37 Winter Medium Haircuts for 2024-2025: Trendy Looks to Keep You Stylish All Season

Winter 2024-2025 is all about fresh styles and updated trends, especially for medium-length hair. Are you looking to transform your look, while staying fashionable and season-appropriate? With a mix of layers, textures, and bangs, these cuts are perfect for various face shapes, especially round faces. Dive into the season’s most fashionable hairstyles with our comprehensive guide featuring the latest shoulder-length cuts that flatter all hair types. Let’s explore the color ideas for brunettes and styles that will inspire your winter hair journey.

Layered Lob with Soft Waves

The Layered Lob with Soft Waves is a timeless hairstyle that fits perfectly into winter trends for 2024-2025. This shoulder-length cut features subtle layers, which add depth and movement, creating an effortlessly chic look. The soft waves give the haircut texture and dimension, making it perfect for anyone with straight or slightly wavy hair. This style suits round faces as it elongates the face shape and adds structure. Whether you’re attending a casual outing or a festive event, this lob pairs beautifully with winter wardrobes.

To keep the waves in shape and frizz-free during the colder months, opt for hair products like the Ouai Wave Spray or the Moroccanoil Curl Defining Cream. These products will help define your waves while maintaining moisture, which is essential in dry winter air. Regular trims will keep your layers looking fresh, and a silk pillowcase will reduce friction, keeping your hair smooth.

Choppy Shoulder-Length Cut

The Choppy Shoulder-Length Cut is all about edgy texture and modern hairstyles. This cut features uneven, choppy layers that give your hair an effortless and playful appearance. Ideal for those looking to add volume and movement, this shoulder-length hairstyle works wonders for those with thin or fine hair, as the layers create the illusion of thickness. It’s also a great fit for round faces, as the choppy layers help balance and add angles to the face.

For maintaining this textured cut, use the Living Proof Full Dry Volume Blast for instant volume and lift. Additionally, a sea salt spray like Bumble and Bumble Surf Spray can enhance the choppiness by giving your hair that lived-in texture without weighing it down.

Blunt Cut with Curtain Bangs

For those who prefer sleek, structured hairstyles, the Blunt Cut with Curtain Bangs is the epitome of winter elegance. The blunt cut adds thickness and a sharp outline to your hair, while the curtain bangs frame your face beautifully, particularly flattering for round faces. This cut can be worn straight for a polished look or tousled for a softer, more casual style. It’s a versatile choice for winter 2024, giving off a clean yet stylish vibe.

To maintain the sleekness of this look, try the Olaplex No.6 Bond Smoother to reduce frizz and maintain shine. If you prefer a straighter look, the GHD Platinum+ Styler will help you achieve those sharp lines. Regular trims are essential for this cut to maintain its blunt structure.

Textured Lob with Side Part

The Textured Lob with Side Part combines volume, texture, and movement for a chic winter look. This cut features medium-length layers that add dimension and a soft, natural wave that works perfectly for all hair types, especially if you’re looking for color ideas for fall or winter. The deep side part adds volume at the crown, which makes this style ideal for round faces, as it adds height and elongates the face.

To keep the texture in your lob, consider using IGK Beach Club Texture Spray or Ouai Matte Pomade to define layers without adding too much shine. Using a light mousse, like Redken Aerate 08, will keep volume at the root without weighing down your hair.

Sleek A-Line Bob

The Sleek A-Line Bob is a stylish and sophisticated hairstyle that works perfectly for winter. This cut is slightly shorter in the back, gradually lengthening toward the front, creating a flattering angle that enhances your facial structure. It’s particularly great for round faces, as the angular lines create the illusion of length. This shoulder-length bob is usually worn sleek and straight, making it a perfect choice for those who love a polished, professional look.

To maintain the smoothness of this cut, use Kérastase Discipline Fluidissime Anti-Frizz Spray to keep frizz at bay in winter. A flat iron, such as the T3 SinglePass Luxe, will help you achieve that sleek, straight style effortlessly.

Mid-Length Shag with Fringe

The Mid-Length Shag with Fringe brings a retro vibe with a modern twist. This medium-length shag cut features soft, disconnected layers throughout the hair, creating volume and texture, while the fringe adds a playful, edgy touch to frame the face. It’s a highly versatile style that suits both round faces and oval face shapes, adding dimension and movement. The fringe draws attention to the eyes, making it perfect for those wanting to accentuate their features. This hairstyle is a trendy, low-maintenance option for winter 2024.

