Winter Haircuts for Round Faces 2025–2026 Style Guide: 20 Trendy Medium & Long Cuts to Try This Season

The winter is the time when warm sweaters, hot lattees, and some reinvention creep into our daily life. However, the point is that when the weather changes, and the temperature drops, most of us revert to the same hairdo, which is tucked into a scarf, covered by a beanie. What would happen if this winter you hibernated your hair, and instead of being the main character, you gave it the main character?

You are after something sleek, something fun, or simply a new cut that suits your features, the winter hair cuts of round faces that follow are full of inspiration. What do you do to achieve balance and still be soft? What forms appear in the cold winter light that cheekbones? And what cuts are going to be popular in salons in 2025? We can open up the answers.

Soft Volume Bob with Natural Texture

This appearance is a combination of traditional design and contemporary gentleness. The hair is positioned just above the shoulders and is styled into a large bob which encloses the face without being too bulky. It is light, airy, and a bit dishevelled, so it has that lived-in elegance that is so effective on winter hair cuts in medium round faces. The shape cuts the cheeks in a very delicate way and gives the effect of a slight elongation which is so flattering on the round face shapes. Makeup and comfy knitwear are in warm colors, which underlines the atmosphere of the season.

In the case of this type of bob, I would always suggest applying a light-weight volumizing mousse, then blow-drying it with a round brush. A frizz-free diffuser attachment can be used to increase natural movement. The shape is soft yet defined even after hours under a coat collar by a touch of texturizing spray at the end.

In my case, this haircut is the wear and go haircut. It is smooth yet not overly smooth and this is what I want on cold mornings when I am in a hurry to grab a cup of coffee. This is the sort of appearance that celebrity hairstylist Kristin Ess frequently discusses the need to keep moving in bobs, and this is precisely such an appearance, arranged but never rigid.

Chic Shaggy Bob with Modern Bangs

This is where it becomes a little more daring. This medium length cut has gently overlaid ends and contemporary sweeping bangs across the forehead. It is an excellent choice of winter haircuts medium round faces, which adds structure to the top and the lower part is loose and playful. The combination of colors cool brown with soft blonde accents adds an additional dimension to this cut, which suits the dim winter light.

To maintain it, I typically use a mild sulfate-free shampoo and a hydrating mask once a week, particularly when it is heating season and the air inside becomes dry. One of my favorites is the All Soft Heavy Cream Hair Mask by Redken, which replenishes the moisture and prevents the bangs to frizz out at any moment.

Personally, I am a fan of this cut changing with the style. Toss it straight or scrunch it with a sea salt spray to achieve a French or an undress look respectively. It makes round faces look fresh and lifted without making too much effort. Gregory Patterson once said that this kind of bang can make the face look different, and, frankly, he is correct in this respect, they make the attention go up in such a flattering manner.

Warm Brunette Layers with Face-Framing Highlights

This fashion falls between classic and fashionable. The brushes are long enough to go beyond the chin, and the layers are soft and blend well. The most notable thing is the positioning of face-framing highlights – the lighter strands around the front make the complexion lighter and create the illusion of added structure. It is one of the most classy winter hair cuts round face hairstyles to those who prefer to look presentable without being too styled.

I believe that a sleek blowout miracles this appearance, and even a small curve at the ends is charming. When you have hair that easily loses volume in the winter, it is a game changer to apply a root-lifting spray before you dry your hair.

In my experience, face-framing is the hidden ingredient to this cut popping. They lighten the features, particularly when the winter sun strikes at the right time. And the warm brunette base? It is such a good match with warm neutral knits and natural colors this season.

Effortless Center-Part Medium Cut

Simplicity can be a very eloquent thing. This is a gorgeous understated medium length haircut with a clean center part. The layers are light, the finish is natural and the overall shape stretches the face elongating it in a gentle manner, which makes it an ideal haircut in winter with medium round faces. The warm bronde colors running through the hair are not overwhelming.

