47 Best Women’s Medium Haircuts and Hairstyles for Fall/ Winter 2020

The days of moaning about your hair being in that awkward in between mid-length is over, it started with Jennifer Aniston’s Rachel cut in the 90’s and then Victoria Beckham’s millennium lob, and now medium length hairstyles are one of the most requested haircuts in salons. Gone are the days of long flowing extension filled locks and in is healthy, natural mid length haircuts with sun kissed highlights worn in messy knots and braided updos.

Medium length hairstyles are a popular choice in 2018 because they are so versatile and easy to manage. Whilst some consider chin length hair a safe option because it lacks the drama of a buzzcut or the romance of flowing hair but actually it’s a very diverse cut that can be styled in multiple ways. Medium lengths can range from mid-neck line to shoulder length and offers plenty of styling options from messy buns to romantic waves and bold hair colors. Here we look at 47 great options to update your shoulder length haircut for fall.

47Half Bun

Half Bun medium haircut
Instagram / @khloekardashian

This is a great way to style medium hair that is past its best, without having to tie your hair into a full top knot. The hairstyle is easy to achieve; section off the top of your hair and twist the lengths into a top knot before pining it in place.

46Ribbon Curls

Ribbon Curls medium length hairstyle

This less put together curl is favoured by Victoria’s Secret angel as it looks effortlessly yet sexy on medium length haircuts for women.

Simply wrap your hair flat around the curling barrel, making sure there is no space between the wraps of hair and the barrel. Curl the hair for roughly 10-15 seconds so it sets, then release the curl and let it set in the palm of your hand.

45Halo Braid

Halo Braid Medium Lenght Hairstyle

This is very bohemian looking updo is chic and easy to execute. Part your hair into 2 equal sections from the front to the back, don’t worry about the parting being perfect. Take a small amount of hair from one of your two sections and start Dutch braiding, starting from the nape of your neck and picking up additional hair as you travel. Braid along your hairline until you reach back at your starting point. When you reach the nape of your neck finish the braid with a standard French braid and secure with an elastic. Wrap the end of the braid around your head and secure with bobby pins or hair clips.

44Slicked Down

Slicked Down Medium Lenght Hairstyle

Slicked down or slicked back hair is a big celeb favourite and its hard lines are perfect for making any look high fashion. Spray your wet hair with texturizing spray before blow drying, using a small boar-bristle brush to dry the hair up at the crown of the head. Blow dry the sides back, keeping them smooth, and pin them back. Use a 1-inch ceramic flat iron to smooth your hair, adding oil to keep your locks sleek. Back brush the hair at the front of the hairline to give the crown volume, moulding and shaping height with a fine-tooth comb.

43Plaited Ponytail

Plaited Ponytail Medium Lenght Hairstyle

This plaited take on the ponytail is a great way to take medium length hair from the office to the club. It is important to line up your ponytail to where your cheekbones are, on a diagonal, and brush the hair back. Smooth the hair with a bristle brush until it has no kinks and then secure it.

Take a small section from underneath the ponytail, braid it and then wrap it around the ponytail, and secure it with a couple of pins.

42Full Bodied Lob

Full Bodied Lob Medium Length Hairstyle
Instagram / @OLIVIAMUNN

If you have a shoulder length bob haircut or a lob, try adding volume by combining a root lifter, thickening cream and a blow drying technique. Apply a volume-boosting product to damp hair and blow dry with a round brush to pump it up. From there you can add curls, waves or leave it sleek.

41Soft Beach Waves

Soft Beach Waves Medium Lenght Hairstyles
Instagram / @ROSIEHW

This is generally thought of as the best summer hairstyle, a favourite of the likes of Jennifer Aniston, Blake Lively and Rosie Huntington Whiteley.

This style is so natural and organic yet red carpet ready, and can be achieved while you sleep. Towel dry wet hair and apply a texturizing mousse through your mid-lengths and ends. Separate your hair into sections and braid them, the more braids the tighter the curls will be. Leave it overnight and in the morning release braids, using your fingers to comb out the curls.

