33 Beautiful Cute Winter Hairstyles for Medium Hair

Winter transforms our styling routines, and medium-length hair offers the perfect canvas for creating stunning cold-weather looks.

Whether you’re heading to a cozy café, winter wedding, or snowy weekend getaway, the right hairstyle can elevate your entire appearance while keeping you comfortable and chic.

Medium hair strikes that sweet spot between versatility and manageability, allowing you to experiment with countless styles that showcase your personality.

This comprehensive guide presents 33 beautiful cute winter hairstyles specifically designed for medium hair, featuring everything from elegant braids and romantic waves to practical updos and playful ponytails.

Each style has been carefully selected to complement winter fashion, protect your hair from harsh weather conditions, and ensure you look effortlessly gorgeous throughout the season.

You’ll discover step-by-step techniques, styling tips, and creative variations that work for different occasions, face shapes, and hair textures.

Get ready to transform your winter hair game with these inspiring ideas that prove medium-length hair is the ultimate styling playground for the coldest months of the year.

1. Classic Half-Up Twisted Crown

The half-up twisted crown creates an elegant, romantic look perfect for winter gatherings.

This style combines the sophistication of an updo with the freedom of flowing hair, making it ideal for transitional moments from day to evening events.

Styling Details:

• Take two-inch sections of hair from each side of your head, starting just above your temples
• Twist each section backward toward the crown of your head, keeping the twists tight and secure
• Cross the twisted sections at the back of your head and secure them with bobby pins or a decorative clip
• Gently pull apart the twists to create volume and a softer, more romantic appearance
• Leave the remaining hair down in natural waves or curls for a balanced silhouette
• This style works beautifully with winter accessories like jeweled pins or velvet ribbons

2. Textured Low Bun with Face-Framing Pieces

This effortlessly chic low bun combines sophistication with a relaxed vibe, perfect for winter’s cozy atmosphere.

The face-framing pieces add softness and dimension while the textured finish keeps the look modern and approachable.

Styling Details:

• Begin by applying texturizing spray to add grip and volume to your medium-length hair
• Pull your hair back into a low ponytail at the nape of your neck, leaving out two thin sections at the front
• Twist the ponytail loosely and wrap it around the base to form a relaxed bun
• Secure the bun with bobby pins, allowing some pieces to fall naturally for an undone texture
• Gently pull at the bun to create more volume and a deliberately messy appearance
• Use a curling wand on the face-framing pieces to create soft waves that complement your face shape
• Finish with a light-hold hairspray to maintain the style without stiffness

3. Dutch Braid Ponytail Combo

The Dutch braid ponytail combines athletic practicality with feminine charm, making it perfect for winter outdoor activities or casual weekend outings.

This protective style keeps hair secure while showcasing beautiful braiding technique.

Styling Details:

• Start by sectioning off the top portion of your hair from ear to ear
• Create a Dutch braid (reverse French braid) by crossing sections under rather than over
• Continue the Dutch braid down to the crown area and secure it temporarily
• Gather all remaining hair including the braid into a high or mid-level ponytail
• Wrap a small section of hair around the ponytail elastic to conceal it
• Tease the ponytail slightly for added volume and texture
• This style pairs perfectly with winter sports activities while maintaining style

4. Vintage-Inspired Victory Rolls

Victory rolls bring old Hollywood glamour to your winter style, creating a statement look that’s perfect for special occasions.

This retro hairstyle adds height and drama while celebrating classic beauty aesthetics.

Styling Details:

• Section your hair into three parts: two front sections and one back section
• Apply volumizing mousse to the front sections for better hold and structure
• Take one front section and roll it backward toward your scalp, creating a cylindrical shape
• Pin the roll securely at the base with crossed bobby pins
• Repeat the process on the opposite side, ensuring both rolls are symmetrical
• Style the back section with waves or curls that cascade down
• Set the entire style with strong-hold hairspray to withstand winter wind and weather

5. Messy Side Braid with Ribbon

A messy side braid adorned with ribbon combines bohemian charm with winter whimsy.

This relaxed style works wonderfully for casual gatherings and adds a playful touch to your cold-weather wardrobe.

Styling Details:

• Sweep all your hair to one side, allowing natural texture to show through
• Create a loose three-strand braid starting from behind your ear
• Intentionally leave some pieces out and pull at the braid to create fullness
• Weave a velvet or satin ribbon throughout the braid for winter elegance
• Secure the end with a clear elastic or tie the ribbon into a bow
• Pull out a few face-framing pieces to soften the overall appearance
• This style becomes more beautiful as it naturally loosens throughout the day

6. Sleek Center Part with Tucked Ends

This minimalist style showcases sophistication through simplicity, making it ideal for professional winter settings or modern evening events.