The cut is my winter essential when it comes to a lightweight leave-in conditioner. It does not flatten the strands but leaves them smooth. In addition, when the hair is still wet, it is better to brush it to maintain that in the middle part.

The thing I like about this appearance is that it is versatile. You can stick it behind your ears to have a clean look or leave it to fall freely to have a soft look. It makes me think of the smooth cuts that you find in coffee shops in cold mornings – useful, slimming and nonchalantly stylish.

Classic Sleek Bob with Side Part

A sleek bob with a deep side part is something that is timeless. This is a cut that is at the level of the chin, slightly angled to move and it is one of the cuts that will be used in 2025 in round face winter haircuts. The gloss, the smooth edges, the assertive figure – it is a cut that does not require much to create an impression.

I prefer to brush this style using a paddle brush and a heat protectant serum and then flat iron it in small sections. It is not to overdo it, you want that natural swing. A spritz of shine at the ends provides that fresh salon look, but is not heavy.

This cut is an immediate definition to anyone with a round face shape. The side section gives the impression of length and balances the roundness very well. It is the type of haircut that goes with winter coats just as much as it goes with a statement lip.

Layered Curtain Bangs with Flowing Length

Layered curtain bangs with flowing lengths and round face shapes are few styles that can make the softness of the face shape shine. The forehead is softly framed by the bangs which open up the features and the long tapered layers are cascading down which visually lengthens the face. It is a contemporary but old-fashioned style that is just perfect in the category of winter haircuts long round faces, providing balance, movement, and a bit of romanticism. This outfit is paired with a plain black turtleneck and gold accessories, which create the impression of city chic with ease.

For winter, hydration is key. I prefer using a lightweight hair oil at the mid-lengths and ends to ensure that they are not heavy and greasy. A large-barrel curling iron on a gentle wave makes the layers shine through, and a soft-hold hairspray does not make it stiff.

The thing I love about this cut is that it balances between refined and unpolished. Curtain bangs can soften strong features and still frame the face, and that is why this look is so effective with round face shapes, as it is often discussed by celebrity stylist Anh Co Tran.

Textured Blonde Bob with Side Sweep

This is a medium round face textured blonde bob that is one of the best winter haircuts. The asymmetry is formed by the side-swept styling which lengthens the face. The waves are loose, natural and not puffed, and the creamy blonde shade illuminates gray winter days like a ray of sunlight at the right time. The slightly off-centered aspect gives it motion and prevents the cut to be too rigid.

To preserve the blonde shade during winter, I would always suggest the use of a nourishing shampoo mixed with a purple toning shampoo to prevent the appearance of brassiness. A moisturizing mask should be used at least once a week to keep the color bright and the texture soft.

In my case, this type of bob is the right combination of polish and play. It is work friendly and yet entertaining enough to make plans on weekends. Its framing of the cheekbones is particularly flattering on round faces, which creates the illusion of more structure.

Luxurious Long Layers with Subtle Highlights

Long layers are an old standby. This style is very easy to move along the shoulders, and there are soft waves and light caramel-coloured highlights that are interwoven. It is one of those winter hair cuts round faces that is long and hits the perfect balance between the grace and the nature. The highlights give the hair a dimensional quality, and it appears to be rich and multidimensional even in low winter light.

I usually use a light heat protectant in my daily routine and a big curling wand to add these soft bends. The effect is achieved by brushing the curls out with a wide-tooth comb afterward. It is an excellent fit when you are in need of a glamorous and feminine figure that would fit a round face.

Whenever I have a similar style on, I can see how it immediately lifts my outfit, even when I am simply wearing a warm cream blouse. It is smooth yet not flashy – just the right thing to wear on winter evenings.

Casual Blonde Waves with Middle Part

This appearance is what winter cool is all about. Medium length cut with smooth textured ends, a center section and beachy blonde waves. It is a flexible choice in medium round face winter haircut, and it is very good with a rounder face, as the waves part around the cheeks, and they gently shape the face.