40Shaggy Cut

Shaggy Cut Medium Lenght Hairstyle
Instagram / @ALEXACHUNG

Medium length shag cuts are one of the most versatile hairstyles out there. The basis of shag haircuts can be varied so it’s perfect for those who want to grow out a medium haircut and suits all types of hair texture. Experiment with layering hair medium hair with bangs, depending on your texture and highlights to add a dimension to the cut. Bangs will make the cut more modern and waves will give the shaggy cut a punk edge. Shaggy cuts are perfect for people struggling with hair that is too thick or too thin, it can add or decrease volume if cut right. If you don’t want to affect the length of your medium cut add a ton of shorter layers that start at the brow line for that shag effect.

39Brushed-Out Waves

Brushed-Out Waves Medium Lenght Hairstyle

No one has time to keep those perfectly bouncy curls in check, it’s all about the undone lived-in hair. Start with dry hair that hasn’t been washed for a few days and apply dry shampoo. Use a one-inch styler and take a two-inch section of hair, start curling close to the root and curl your hair using a rolling motion. This also works great with a hair straightener. Think about styling your hair up and down rather than in and out. If you use a straightener for this style use fluid motions so the iron never stops in one place, this will avoid kinks.

Let the curls cool to set them in place. Use a fine-toothed comb to brush the bends out of each curl, brushing gently upwards. Now spray with hairspray.

38Ombre Lob

Ombre Lob Medium Lenght Hairstyle

Ombre hair is a coloring effect in which the bottom portion of your hair looks lighter than the top. This is a low maintenance look where your roots are on show and the bottom portion of your shoulder length hair is bleached. Start the lighter hair at ear length, making sure your roots are blended into the lighter color. After bleaching this portion add the color you desire, this could be a rich on-trend burgundy or a bold pastel.

37Caramel Highlights

Caramel Highlights Medium Lenght Hairstyle

Caramel highlights are a great way of going lighter without going fully blonde. Caramel highlights will add a natural-looking warmth to brunettes, it can be done with foils or through balayage. The caramel color should be unevenly disturbed so it mimics what the sun does naturally. This is a great way to add dimension and give the illusion of thickness.

36Sleek Centre Part

Sleek Centre Part Medium Lenght Hairstyle

The sleek centre part has really come back into fashion, a favourite of the likes of Kendall Jenner and Gwen Stefani. It’s an easy way to add sleekness to frizzy locks. The secret to creating the super sleek centre part is to use a comb when blowing drying instead of a brush. Brushes can’t get as close to the scalp as a comb, using this tool will help the style last longer. The comb will provide tension and the high heat of the blow dryer will reform the hair’s bonds to make your hair lose any frizz.

35Feathery Lob

Feathery Lob Medium Length Hairstyle

Feathering is a haircutting technique that shapes the ends of the hair while creating variable lengths through the hair. This haircut is perfect for those women who want to get up and go in the mornings, without spending too much time styling the hair. Ask your hairdresser to hold the scissors at a 90-degree angle and move in a fan-like motion, cutting in a slightly V shape. This works great as a mid-length lob that sits at the shoulders but still has texture and movement.

34Fading Roots

Fading Roots Medium Length Haircut

This is a very natural, low maintenance look, all it takes is a little bit of blending. Tap color into the roots and blend them naturally into the lengths. This will give a subtle grow out effect and will prevent separation lines. Choose a tone that is darker than the rest of the hair, it doesn’t have to be traditional brown and blonde it could be something crazier like violet and eggplant purple. Using a semi-permanent color on the root will avoid a band of dark color when your real roots grow out.

33Flipped Out Ends

Flipped Out Ends Medium Length Hairstyle

A favourite since the 60’s the flipped out ends has made a big comeback on recent red carpets, a favourite of Rihanna and Vanessa Hudgens. If your mid length hair already suffers from flipping out, embrace it! The easiest way to give your hair flipped out ends is to use a one-inch curling iron and curl the hair out in segments. To make it last longer apply styling gel to towel dried hair and then blow dry the hair, using a round brush to turn the hair outwards and then use a curling iron for extra effect.