The sleek finish and tucked ends create a polished, intentional appearance.

Styling Details:

• Begin with freshly washed hair and apply smoothing serum while damp
• Create a precise center part using a fine-tooth comb
• Blow-dry your hair straight using a paddle brush and directing heat downward
• Use a flat iron to ensure completely smooth, sleek strands
• Tuck the ends under slightly with the flat iron for a subtle curve
• Apply shine spray for a glossy, healthy-looking finish
• This style works exceptionally well with structured winter coats and tailored outfits

7. Crown Braid with Loose Curls

The crown braid with loose curls creates a fairy-tale princess look perfect for winter weddings or romantic date nights.

This style combines intricate braiding with soft, flowing curls for maximum impact.

Styling Details:

• Part your hair down the middle and create two sections
• Begin a Dutch or French braid on one side, starting at the hairline
• Continue the braid along your hairline like a headband, incorporating hair as you go
• Secure the braid behind the opposite ear with bobby pins
• Repeat on the other side, connecting both braids at the back
• Curl the remaining loose hair with a curling iron in large sections
• Finish with hairspray and add floral pins or crystal accessories for winter sparkle

8. Twisted Low Ponytail

The twisted low ponytail offers an elevated take on a classic style, adding visual interest through simple twisting techniques.

This versatile look transitions effortlessly from office to evening.

Styling Details:

• Gather your hair into a low ponytail at the nape of your neck
• Leave a small section of hair out before securing with an elastic
• Create a small opening above the elastic in the ponytail
• Flip the ponytail up and through the opening to create a twist
• Take the reserved section and wrap it around the elastic to conceal it
• Gently pull at the twisted section to add volume and dimension
• Spray with light-hold hairspray to maintain the structure throughout the day

9. Bubble Ponytail

The bubble ponytail brings playful dimension to medium-length hair, creating an Instagram-worthy style that’s surprisingly easy to achieve.

This trendy look adds volume and interest to a simple ponytail base.

Styling Details:

• Start by creating a high or mid-level ponytail secured with a clear elastic
• Place additional clear elastics down the length of the ponytail at even intervals
• Between each elastic, gently pull the hair outward to create rounded “bubble” sections
• Each bubble should be fuller and more voluminous than the ponytail base
• Continue this pattern until you reach the ends of your hair
• Lightly tease each bubble section for extra fullness and texture
• This style works beautifully for casual winter outings and adds youthful energy to any look

10. Side-Swept Waves with Deep Part

Side-swept waves with a deep part channel old Hollywood glamour while remaining perfectly suited for modern winter occasions.

This style adds drama and sophistication to medium-length hair.

Styling Details:

• Create a deep side part approximately two inches from your natural part line
• Apply volumizing mousse to damp hair for body and hold
• Blow-dry your hair while directing it toward the heavier side
• Use a large-barrel curling iron to create loose, flowing waves
• Brush through the waves gently with a paddle brush for a softer appearance
• Tuck the lighter side behind your ear and secure with decorative bobby pins
• Finish with shine spray and medium-hold hairspray for winter wind resistance

11. Double Dutch Braids into Low Buns

Double Dutch braids transitioning into low buns create an athletic yet fashionable look perfect for winter outdoor activities.

This protective style keeps hair secure while maintaining visual appeal.

Styling Details:

• Part your hair down the center creating two equal sections
• Create a Dutch braid on each side starting from the hairline
• Continue each braid down to the nape of your neck
• Wrap each braided section into a small bun at the base
• Secure each bun with bobby pins and hair elastics
• This style keeps hair protected from winter weather while looking intentionally styled
• Perfect for skiing, ice skating, or any winter sports activities

12. Textured Shag with Curtain Bangs

The textured shag with curtain bangs embraces effortless cool-girl vibes perfect for casual winter days.

This cut-and-style combination works beautifully with medium-length hair’s natural movement.

Styling Details:

• Begin with hair that has natural texture or add texture spray for grip
• Use a round brush while blow-drying to create volume at the roots
• Style curtain bangs by directing them outward and away from your face
• Apply texturizing paste to the mid-lengths and ends for piece-y definition
• Use your fingers to separate and define individual layers
• Scrunch sections randomly to enhance the lived-in, undone texture
• This low-maintenance style embraces winter hair trends with minimal effort

13. Braided Headband with Down Hair

The braided headband with down hair offers a bohemian-romantic aesthetic ideal for winter gatherings.