To maintain the shaggy texture, try using R+Co Balloon Dry Volume Spray for added lift and separation. Additionally, a lightweight leave-in conditioner like Amika The Wizard will keep the hair hydrated and frizz-free, especially in the colder months. Regular trims are essential to maintain the layers and prevent the ends from looking scraggly.

Asymmetrical Lob

For those looking for something bold and modern, the Asymmetrical Lob is a perfect choice. This cut is slightly longer on one side, creating a dynamic and fashionable look that’s ideal for round faces. The asymmetry adds interest and sharpness, drawing attention away from the jawline and elongating the face. This hairstyle works well with both straight and wavy textures, and can be styled sleek for a sophisticated appearance or tousled for a more relaxed vibe.

To keep your asymmetrical lob looking sharp, use the GHD Helios Hair Dryer for a smooth blowout, followed by a straightening balm like Oribe Straight Away to maintain the sleekness. A light pomade can also be used to define the ends and enhance the asymmetry.

Wavy Shoulder-Length Bob

The Wavy Shoulder-Length Bob is a classic and versatile hairstyle that’s perfect for winter. This style combines loose waves with a medium-length cut, creating a romantic and effortless look. It’s ideal for round faces, as the waves add softness and frame the face beautifully. Whether you’re going for a more casual look or a polished appearance, this bob can easily be adapted to any occasion.

To enhance your waves, try the DevaCurl Wave Maker or Ouai Air Dry Foam, which will help define the natural texture without weighing down your hair. A lightweight serum like Briogeo Farewell Frizz Rosarco Oil will also help maintain shine and reduce flyaways, keeping your waves smooth even in dry winter conditions.

Feathered Lob with Face-Framing Layers

The Feathered Lob with Face-Framing Layers brings a soft, feathered texture to the classic lob. This cut features light, delicate layers that are strategically placed to frame the face, making it perfect for round faces as it adds structure and balance. The feathered ends create movement and airiness, making this style a great choice for winter 2024-2025. This shoulder-length lob can be styled with soft waves or worn straight for a more polished look.

To maintain the softness of the layers, use Kevin Murphy Smooth Again to keep your hair sleek and frizz-free. A round brush blow-dry using T3 Volume 2.5 Round Brush will help achieve the feathered, light texture, giving your lob a voluminous and airy finish.

Medium Cut with Wispy Bangs

The Medium Cut with Wispy Bangs is perfect for those who love soft, feminine hairstyles. The medium length is ideal for easy styling, while the wispy bangs add a light and airy touch, framing the face without being too heavy. This style works well for round faces, as the bangs draw attention upwards and create balance. The wispy bangs can be worn straight, slightly tousled, or blended into the rest of the hair for a seamless, natural look.

For maintaining the softness of the bangs, try using Kristin Ess Weightless Shine Working Serum to keep them light and manageable. A quick spritz of Drybar Triple Sec 3-in-1 Finishing Spray will also add texture and lift, keeping your bangs fresh all day long.

Romantic Shoulder-Length Waves

The Romantic Shoulder-Length Waves is an elegant and timeless option for winter 2024-2025. This hairstyle features soft, cascading waves that fall just above the shoulders, creating a look that’s both feminine and sophisticated. These waves are perfect for adding volume and movement to medium-length hair, making it ideal for round faces as it helps elongate the face shape. Whether you’re attending a winter wedding or a festive gathering, these romantic waves will complement any occasion.

To enhance the natural flow of the waves, use a lightweight mousse like Kenra Volume Mousse Extra 17, which adds hold without making the hair stiff. To maintain the waves’ soft texture, finish with Gisou Honey Infused Hair Oil for a glossy, frizz-free look. Regular trims will ensure your waves stay bouncy and fresh throughout the season.

Straight Lob with Blunt Ends

The Straight Lob with Blunt Ends is a sleek and polished option for those who prefer a more structured look. This hairstyle features a straight, medium-length cut that ends bluntly, creating a sharp, clean line. The straight lob is versatile and low-maintenance, making it perfect for anyone with naturally straight or manageable hair. This shoulder-length style is flattering for round faces, as the blunt ends provide definition and balance. It’s a chic, professional look that can easily transition from day to night.

To maintain the straight, sleek finish, use Kérastase Discipline Keratine Thermique Blow Dry Primer, which will help protect the hair from heat styling while keeping it smooth. A flat iron like the Dyson Corrale will help you achieve the perfect straight look without damaging your hair.