32Glass Hair

Glass Hair Medium Length Hairstyles

Glass hair is the Asian hairstyle trend we have been seeing on celebs in 2018. Start with taking ultra-fine sections of your hair and flat ironing them. Make sure to brush the hair on top of the iron and then pull them down. Finish near the roots and flatten the hair at the top of the head. After straightening, run oil through the ends of the hair and then spray a hairbrush with hairspray, before brushing it through the ends.

31Long Layers

Long Layers Medium Length Hairstyle
Instagram / @GOOHYUN.ANN

Long layers have a bad reputation thanks to the 90’s obsession with getting hair like Jennifer Aniston. 2018 has made layers cool again, it’s all about texture and less about that mushroom shape. The key to acing long layers as a medium length hairstyle is to ask your hairdresser for long layers that are invisible.

If you have thick hair long layers look great on mid-length cuts, the layers should meld cohesively without appearing choppy.

30Tiger Eye

Tiger Eye Medium Length Hairstyle

This stunning and unique shade features a mix of honey, amber and soft brown, all applied with a balayage technique. This color is warm and subtle, giving hair natural sun-kissed tones and eye-catching dimensions. This color combination is great for low maintenance girls as any growth can be worked into it. This will suit all skin tones and looks amazing styled into natural beach waves.

29Blunt Lob

Blunt Lob Mediul Length Hairstyle

Blunt refers to the hair being cut at the same length all around, it’s clean, fresh and youthful. If your hair is naturally thick your stylist can do the blunt cut internally, this will remove the bulk without losing the blunt lob effect. Cut at an angle to keep the mid length cut’s movement. Blunt cuts are also perfect for people who have damaged hair, the straight cut with remove the straggly ends.

28Undone Ringlets

Undone Ringlets Medium Length Hairstyle
Instagram / @MARTINA_HMU

If you’re looking for a glamorous yet easy hairstyle for medium length hair, create undone ringlets. Prepare your hair with a curl spray, this will create long-lasting curls that can survive being undone. Place 1-2 inch sections of your hair between curlers and curl. Using a dressing brush to lightly brush the hair, to loosen the ringlets out.

27Messy Bun

Messy Bun Medium Length Hairstyle

Buns are classic and timeless but in 2018 the bun is worn in an easier, laid-back way. Start by brushing your hair carefully and then use either dry shampoo or texturizing spray.  Create a high ponytail on the crown of the head and divide it into two sections before using your fingers to twist the hair around into a bun, then secure with a hair elastic. To make it look messy pull out a few strands to loosen the look and add volume. To play around with the shape use bobby pins to add dimension.

26Copper Hair

Copper Hair Medium Length Hairstyle
Instagram / @ZOEYDEUTCH

Also known as auburn, copper hair is one of the hottest trends for fall 2018. There are different shades of copper hair, from strawberry to penny copper, that will suit different skin tones. Women with pink undertones will look amazing with pure copper hair, if you have warm toned skin try warmer bronzy copper tones and dark skin tones are more suited to coppers with touches of ruby and violet to them.

25Side Braid

Side Braid Medium Length Hairstyle
Instagram / @DEFTIG_HAIR

A side braid is an interesting take on a braid, it looks much easier and relaxed. Pull your hair over to one side using a tail comb to create a deep side parting. Take a large section of hair from the front of your head and divide it into 3 sections of equal size and begin braiding.  Create one regular 3 strand braid before picking up additional hair as your wave. This braid needs to go around the back of your head and to the opposite side to where you started to braid. To hide the hair band, take a section of hair and wrap it around the end of the braid. For a fuller, messier looking braid pull it from either side to create a thicker appearance.

24Voluminous Bun

Voluminous Bun

If you struggle fitting your medium length wavy hair into a sleek ballerina bun try the looser voluminous bun. Comb through your hair using your fingers and then pull it into a secured, tight high ponytail. It doesn’t matter if there’s flyaways or hair outside of the bun. Spray hairspray onto a comb and tease the ponytail throughout. Wrap the teased ponytail around the hair tie, making sure all the pieces are swept around the tie. Secure the bun with bobby pins and hairspray.