I prefer to spray the wet hair with a salt spray, squeeze it and leave it dry naturally to achieve that carefree feel. When necessary, I use a curling wand to add a more refined look to some of my pieces. It is the type of style that would be nice to peep out of a beanie or even with layered jewelry and a denim jacket.

It possesses this young, fresh air that is ideal on casual winter days. It is not making too much effort but it makes an impression – which is what a good haircut ought to do.

Fiery Copper Medium Cut with Full Fringe

This daring copper haircut shows that winter is the season when it is better to welcome warmer colors. The medium length waves combined with a full, slightly curved fringe give it a very impressive silhouette making it one of the most statement-making winter haircuts round faces looks of the season. The copper shade illuminates pale winter skin and brings an immediate personality to any wardrobe.

It takes some additional attention to keep red colors lively in winter. To ensure that pigment is locked in, I apply color-safe shampoos and cold water rinses. A glossing treatment at regular intervals of few weeks keeps the copper looking fiery rather than faded.

I have always thought that a bright hair color and a traditional cut make the most memorable appearance. This mix of plush copper and full bangs exudes that editorial swagger without being too much. It is cozy, light-hearted, and completely memorable on the round face shapes.

Ginger Bob with Subtle Layers

This spicy ginger bob is a winter showstopper. This is soft-layered around the ends and this makes it have a delicate structure that is ideal to match the round face shapes. It is very close to the jawline and forms a soft framing effect that stretches the face without severe lines. The cozy copper colors are matched with winter neutrals, and it is one of the best winter haircuts medium round faces in 2025.

In order to maintain this shade during cold months, I use color-depositing shampoos on every other wash and a nourishing mask to combat winter dryness. A swipe with a straightener using low heat also increases the smoothness without destroying the natural texture.

The best part of this haircut is that it has a warm, friendly feel to it, it is fresh, flattering and it looks fantastic with thick sweaters and gold jewels.

Classic Short Bob with Soft Bangs

The round face winter haircuts are given a sophisticated twist with this classic short bob with soft bangs. The bangs are curved and feathery in nature, and they open the forehead providing balance to the face shape. The bob itself is a nice fit at the chin level, which is why it is a good option of any person who desires to have a structured yet feminine winter cut.

This appearance is quite easy to style. I tend to use a round brush to blow-dry the ends and the bangs and use a bit of serum to make it shinier. It can be worn beautifully even in scarves and winter hats.

It is a style with a certain retro appeal that is quite comfortable in snowy urban streets a mixture of old fashioned and fun.

Elegant Side-Parted Bob

Bobs, which are parted on the side, will never go out of fashion and this is a classy one. The profound separation is a touch of drama, and the chin-cutting incision is a beautiful carving of the lower face. On round faces, this type of parting produces immediate elongation, so it is one of my recommendations of round face haircuts in winter to anyone who wants to feel polished.

I prefer a heat protectant and a flat iron to make it look smooth, although a slight bend at the ends helps to make the cut not so harsh. It has a healthy winter glow without frizz achieved by a middleweight serum.

Something about this cut is quietly powerful. It is simple yet stylish – ideal to wear with structured coats or turtlenecks when the weather gets cold.

Retro-Inspired Medium Cut with Curved Fringe

This retro cut is a mix of medium length with a bouncy and curvy fringe and layered ends. The gentle waves provide movement and volume and the bangs draw the attention to the eyes. It is a complimentary option in medium round face winter hairstyles, particularly when you are attracted to romantic yet slightly vintage looks.

To style it, I tend to use a medium round brush to shape the fringe and layers and then apply a light hairspray to ensure that the bounce is maintained. It is the type of haircut that goes well with winter dresses and fine jewelry, giving some glamour to daily life.

This appearance reminds me of the traditional winter movie heroines – tender, self-assured, and easy-chic.