Mid-Length Bob with Balayage Highlights

The Mid-Length Bob with Balayage Highlights offers a beautiful blend of color and style, making it a top trend for winter 2024. The balayage technique allows for a natural, sun-kissed effect that adds depth and dimension to a classic bob. This hairstyle is particularly flattering for round faces, as the bob’s shape adds definition, while the highlights bring light and movement to the hair. Whether you go for warm caramel or cool ash tones, this cut is versatile and works well with various hair colors.

To keep the balayage vibrant, use a color-protecting shampoo like Pureology Hydrate Shampoo and follow up with Redken Color Extend Magnetics Conditioner to lock in the color and keep it from fading. A touch of Moroccanoil Treatment will keep your highlights shiny and frizz-free, even in the dry winter months.

Shaggy Lob with Choppy Bangs

The Shaggy Lob with Choppy Bangs is perfect for those who want an edgier, more playful look this winter. This cut features uneven, textured layers throughout the lob, combined with choppy bangs that add a rebellious and modern touch. The layers create movement and volume, making this style ideal for round faces as it adds structure and dimension. The shaggy lob is versatile and can be styled messy for a laid-back vibe or slightly more polished for a chic, undone look.

For styling, try using Ouai Texturizing Hair Spray to define the layers and add volume. If you want to enhance the shaggy texture, Bumble and Bumble Surf Spray will give your hair that perfect windswept finish without looking too messy.

Textured Shoulder-Length with Layers

The Textured Shoulder-Length with Layers is a beautifully layered cut that adds depth and movement to medium-length hair. This style features soft layers throughout the hair, creating a voluminous and textured look that’s perfect for winter. The layers are particularly flattering for round faces as they provide shape and elongate the face. Whether worn straight, wavy, or tousled, this cut is versatile and easy to style for any occasion.

To keep the texture in place, use Verb Volume Dry Texture Spray, which adds instant lift and texture. For soft waves, try Drybar The Wrap Party Styling Wand to achieve loose, natural waves that highlight the layers. Regular trims will keep the layers defined and prevent split ends.

Classic Lob with Side-Swept Bangs

The Classic Lob with Side-Swept Bangs is a timeless style that never goes out of fashion. This medium-length cut features a sleek, straight lob with soft, side-swept bangs that gently frame the face. Perfect for those with round faces, the side-swept bangs create an elongated effect, while the straight lob maintains a structured, clean look. It’s a highly versatile hairstyle, ideal for both casual outings and more formal winter events.

To keep the side-swept bangs smooth and frizz-free, try using Oribe Straight Away Smoothing Blowout Cream. A finishing touch of Living Proof No Frizz Humidity Shield will protect the hair from moisture and keep the bangs in place throughout the day. Regular trims will ensure the lob stays sharp and the bangs remain well-shaped.

Curled Lob with Deep Side Part

The Curled Lob with Deep Side Part brings volume, curls, and drama to the traditional lob. This hairstyle features a deep side part that adds height and interest, while the loose curls create a soft, romantic look. This style is perfect for round faces, as the side part and curls add vertical lines, elongating the face. It’s a great choice for those who want to add movement and texture to their medium-length hair while still maintaining a polished appearance.

To enhance your curls and keep them defined, use DevaCurl Light Defining Gel for soft hold without the crunch. For added shine and frizz control, finish with Ouidad Shine Glaze Serum, which will keep your curls glossy throughout the winter months.

Sleek Lob with Center Part

For those who prefer a minimalist, polished look, the Sleek Lob with Center Part is a must-try for winter 2024. This cut features a straight, medium-length lob with a sharp center part, giving off a sleek and sophisticated vibe. Ideal for round faces, the center part creates symmetry and elongates the face. This hairstyle is perfect for both work and evening events, offering a clean, modern look that’s always on-trend.

To maintain the sleekness of this style, use Redken Frizz Dismiss Smooth Force Lotion Spray to keep the hair smooth and frizz-free. For added shine, finish with Kérastase Elixir Ultime Oil Serum, which will give your lob a glossy, polished finish.

Shoulder-Length Cut with Beach Waves

The Shoulder-Length Cut with Beach Waves brings a relaxed, effortlessly chic vibe to the winter season. This style features soft, natural waves that add texture and movement, creating a casual yet stylish look. The beach waves work well with shoulder-length hair, offering the perfect balance of length and texture. This hairstyle is ideal for round faces, as the waves create the illusion of length and soften the jawline, adding a flattering effect to the face shape.