23Half Up Ponytail

Half Up Ponytail Medium Length Hairstyle

The half up ponytail is the favourite red carpet IT girls from Blake Lively to Bella Hadid. Tread carefully with this look as when done wrong can make you like a kindergartener.

To get it looking chic start with texturized hair, the more volume at the roots the better. Keep the style loose to keep it modern and don’t pull all the top sections of your hair back. Section your hair off at the temples, if you have fine hair pull the top section back into a triangle shape and gather more strands. Tease your hair to keep it not looking to prissy.


Asymmetrical Medium Length Hairstyle

An asymmetrical haircut is eye-catching, innovative and will always look cutting edge. Asymmetrical means one side is longer than the other, from lobs to medium length curls there is an asymmetrical option for everyone. Asymmetrical cuts give your face elegant angles and suits all different face shapes.

Bring dimension to thicker hair with asymmetrical medium length layers, this will make your hair feel much less weighty and dragged down. Pin-up curls cut in a subtle asymmetric style look like the epitome of Old Hollywood glamor yet still look modern and fresh. Lobs are very flattering and interesting when cut in an asymmetrical shape.


Balayage Medium Lenght Hairstyle
Instagram / @GISELE

Balayage is a dyeing technique that looks natural, subtle and will work better with regrowth compared to regular foil highlights. Balayage should start close to the root, leading to thicker highlights towards the ends of the hair. To stop the dye looking too harsh apply it to just the surface of the hair instead of saturating throughout. Balayage achieves the natural sun-kissed look by avoiding using foils and instead of performing highlights freehand.

20Pinned Back Bangs

Pinned Back Bangs Medium Length Hairstyle

Growing your bangs out doesn’t have to look awkward. Using barrettes and hair accessories are a great way of getting your bangs out of your face, whether it be for professional or personal reasons. Part your hair how you usually would and then sweep back your bangs until they are up and away from your face. Finish with the hair accessory of your choice.

19Choppy Angled Lob

Choppy Angled Lob Medium Lenght

The lob is a popular and striking medium length hairstyle because it means you don’t have to commit to having a short bob or long hair. The subtle angle keeps things looking refined and elegant, and can be worn with lots of different styles from sleek glass hair to voluminous waves. The angled cut will allow you to ramp up the volume and works great on thick hair.


Feathered Medium Length Hairstyle

Feathered hair gained prominences in the 70’s, designed to look like bird’s feathers it involved layering hair to create a voluminous feathered effect. Feathered hair looks great on all hair types but works well for people who have dense hair as it cuts the bulky heavy hair away from the crown of the head creating wispy ends. The feathering effect is used by holding the scissors at a 90-degree angle and cutting in a V shape. This differs from a medium layered haircut for medium hair by being more invisible, with the feathered ends blending into the hair more.

17Wet Look

Wet Look Medium Lenght Hairstyles

To the untrained eye, this hairstyle may look like you’ve just stepped out the shower but stars like Margot Robbie and Vanessa Kirby are proving it’s a chic and modern evening look.

Style your hair from wet, mix hair gel between your hand and smooth through the whole of your hair, combing your lengths to make sure it is distributed evenly. Avoid using any setting products as this will make the look become crunchy. To fake the wet look, use an old fashion pomade. If you want to add the wet look to a ponytail or updo, dip a tint brush into pomade and paint it onto the desired areas, making sure the area is saturated. Pomade is strong enough to work on even the coarsest of hair.

16Slicked Back Pony

Slicked Back Pony Medium Lenght Hairstyle
Instagram / @EMRATA

This is an incredibly popular runway look, maybe because it’s simple but looks very dramatic and powerful.

Start by flat ironing your hair from roots to tips, making sure you have eliminated any flyaways. Apply a light gel to your hairline. Use a smoothing brush to create a flyaway free ponytail. Add more gel if you find you can’t get the desired slick look. Once your hair is secured in your hand, go back over the ponytail using a fine tooth comb, getting close to the scalp. Use an elastic to tightly secure your pony.