This style frames the face beautifully while keeping hair out of your eyes.

Styling Details:

• Take a small section of hair from behind one ear
• Create a tight three-strand braid with this section
• Bring the braid across the top of your head like a headband
• Secure the braid behind the opposite ear with bobby pins
• Leave the rest of your hair down in waves or straight
• Add volume to the down section by lightly teasing at the crown
• This style works wonderfully with winter hats that can be worn over the braided band

14. Low Twisted Chignon

The low twisted chignon combines elegance with ease, making it perfect for formal winter events or professional settings.

This sophisticated updo works beautifully with medium-length hair.

Styling Details:

• Gather your hair into a low ponytail slightly off-center
• Divide the ponytail into two equal sections
• Twist each section individually in the same direction
• Then twist both sections together in the opposite direction creating a rope effect
• Wrap the twisted rope around the base to form a chignon
• Secure with bobby pins and add a decorative comb or pin for winter elegance
• Pull out a few soft pieces around the face for a romantic finish

15. Half-Up Top Knot

The half-up top knot balances trendy and practical, keeping hair off your face while maintaining length and volume below.

This versatile style suits casual and semi-formal winter occasions.

Styling Details:

• Section off the top half of your hair from ear to ear
• Gather this section into a high ponytail at the crown
• Twist the ponytail and wrap it around the base to create a knot
• Secure with bobby pins and a hair elastic
• Leave the bottom half of your hair down in its natural texture or add waves
• Pull a few face-framing pieces loose for softness
• This style keeps you comfortable while wearing winter scarves and turtlenecks

16. Waterfall Braid

The waterfall braid creates a cascading, romantic effect that looks intricate but becomes easier with practice.

This stunning style is perfect for winter parties and special occasions.

Styling Details:

• Begin with a side part and take a small section near your hairline
• Start a regular three-strand braid for the first stitch
• As you continue, drop the bottom strand and pick up a new section from the top
• This creates the “waterfall” effect with strands cascading through the braid
• Continue the braid horizontally across the back of your head
• Secure the end with a small elastic behind your ear
• Curl the loose cascading strands for added romance and dimension

17. Sleek Low Ponytail with Wrapped Base

The sleek low ponytail with wrapped base epitomizes minimalist chic, offering a polished look for professional winter environments.

This refined style emphasizes clean lines and intentional simplicity.

Styling Details:

• Straighten your hair completely using a flat iron for maximum sleekness
• Apply smoothing cream to eliminate any frizz or flyaways
• Gather hair into a low ponytail at the nape of your neck
• Secure with a hair elastic that matches your hair color
• Take a small section from the ponytail and wrap it around the elastic
• Pin the wrapped section underneath the ponytail to conceal it
• Finish with shine spray for a glossy, healthy appearance

18. Messy French Twist

The messy French twist updates a classic updo with modern, undone texture perfect for contemporary winter styling.

This look balances sophistication with effortless appeal.

Styling Details:

• Begin by adding texture spray to create grip in your hair
• Gather all hair to one side and twist it upward along the back of your head
• Continue twisting while pushing the hair toward the center
• Tuck the ends into the twist and secure with bobby pins along the seam
• Intentionally pull out sections to create a deliberately messy appearance
• Leave some pieces loose around the face for softness
• This style works beautifully with statement winter earrings and necklines

19. Braided Low Ponytail

The braided low ponytail combines two classic styles into one elevated look perfect for winter’s versatile dress codes.

This style adds visual interest while remaining practical and comfortable.

Styling Details:

• Create a standard low ponytail and secure with a hair elastic
• Divide the ponytail into three equal sections
• Braid these sections together in a traditional three-strand braid
• Secure the end with a small elastic
• Gently pull at the braid to create fullness and texture
• Wrap a small section of hair around the top elastic to conceal it
• Add a decorative hair tie or ribbon at the bottom for winter flair

20. Voluminous Blowout with Flipped Ends

The voluminous blowout with flipped ends channels retro glamour while remaining perfectly wearable for modern winter occasions.

This bouncy style adds life and movement to medium-length hair.

Styling Details:

• Apply volumizing mousse to damp hair focusing on the roots
• Blow-dry hair in sections using a large round brush
• Roll each section around the brush and apply heat before releasing
• Focus on creating lift at the crown for maximum volume
• Use the round brush to flip the ends outward in a classic style
• Set the style with cool air from your dryer to lock in volume
• Finish with flexible-hold hairspray that maintains movement

21. Double Twisted Half-Up Style

The double twisted half-up style creates visual interest through layered twisting techniques, offering an elevated everyday look for winter.

