Latest-Hairstyles.com logo What kind of style or color are you looking for?
Now Reading 20 Medium Length Hairstyles for Winter: Our Top Picks!

20 Medium Length Hairstyles for Winter: Our Top Picks!

Check out these 20 amazing medium length hairstyles for winter! You’re sure to find a style that is perfect for you. Whether you’re just hanging out with the girls or attending a fabulous party, there is a mid length style for you this winter season!

1. Jaime

Beautiful soft waves like these soften the face and give a very youthful appearance

medium length hairstyles for winter

How to Style:

1. Work a quarter-sized amount of styling cream through towel dried hair.

2. Blow dry hair with a medium heat setting. Use a paddle brush and a wrapping motion to add movement as you dry.

3.Spray hair with heat setting spray.

4. Curl medium-sized sections of hair with a 1-inch barrel curling iron.

5. Allow curls to cool then lightly tousle.

6. Finish with a soft hold hairspray for a bit of touchable control.

Recommended Products:

Sebastian Shaper hairspray gives a touchable, crushable hold that’s perfect for styles like this.

Best Face Shapes:

All face shapes with hair that is medium in texture and density will suit this hairstyle

2. Cassandra

These elegantly soft curls are swept to one side for a soft and polished finish.

Asymetri-Curl Medium Look Asymetri-Curl Medium Look View 2

How to Style:

1. Wring excess moisture from hair, then apply a quarter-sized amount of styling cream throughout.

2. Part hair to one side.

3. Blow dry using a paddle brush.

4. Use a 1-inch diameter curling iron to create ringlets from mid-lengths to ends. Section hair as you go to make curling easier.

5. Sweep hair to one side and secure with a few bobby pins.

6. Finish with a medium or high hold humidity-resistant hairspray.

Recommended Products:

Kenra’s Styling Creme moisturizes, protects and conditions the hair as you blow dry into into your desired style.

Best Face Shapes:

All face shapes with hair that is medium in texture and density will suit this hairstyle.

3. Scarlett

This lovely long crimson bob is totally dressed up with beautiful, bouncy curls.

Totally Twisted Red Medium Hairstyle For Winter

How to Style:

1. Apply thermal protection to hair.

2. Curl sections of hair around a medium barrel iron.

3. Set with a flexible hold finishing spray.

Recommended Products:

Hot Off The Press protects hair from the heat of the damage while giving it hold that will help the style last.

Best Face Shapes:

Oval face shapes with hair that is medium in texture and density will suit this hairstyle.

4. Kendra

This gorgeous hairstyle is worn smooth from roots to the midshaft and then curled from the midshaft to the ends.

Smooth Medium Hairstyle For Winter with CurlsSmooth Medium Hairstyle with Curls Side

How To Style:

1. Apply thermal protection to hair.

2. Curl the midshaft to the ends of the hair with a medium-sized curling iron.

3. Set with a finishing spray.

Recommended Products:

Hot Off The Press is a thermal protection spray that protects hair from the heat of irons.

Face Shape and Hair Type:

Longer face shapes with hair that is medium in texture and density will suit this hairstyle.

5. Kristin

Who says beachy waves are just for summer?

Medium Hairstyle with Beachy WavesMedium Hairstyle with Beachy Waves Side

How To Style:

1. Apply thermal protection to hair.

2. Wrap sections of hair around a medium barrel curling wand.

3. Mist a texture spray on your hair.

4. Rough up the hair with fingers to create more texture.

Recommended Products:

AG Texture Spray gives hair a textured, moveable finish.

Face Shape and Hair Type:

All face shapes with hair that is medium in texture and density can wear this style.

6. Kristin – Version 2

This gorgeous style starts out with beachy waves, but finishes as seriously amped up beachy waves! It is messy and undone, yet sexy and really on trend.

Sexy Hairstyle with Beachy Waves For WinterSexy Hairstyle with Beachy Waves Side

How To Style:

1. Apply thermal protection to hair.

2. Wrap sections of hair around a medium barrel curling wand.

3. Expand the hair sideways by randomly lifting sections of hair up while spraying a texture spray on it.

4. Once you have expanded the hair a lot, decrease the volume by roughing the hair up with fingers which will also give it more texture.

5. Set the style with a finishing spray.

Recommended Products:

AG Texture Spray gives the hair a lot texture and volume.

Hair Type and Face Shape:

Long face shapes with hair that is medium in texture and density will suit this style.

