces, as the waves soften the features and add a touch of playfulness. Thick hair works well with this cut, as the waves help reduce weight and add texture. Thin hair types can create extra volume with the help of a curling wand and texturizing spray.

To keep the silver color vibrant and free from yellow tones, a purple shampoo like Matrix Total Results So Silver Shampoo is essential. For the waves, a styling product like Ouai Wave Spray will add definition without making the hair feel stiff.

This silver ash wavy bob is perfect for anyone looking to make a statement this winter with both color and texture.

Rich Chocolate Waves

This medium-length style with rich chocolate waves is all about luxury and softness. The deep chocolate hue adds richness and warmth to the hair, while the loose waves create a soft, romantic feel. This cut is perfect for winter, as it brings a sense of warmth and richness to the overall look.

This style works beautifully for round faces and oval faces, as the waves help to soften facial features and add dimension. It’s ideal for thick hair, as the waves enhance the natural volume without making the hair feel too heavy. Thin hair types can also achieve this look with the help of a curling wand and volumizing spray.

To keep the waves defined, use a curl-enhancing cream like DevaCurl Wave Maker to add texture and movement. A gloss treatment like John Frieda Brilliant Brunette Luminous Glaze will help maintain the shine and vibrancy of the chocolate color.

This rich chocolate wavy style is perfect for women who want a soft, elegant look that can be dressed up or down throughout the winter months.

Dimensional Blonde Waves

This dimensional blonde wavy cut is all about adding depth and texture to your medium-length hair. The darker roots blending into bright blonde ends create a gorgeous ombré effect, perfect for winter when lighter tones can brighten up your entire look. The soft waves add movement and bounce, making this hairstyle feel both relaxed and polished.

This look works beautifully for oval faces and round faces, as the layers of waves frame the face without adding bulk. It’s ideal for thick hair, as the waves help distribute the volume, but thin hair can also achieve this look with a volumizing mousse to give the waves more body.

To maintain the brightness of the blonde, use a color-safe shampoo like Redken Blondage High Bright to keep the tones from fading. A beach wave spray like Ouai Wave Spray will also enhance the texture and hold the waves in place without weighing them down.

This style is great for those who want a laid-back, wavy look that’s still full of dimension and depth throughout the winter.

Vibrant Fiery Red

For those looking to make a bold statement this winter, this vibrant fiery red hair is the way to go. The color alone is stunning and eye-catching, making this sleek, straight style stand out in any crowd. With its smooth texture and intense red hue, this look demands attention while giving off a fierce, confident vibe.

This color works well for oval faces and round faces, as it adds drama and depth to the hair. It’s also perfect for women with straight hair since the sleekness allows the color to shine even more. Thick hair will hold the bold color beautifully, but thin hair may need a shine serum like Kenra Platinum Silkening Gloss to maintain that glossy finish.

To keep the fiery red color vibrant throughout the winter, use a color-depositing shampoo like Joico Color Infuse Red Shampoo. Regular moisturizing treatments will also help maintain the sleekness and avoid dryness from winter air.

This bright red style is the ultimate choice for anyone wanting to add a burst of color and personality to their winter hairstyle.

Curly Shag with Fringe

This curly shag with a fringe embraces natural texture and volume, making it a standout choice for curly-haired women this winter. The soft pink hue adds a touch of fantasy, while the curly fringe gives the cut a playful and trendy vibe. The layers are cut to enhance the curl pattern, creating a bouncy and full shape that moves effortlessly.

This style is ideal for round faces and oval faces, as the fringe helps to frame the face and add balance. It’s a fantastic option for women with thick, curly hair who want to embrace their texture without too much styling effort. Thin hair can achieve this look with a curl-enhancing mousse to give the curls more definition and volume.

To keep the curls defined and frizz-free, use a curl cream like DevaCurl SuperCream to hydrate and shape the curls. A color-safe shampoo will also help keep the pastel pink tone vibrant and long-lasting.

This curly shag is perfect for anyone looking to embrace their natural curls while adding a touch of fun and color to their winter style.

Rich Copper Waves

This rich copper wavy cut is a warm, vibrant choice for winter, adding depth and brightness to your overall look. The copper hue is rich and dimensional, perfect for women who want to embrace bold colors during the colder months. The soft waves add a romantic, effortless feel, making this style both polished and playful.

This look is flattering for round faces and oval faces, as the waves create a slimming effect around the jawline. It works best for thick hair, as the waves help manage the volume, but thin hair can also achieve this look with a texturizing spray to add more body.

To maintain the richness of the copper color, use a color-safe shampoo like Matrix Total Results Keep Me Vivid Shampoo. A lightweight mousse like Amika Plus Size Volume & Body Mousse will help keep the waves bouncy and full.

This copper wavy style is perfect for adding a touch of warmth and vibrancy to your winter wardrobe.

Vintage-Inspired Waves

These vintage-inspired waves take a modern twist on classic Hollywood glam. The sleek, structured waves add a touch of elegance to any winter look, while the dark brown hue with subtle lighter ends creates dimension and depth. This style is perfect for special occasions or anytime you want to elevate your hairstyle.

This look works well for oval faces and round faces, as the waves create an elongated, elegant silhouette. Thick hair is ideal for holding the structured waves, but thin hair can achieve the same look with a curling iron and a strong-hold hairspray like Oribe Superfine Hair Spray.

To keep these waves looking sleek and shiny, use a shine serum like Moroccanoil Treatment to smooth down any frizz. A heat protectant spray is also crucial for maintaining the health of the hair while using hot tools to create this vintage-inspired look.

These elegant waves are a perfect winter option for anyone looking to channel old Hollywood glamour with a modern twist.