This style combines simplicity with sophistication.

Styling Details:

• Take a small section from one side of your head near the temple
• Twist this section backward toward the crown and secure with a bobby pin
• Repeat this process slightly lower on the same side, creating a second twist
• Mirror this technique on the opposite side of your head
• All four twisted sections should meet at the back center
• Secure all twists together with decorative pins or a small clip
• Leave the remaining hair down in waves or your natural texture

22. Side Fishtail Braid

The side fishtail braid offers an intricate, eye-catching alternative to traditional braiding styles.

This technique creates a unique pattern that’s perfect for winter date nights and special events.

Styling Details:

• Sweep all your hair over one shoulder
• Divide the hair into two equal sections
• Take a small piece from the outer edge of the left section and cross it to the right section
• Repeat on the opposite side, taking from the outer right edge to the left section
• Continue this alternating pattern down the length of your hair
• The smaller the pieces you use, the more intricate the fishtail pattern appears
• Secure at the end and gently pull at the braid to create fullness

23. Pinned-Back Waves

Pinned-back waves create an asymmetrical, glamorous look perfect for winter evening events.

This style showcases your face while maintaining volume and drama.

Styling Details:

• Curl your hair in large sections using a curling wand or iron
• Create waves by alternating the direction of curls
• Brush through the curls gently to create soft, flowing waves
• Take all hair from one side and pin it back behind your ear
• Use decorative bobby pins, jeweled clips, or vintage-style barrettes
• Leave the opposite side full and voluminous cascading forward
• Set with flexible-hold hairspray to maintain the asymmetrical style

24. Braided Crown Updo

The braided crown updo creates a regal, sophisticated appearance ideal for winter weddings and formal celebrations.

This all-up style showcases intricate braiding while keeping hair completely off your neck.

Styling Details:

• Part your hair down the middle creating two equal sections
• Create a Dutch or French braid on each side starting at the hairline
• Continue each braid in a curved path toward the back center
• Cross the braids at the back and tuck the ends underneath the opposite braid
• Secure everything with bobby pins ensuring all ends are hidden
• Pull gently at the braids to create texture and fullness
• Add small floral pins or crystals throughout for winter wedding glamour

25. Textured Ponytail with Volume

The textured ponytail with volume transforms a basic style into a statement look through strategic teasing and texture techniques.

This elevated ponytail works for both casual and dressed-up winter occasions.

Styling Details:

• Tease the crown section of your hair to create height
• Smooth the top layer over the teased section for a polished appearance
• Gather all hair into a mid-level or high ponytail
• Secure with a strong elastic that won’t slip
• Tease the ponytail itself to add fullness and body
• Wrap a section of hair around the elastic base to conceal it
• Use texturizing spray on the ponytail for piece-y, modern definition

26. Loose Gibson Tuck

The loose Gibson tuck offers vintage-inspired elegance with a relaxed, modern interpretation.

This romantic updo works beautifully for winter cocktail parties and semi-formal events.

Styling Details:

• Create a low ponytail but don’t pull hair all the way through on the final loop
• This creates a small loop at the base with ends hanging down
• Take the hanging ends and tuck them up into the loop
• Pin the tucked sections securely inside the loop with bobby pins
• Pull at the style to create fullness and a deliberately undone appearance
• Leave a few pieces out around the face for romantic softness
• This style pairs beautifully with vintage winter accessories and jewelry

27. Twisted Side Swept Style

The twisted side swept style creates asymmetrical drama through simple twisting techniques, perfect for winter date nights.

This romantic look emphasizes one side while keeping hair off your face.

Styling Details:

• Part your hair deeply on one side
• Take the smaller side section and divide it into two pieces
• Twist these pieces around each other creating a rope effect
• Continue twisting while picking up additional hair as you move backward
• Pin the twist behind your ear on the opposite side
• Leave the heavier side down in loose waves or curls
• This style creates beautiful dimension and showcases winter earrings perfectly

28. Space Buns

Space buns bring playful, youthful energy to winter styling while keeping hair completely off your neck.

This fun style works for casual outings, festivals, or creative winter events.