7. Daisy

This pretty hairstyle features sections of hair curled away from the face and a light teasing in the crown area for added volume.

Medium Hairstyle with CurlsMedium Hairstyle with Curls Side

How To Style:

1. Apply thermal protection spray.

2. Curl sections of hair away from the face using a medium barrel curling iron.

3. Tease the hair at the crown area using a teasing brush or comb.

4. Set the teasing with a firm finishing spray.

5. Set the rest of the hairstyle with a flexible hold finishing spray.

Recommended Products:

Paul Mitchell’s Extra Body Finishing Spray is great at holding up teasing in styles like this one.

Face Shape and Hair Type:

All face shapes with hair that is medium in texture and density will suit this hairstyle.

8. Vivian

These lovely, shiny curls are curled towards the face without covering it.

Dark Medium Hairstyle with CurlsDark Medium Hairstyle with Curls Back

How To Style:

1. Apply thermal protection to hair.

2. Curl sections of hair with a medium barrel curling in towards the face.

3. Set with a finishing spray.

4. Mist a shine spray on the hair.

Recommended Products:

Shine Spray by Kenra Professional is a great way to add shine to the hair without disrupting the style.

Face Shape and Hair Type:

Longer face shapes with hair that is medium in density and texture will suit this hairstyle.

9. Sarah

This haircut is layered shorter in the front and longer in the back. It has a long, side-swept fringe and is styled with the ends flipping out and backwards for a flirty finish.

Layered Haircut with FringeLayered Haircut with Fringe Back

How To Style:

1. Apply a styling product to wet hair.

2. Blow dry sections of hair smooth with a styling brush.

3. Apply thermal protection to hair.

4. Use a flat iron to flip the ends out and backwards.

5. Set the style with a finishing spray.

Recommended Products:

Hold Me Tight is a flexible hold spray with long-lasting hold.

Face Shape & Hair Type:

Longer face shapes with hair that is medium in texture and density will suit this hairstyle.

10. Carrie

This is a trendy long bob styled with its natural curly texture.

Long Bob with CurlsLong Bob with Curls Back

How To Style:

1. Apply a styling product to wet hair.

2. Scrunch hair to encourage curl formation.

3. Use a diffuser to dry hair completely.

4. Apply a small amount of pomade by scrunching it into your hair for hold.

Recommended Products:

Grooming Pomade is a high-shine pomade by Paul Mitchell that gives curls shine and hold.

Hair Type and Face Shape:

Longer face shapes with hair that is naturally curly will suit this hairstyle.

11. Susan

This long layered bob is shorter in the back and longer in the front. The extreme side parting causes the heavier side to appear heavily layered and the lighter side to be not as much, creating a fashionable finish to this winter-perfect style.

Long Layered BobLong Layered Bob Side

How To Style:

1. Apply thermal protection to hair.

2. Smooth sections of hair with a flat iron, slightly beveling the ends.

3. Apply a shine serum.

Recommended Products:

Gloss Drops by Paul Mitchell will give the hair a luminous and frizz-free finish.

Face Shape and Hair Type:

Wider face shapes with hair that is medium in texture and density will suit this hairstyle.

12. Chloe

This mid length hairstyle features tight ribbons of curls curling away the face.

Medium Hairstyle with Tight CurlsMedium Hairstyle with Tight Curls Side

How To Style:

1. Apply thermal protection to dry hair.

2. Curl sections of hair away from the face using a small barrel iron.

3. Apply a product for shine.

4. Set the style with a finishing spray.

Recommended Products:

Shine Spray by Kenra Professional allows you to add shine to hair without disrupting the style.

Face Shape & Hair Type:

All face shapes with hair that is medium in texture and density will suit this hairstyle.

13. Amy

This hairstyle is curled only towards the ends of the hair with the curls curling away from the face. It is teased in the crown area for volume and a trendy finish.

Medium Hairstyle with Volume and CurlsMedium Hairstyle with Volume and Curls Back

How To Style:

1. Apply thermal protection to dry hair.

2. Curl sections of hair away from the face using a medium barrel iron. Curl only the middle to the end of each section.

3. Tease the hair at the crown using a comb or teasing brush.

4. Set the style with a finishing spray.

Recommended Products:

Hot Off The Press is a thermal protection spray that protects hair from the heat of irons.

Face Shape & Hair Type:

Wider face shapes with hair that is medium in texture and in the density will suit this hairstyle.

14. Justine

This sleek haircut is primarily one length, but is slightly longer in the back than it is in the front.