15Grey Ombre

Grey Ombre Medium Lenght Hairstyle

Silvery grey ombre hair is really big on Instagram, mainly due to how it suits every skin tone and hair texture. Because it’s an ombre style, dark at the top and graduating to light, the effect is laid back and easy to wear. This is an easy yet edgy look to achieve if you have naturally dark hair but if you are fair-haired you will need to darken your base. The bottom part of your shoulder length hairstyle could be bleached and then dyed a silver grey, a bluer-toned grey or a violet.

14Finger Waves

Finger Waves Medium Lenght Hairstyle
Instagram / @EMMAROBERTS

The heavily gelled finger waves are a staple of 1920’s flapper fashion and was later brought back by 90’s rappers, now finger waves have reappeared only this time they are much softer.

Use a fine tooth comb on freshly washed hair and create a deep parting before drying. When the hair is totally dry split it into several sections and curl the hair in one direction facing forwards. When completed brush out the curls to transform them into loose waves. If you have thinner hair pin the hot waves flat against your head with duckbill clips and let them cool.

13Front Flip

Front Flip Medium Lenght Hairstyle
Instagram / @AMBERHEARD

The 90’s inspired front flip is so easy that most of us achieve the look unintentionally. This look required hair to be curly or wavy, it only works with something that has a little bend. This style looks best on old hair that hasn’t been washed in 2 or 3 days and apply texturizing spray if you have flat hair. Flip your head over when you’re blow drying the roots, setting the dryer on a low speed and medium heat. Avoid brushing your hair whilst blow-drying as this may flatten the strands.

12Face Framing Layers

Face Framing Layers Medium Lenght Hairstyle

Adding face framing layers is a perfect way to update a medium hairstyle for women, it takes away weight but makes your hair have more movement. Blending soft face framing layers will draw attention to your eyes and can give limp hair movements. If you have a wide forehead and don’t want to draw too much attention to your face add have bangs.

A modern way of incorporating this medium layer haircut into updos is to separate the short layers of hair before creating a ponytail or bun. Wrap them around a curling iron for a few seconds to create a natural looking soft wave before tucking them behind your ears.

11Tuxedo Braid

Tuxedo Braid Medium Lenght Hairstyle

This braided updo looks complicated but if you can achieve French braiding upside down on medium length hair you can achieve this look. Create a square section on your crown and make a ponytail, section out your sides and make more ponytails.

Flip your hair upside down and start a Dutch braid with the middle section until you reach the middle ponytail, tie the ends and incorporate it into the middle ponytail. Start French braiding with the side two ponytails, when you reach the middle ponytail gather all of your hair into a ponytail and make a bun. Tug on the crown to loosen the hair.

10Loose Side Pony

Loose Side Pony Medium Lenght Hairstyle

When you read the term side ponytail it might conjure up 80’s hair nightmares but the side pony is having a much looser comeback. Loosely gather the hair into a low side pony that sits on the shoulder. Leave stands of hair loose so it doesn’t look too put together. Create a deep side part and tease the crown of your hair for a retro side pony that evocates the likes of Brigitte Bardot.

9Shoulder Cut

Shoulder Cut Medium Length Hair

A shoulder cut resembles a bob that has been growing out for a few months. Ask for a blunt cut that falls just above the shoulders but has no layers in it. Thin out the ends with scissors so it looks a little jagged. This cut works with all hair textures and can be worn curly or straight. If you have fine hair, ask for a few face-framing pieces in the front that start just below the eyebrow, for extra texture.

8Wispy Layers

Wispy Layers Medium Length Hairstyle
Instagram / @HAIRBYASLYN

Wispy layers are smooth and soft, and create gradual changes in length. The wispy ends are created by shearing the hair, shearing is when the sharp side of scissors is run down the length and the scissors are turned vertically, slowing chipping away at the ends of the layers. This technique will achieve tapered, subtle ends that will give the hair a flowing movement. Wispy layers look great on side swept bangs.

7Metallic Hair

Metallic Hair Medium Length Hairstyle
Instagram / @SHEISDASH

Metallic hair has been the hottest hair trend for 2018. Metallic dyes get their pigment from metallic salt and will cover greys and give your hair a multi-dimensional look. Metallic hair comes in lots of different forms from romantic rose gold, warm bronzes and icy platinum.