To maintain these carefree waves, use Bumble and Bumble Surf Spray, which enhances texture without weighing the hair down. For added moisture and shine during the dry winter months, Olaplex No.7 Bonding Oil is a great choice to keep the hair hydrated and frizz-free.

Layered Medium-Length Cut with Subtle Highlights

The Layered Medium-Length Cut with Subtle Highlights adds dimension and depth to your look. This style features soft layers that fall naturally, giving the hair movement and volume, while the subtle highlights add a touch of brightness. The highlights are strategically placed to catch the light and enhance the texture of the layers. This style is perfect for round faces, as the layers create the appearance of added height and shape, elongating the face.

To keep the highlights looking fresh and vibrant, use a color-safe shampoo like Matrix Total Results Keep Me Vivid Shampoo. Pair it with Amika The Wizard Detangling Primer to ensure the layers stay soft and manageable.

Textured Lob with Curtain Fringe

The Textured Lob with Curtain Fringe brings volume, texture, and a retro vibe to winter 2024. The textured lob features soft, tousled layers that add depth and movement, while the curtain fringe frames the face perfectly. This style works wonders for round faces, as the fringe helps elongate the face, while the texture adds volume and interest. It’s a versatile cut that can be styled straight, wavy, or somewhere in between.

To maintain the fringe and the texture, try R+Co Balloon Dry Volume Spray for added lift at the roots. For a light hold that keeps the layers in place without weighing them down, Oribe Superfine Hair Spray is a great option.

Medium Bob with Voluminous Curls

The Medium Bob with Voluminous Curls is a bold and beautiful option for those with naturally curly or wavy hair. This cut is designed to enhance the volume and shape of the curls, creating a bouncy, full-bodied look. It’s particularly flattering for round faces, as the curls add height and balance to the face shape. This hairstyle is perfect for winter, adding both warmth and style to your look.

To define and control the curls, use DevaCurl SuperCream Coconut Curl Styler, which adds moisture and hold without making the hair crunchy. A diffuser attachment for your hairdryer, like the Dyson Supersonic Diffuser, will help enhance curl definition while maintaining volume.

Medium Cut with Long Bangs

The Medium Cut with Long Bangs is a sophisticated, modern hairstyle that’s perfect for winter 2024-2025. The medium-length cut keeps things simple and classic, while the long bangs add a touch of drama and style. The bangs are typically side-swept or parted in the center, framing the face and adding softness. This cut works well for round faces, as the long bangs create vertical lines that elongate the face shape.

To keep the bangs sleek and frizz-free, use OUAI Leave In Conditioner, which provides moisture and protection. For added shine and smoothness, finish with Moroccanoil Treatment Light, ensuring your bangs stay glossy all day.

Shoulder-Length Cut with Blunt Bangs

The Shoulder-Length Cut with Blunt Bangs is a bold, structured style that commands attention. The blunt bangs create a strong, graphic line across the forehead, contrasting with the soft, shoulder-length cut. This hairstyle is perfect for those with round faces, as the blunt bangs add an edge, while the shoulder-length cut keeps things balanced and flattering. It’s a chic, modern look that works well for both casual and formal settings.

To keep the bangs in place, use L’Oreal Paris Elnett Satin Hairspray for a flexible hold that keeps your hair smooth without stiffness. A shine spray like Bumble and Bumble Bb.Shine On (and On) Finishing Spray will add a glossy finish to the blunt ends.

Soft Layers with Swooping Bangs

The Soft Layers with Swooping Bangs is a romantic, feminine style that adds softness and movement to the hair. The layers fall naturally, creating a gentle, flowing look, while the swooping bangs sweep across the forehead, adding a touch of drama. This style is perfect for round faces, as the swooping bangs help to elongate the face and create a balanced look. It’s a great choice for winter, offering a warm, soft style that’s easy to maintain.

For maintaining the softness and flow of the layers, use Kérastase Nutritive Nectar Thermique Blow Dry Primer to protect the hair from heat styling while keeping it smooth. A light serum like Davines OI Oil will add shine and reduce frizz, perfect for keeping your hair healthy during winter.

Winter 2024-2025 brings a variety of hairstyles for medium-length hair, from layered and textured lobs to sleek, structured bobs. Whether you’re looking for something soft and feminine or edgy and bold, there’s a haircut for every style and personality. Share your thoughts below and let us know which winter cut you’re excited to try!