Styling Details:

• Part your hair down the center creating two equal sections
• Gather each section into a high ponytail on each side of your head
• Twist each ponytail and wrap it around the base to create a bun
• Secure each bun with bobby pins and hair elastics
• You can make the buns tight and neat or loose and messy depending on your preference
• Pull out face-framing pieces for a softer appearance
• This style works wonderfully with winter hats that can be worn between the buns

29. Smooth Tucked Bob

The smooth tucked bob creates the illusion of shorter hair while maintaining your medium length.

This sleek style offers professional polish perfect for winter business settings.

Styling Details:

• Straighten your hair completely with a flat iron
• Apply smoothing serum for shine and frizz control
• Create a deep side part for added sophistication
• Tuck the ends under smoothly using the flat iron technique
• The tucked ends should create a curved, bob-like silhouette
• Pin the tucked sections if needed to maintain the shape throughout the day
• This style creates a clean, intentional line that looks professionally styled

30. Braided Ponytail with Wrapped Base

The braided ponytail with wrapped base elevates a simple ponytail through added texture and detail.

This style combines practicality with visual interest for versatile winter wear.

Styling Details:

• Create a French or Dutch braid starting at the crown
• Continue the braid down to where you want the ponytail to sit
• Secure the braid and remaining hair together in a ponytail
• Braid the ponytail itself in a traditional three-strand braid
• Take a small section from the ponytail and wrap it around the elastic
• Secure the wrapped section with a bobby pin underneath
• This creates a cohesive, polished look from top to bottom

31. Romantic Low Side Bun

The romantic low side bun creates elegant asymmetry perfect for winter formal events and weddings.

This soft, gathered style emphasizes femininity and grace.

Styling Details:

• Part your hair on one side and sweep everything to the opposite shoulder
• Gather hair into a low side ponytail at the base of your neck
• Twist the ponytail loosely and wrap it around the base creating a bun
• Secure with bobby pins while allowing some texture to show through
• Pull out soft pieces around the face and at the nape of your neck
• Add floral pins, pearls, or crystals for winter wedding elegance
• This style works beautifully with off-shoulder winter gowns and formal attire

32. Zigzag Part with Sleek Finish

The zigzag part with sleek finish adds unexpected detail to straight, smooth hair.

This modern styling choice creates visual interest through the parting technique alone.

Styling Details:

• Use the pointed end of a tail comb to create a zigzag pattern along your part line
• Make sharp, defined angles as you create the zigzag from front to back
• Straighten your hair completely with a flat iron for maximum sleekness
• Apply shine serum to create a glossy, polished finish
• The zigzag part becomes the focal point of this minimalist style
• Keep the rest of the hair smooth and straight to emphasize the parting detail
• This contemporary style works well with modern winter fashion and clean-lined outfits

33. Faux Bob with Tucked Ends

The faux bob with tucked ends allows you to experiment with shorter hair without commitment.

This clever styling technique creates the illusion of a classic bob while preserving your medium length.

Styling Details:

• Section your hair horizontally at ear level creating top and bottom sections
• Pin the top section up temporarily out of the way
• Take the bottom section and roll it under toward your neck
• Pin the rolled section securely against your head with bobby pins
• Release the top section and smooth it over the pinned bottom section
• The top layer should fall to bob length, concealing the pinned hair underneath
• Style the visible “bob” with a flat iron, curling the ends under for authenticity

Conclusion

These 33 Beautiful Cute Winter Hairstyles for Medium Hair demonstrate that the cold season doesn’t mean compromising your style or creativity.

From elegant updos and sophisticated braids to playful ponytails and sleek straight styles, medium-length hair provides endless possibilities for expressing your personal aesthetic throughout winter.

Each hairstyle in this collection has been chosen specifically to work with medium hair’s unique length while considering winter’s specific challenges like weather protection, hat compatibility, and indoor-outdoor transitions.

Whether you’re preparing for formal winter celebrations, casual weekend activities, or professional work environments, these versatile styles ensure you’ll always look polished and put-together.

The beauty of medium-length hair lies in its adaptability—you can create intricate braided designs that rival longer hair while enjoying the manageability and styling speed that shorter cuts offer.

Remember that healthy hair is the foundation of any beautiful hairstyle, so incorporate proper winter hair care routines including deep conditioning treatments, heat protection, and moisture-locking products to combat the season’s harsh elements.

Experiment with these 33 Beautiful Cute Winter Hairstyles for Medium Hair, adapt them to suit your face shape and personal preferences, and discover which styles make you feel most confident and beautiful during the winter months.

With these inspiring options at your fingertips, you’ll never run out of fresh ideas to keep your medium-length hair looking stunning all season long, proving that winter can be your most stylish and creative hair season yet.