If you have darker hair you may have lighten it with bleach before you can add a light metallic shade but your dark locks will take deep colors like purple and blue, this will give you hair an extra dimension in the light.

6Hairline Braids

Hairline Braids Medium Lenght Hairstyle

This simple hairline braid is a great way to keep your medium length haircut off your face. If you can French braid, then this is great for you but if you can’t this is an easy way to fake it. Grab an inch-wide piece of hair from your natural parting and separate into two pieces. Crisscross the two pieces then add a small section of hair from underneath to the piece closest to your face, this will create a faux braid. Continue this braiding until it reaches behind your ear, then secure it with two bobby pins placed in an X shape. Repeat this on the other side of your parting.

5Curly Hair Pony

Curly Hair Pony Medium Length Hairstyle

Ponytails are one of the easiest yet most versatile hairstyles. Straighten the hair around the hairline and then tease it. Use a band to make a ponytail that sits high on the head and apply gel to calm the flyaways. Use the curling iron to create big bouncy curls after you’ve made the ponytail. Apply hair spray, concentrating on the front section.

4Mermaid Waves

Mermaid Waves Medium length Hairstyle
Instagram / @MINGEY

Mermaid waves are a trademark of stars like Amanda Seyfried and Naomie Harris. Start with creating a centre parting and apply mousse from the middle to the ends of the hair. Use a hair clip to separate this section before you start the curling procedure. Wrap small sections of hair around a clip-less curling iron and curl away from your face, hold the hair to the barrel for five seconds. Remove the clips gentle and brush carefully out the curls so they fall into loose mermaid waves.

3Plaited Bun

Plaited Bun Medium Length Hairstyle

Plaited buns are a chic way to pull the hair away from your face. Tie your hair into a ponytail and secure it loosely at the nape of your neck. Pinch the hair at the crown to add more texture. Braid your ponytail in a classic three-strand braid all the way to the bottom. Make a hole in your hair with your fingers just above the elastic, fold your hair through this hole. Lift your braid with your free hand and bring it to meet your other hand, pulling the braid down through the hole. Fold the braid through again and then flip it through the bulkiest part of the hole, letting the bottom portion of braid fold over on itself. Hold your braid with one hand and use your other to insert bobby pins into the sides.

2Ballerina Bun

Ballerina Bun Medium Length Hairstyle

A ballerina bun is the ultimate classic updo but it’s not as easy to execute as it looks. Smoothly brush your hair back into a ponytail and secure tightly. Wrap the elastic around multiple times as you want it to be tightly secured. Using a comb, hold the ponytail with one hand and comb with the other. Now twist the entire ponytail into a tightrope and start making a bun. Begin wrapping your hair rope tightly around the base of the ponytail, twist it so it’s tight on the crown of your hair. Once your hair is twisted into a bun, tuck the ends neatly into the ponytail base, tucking in any loose ends.

1Looped Ponytail

Looped Ponytail Medium Length Hairstyle
Instagram / @LUNAZ5TH

A looped ponytail is a perfect way to make your ponytail look new and exciting. Create a deep parting and use a shine spray to give your crown a sleek look. Gather your hair into a low ponytail and secure but keep it loose. Slack off the ponytail at the nape of the neck and feed it back through itself and then re-tighten it, this will create a loop shape. Secure any areas with bobby pins if needed and spritz with hairspray.

So instead of rejecting the seasonal shift embrace it by treating yourself to a new hairstyle for medium length hair, color or cut. Don’t be afraid to try new colors, new face enhancing shapes and retro-inspired styles. 2019/2020 is all about messy Meghan Markle inspired buns, deep sleek partings, Hollywood waves and sun-kissed locks.

TrendySeekers was founded by a couple Randy Gardner and his wife, who left their steady jobs to follow their passion of traveling the world. With each passing destination, they discovered new and innovative items used in other parts of the world. A new door opened for them and they decided to make these selected products to every spirited person at reasonable prices. Whether it was creative way to charge phones or modern watches that do much more than just tell time, they decided to bring them all to one platform.