Modern Layered Cut with Contrasting Highlights

It is a contemporary layered cut that is an impressive mix of dimension and motion. The highlighting of the curtain bangs and layers is enhanced by the contrasting cool tones highlights that outline the face and provide depth to the darker base. In case of long round faces in winter haircuts, this is a statement statement which provides length and edge to the softer features.

To keep these contrasting tones in place during winter, it is necessary to apply a toning shampoo to the highlighted areas and a nourishing treatment on the darker base to keep both tones fresh. It is worth it -the outcome is a vibrant high impact appearance that even makes the grayest days brighter.

As an individual, I am fond of the way this hairstyle interacts with light. The manner in which the highlights come out through the curls and layers is so full of character. It is fashionable and yet can be used in daily winter life.

Layered Mid-Length Cut with Soft Dimension

This is a mid length, layered cut that is the epitome of subtle sophistication. The soft layers are used to frame the face without giving it any bulk and it is one of the most flattering winter haircuts long round faces styles of 2025. The caramel shades are soft and warm the skin, and the shape of the whole figure produces a natural lift, which perfectly balances the rounded features.

This appearance is stylishly effortless. I tend to use a light volumizing mousse at the roots, blow-dry with a round brush and finally, a flexible hairspray to fix the movement. It is feminine, soft and matches all winter clothes, including oversized knits and smooth blazers.

This hairstyle is like a cup of coffee on a cold morning: it is simple, fulfilling, and looks stylish so easily.

Dusty Rose Shag with Feathered Layers

This dusty rose shag is all to those who like a playful touch. The feathered layers are amazingly textured, and the curtain bangs soften the shape in general, making it an amazing choice in the winter haircuts medium round faces trends. Even the color, a subdued rose with cool undertones, is such a refreshing change to grey winter skies.

It is sometimes difficult to maintain pastel colors during winter, and I prefer to wash in lukewarm water using sulfate-free color-safe shampoo. A moisturizing leave-in is used to keep the hair soft, particularly at the fringe.

This fashion is rebellious and fashion-forward yet wearable. It is ideal when you wish to be noticed but not too much.

Deep Side-Part Textured Bob in Burgundy

This deep side-part burgundy textured bob is bold, confident and most importantly very flattering to the round faces. The angled section provides immediate structure and the dishevelled ends introduce playfulness. This is one of the haircuts in the winter that round the face, but it has a modern shape and a bright color.

In order to maintain the texture, I rub some styling cream in wet hair and leave it to dry naturally to create a soft, natural wave. A spray that protects the color is necessary to ensure that deep red color does not fade too quickly.

The haircut is so cool-girl, it is an easy-going style and it goes well with statement accessories and a bold lip.

Classic Chin-Length Bob with Sleek Finish

The chin-length bob is always timelessly sophisticated. This one is slick and shiny, and has a slight side part that extends the face and outlines the features in a very precise way. It is one of the best winter haircuts medium round faces that any person would want to have a clean and minimal look, yet it still feels high.

I prefer using a paddle brush to blow-dry my hair and then straighten it with a flat iron to make it shiny and mirror-like. A shine spray is a nice finishing touch that does not make it heavy.

The best thing about this cut is the versatility of it. It always looks good whether you are wearing it to a dinner out or you are putting on layers.

Soft Blonde Layers with Face-Framing Waves

This dreamy blonde cut is a rounding off to the list. The waves are soft and flow around the face making the complexion lighter and the silhouette longer. It is one of those winter hair cuts long round faces that are equally beautiful with or without make-up, light, dimensional and full of movement.

To achieve this soft wave, I tend to spray a heat protectant, part large strands loosely and brush them out. It has a touch of lightweight oil on the ends to make it look healthy and winter-glow.

It is a very classy appearance–it takes the light well, and it suits all kinds of faces, but it suits round faces best, as it has those long face-giving layers.