One Length Straight HairstyleOne Length Straight Hairstyle Side

How To Style:

1. Apply a styling product to wet hair.

2. Blow dry sections of hair smooth with a styling brush.

3. Apply thermal protection to hair.

4. Smooth hair even more with a flat iron.

5. Apply a product for shine.

Recommended Products:

Sculpting Foam is a conditioning foam that is helps really well in creating great blowouts.

Face Shape & Hair Type:

Wider face shapes with hair that is low in density and with texture that is fine to medium will suit this hairstyle.

15. Kelsey

This winter-perfect bob is so lightly layered that it’s almost one length.

Lightly Layered BobLightly Layered Bob Side

How To Style:

1. Apply a styling product to wet hair.

2. Blow dry sections of hair with a medium to large-sized round brush.

3. Set the style with a finishing spray.

Recommended Products:

Fast Form is a cream gel that allows you to sculpt the hair straight, wavy or curly.

Face Shape & Hair Type:

All face shapes with hair that low to medium in density and medium in texture will suit this hairstyle.

16. Amanda

This is a stunning one-length haircut with face framing layers in the front. It is worn with a side part and styled straight with a slight bend at the ends.

Medium Haircut with Face Framing LayersMedium Haircut with Face Framing Layers Side

How To Style:

1. Apply styling product to wet hair.

2. Blow dry the hair smooth with a styling brush.

3. Apply thermal protection.

4. Smooth the hair with a flat iron.

5. Apply a serum for shine.

Recommended Products:

Gloss Drops adds luminous shine and gets rid of frizz for a sleek finish like this style.

Hair Type and Face Shape:

All face shapes with hair that is medium in texture and density will suit this haircut.

17. Sandra

This chic bob is parted to the side and ends a few inches from the chin. It is styled sleek and smooth, making it the perfect look for day or night.

Bob with Side PartBob with Side Part Side

How To Style:

1. Apply styling product to wet hair.

2. Blow dry the hair smooth with a styling brush.

3. Apply thermal protection.

4. Smooth the hair with a flat iron.

5. Apply a serum for shine.

Recommended Products:

Hot Off The Press is a thermal protection spray that has hold. It protects hair from heat and helps the style last longer.

Hair Type and Face Shape:

All face shapes with hair that is medium in texture and density will suit this haircut.

18. Samantha

This beautiful hairstyle starts out smooth at the roots and ribbons into a curl towards the ends.

Medium Hairstyle with Ribbons of CurlsMedium Hairstyle with Ribbons of Curls

How To Style:

1. Apply thermal protection to hair.

2. Starting an inch away from the roots, smooth sections of hair with a flat iron and begin to ribbon the hair into a curl as you reach the ends.

3. Set with a finishing spray.

Recommended Products:

Hold Me Tight is a flexible hold spray that allows hair to have movement and be touchable without a crunchy finish.

Face Shape and Hair Type:

Wider face shapes with hair that is meidum in texture and density will suit this hairstyle.

19. Emily

This long layered, mid length haircut is styled with soft flowy waves.

Long Layerd Medium HairstyleLong Layerd Medium Hairstyle Side

How To Style:

1. Apply thermal protection to dry hair.

2. Curl sections of hair away from the face.

3. Use a dressing brush to brush through the curls and loosen them.

4. Set the style with a finishing spray.

Recommended Products:

Alterna Bamboo Smooth Anti Breakage Thermal Protectant Spray protects hair from heat up to 428 degrees.

Hair Type and Face Shape:

Longer face shapes with hair that is medium in texture and density can wear this look.

20. Sabrina

Sections of hair in this hairstyle are curled in different directions, giving it a more natural look. The hair on top of the head is teased for more volume and a trendy finish.

Medium Hairstyle with VolumeMedium Hairstyle with Volume Side

How To Style:

1. Apply thermal protection spray.

2. Curl sections of hair in different directions using a medium barrel curling iron.

3. Tease the hair on top of the head.

4. Smooth the surface of the teasing with a comb.

5. Set with a finishing spray.

Recommended Products:

Extra-Body Finishing Spray by Paul Mitchell is great at holding up styles like this.

Hair Type and Face Shape:

Wider face shapes with hair that is medium in texture and density will suit this hairstyle.

Beat the winter blahs by keeping your style fun. Treat yourself by grabbing that hot new texture iron you’ve been eyeing and trying something new with one of these cute medium length hairstyles for winter!