women over 50 with glasses

30 Fabulous Hairstyles for 50 Year Old Woman With Glasses

A woman should be able to wear whatever hairstyle she wants regardless of her age. Following that train of thought, we are however sometimes at a loss on how to style ourselves in a way which we think are flattering. We search for inspiration high and low. Here, we present to you 30 hairstyles for 50-year-old women wearing glasses in the hopes that maybe we can inspire you too!

1Blonde Pixie

This super cute and practical hairstyle is a definite favorite because it is something we like to call “wash and wear.” It is very low maintenance. If you have a bit of time on your hands, you can put on some product and add a bit of texture here and there.

2Blonde Long Bob

This pretty haircut is flattering for all face shapes. It looks very casual and you can easily style it up or down. It is quite versatile and is very popular among all age groups. You can choose to have it chin length, or a little longer down to your shoulers for a flattering Lob.

3Asymmetrical Bob with Bangs

A nice asymmetrical bob is greatly favored by women with round face shapes as it gently frames the face, giving it angles. Both cat-eye and rectangular glasses suite this face shape.

4Bob with One-sided Undercut

We personally think that sporting an undercut is really cool, as evidenced by this photo. It’s a nice, playful style that shows off your fun side. It is best accessorized with a smile!

5Brunette Lob with a Side Part

This is a lovely hairstyle that doesn’t need a lot of fuss. The color is a beautiful chocolate that flatters most skin tones, and the look is casual and easy.

6Short Layers with Thinned Fringe

This hairstyle is probably the workhorse of hairstyle. Very little maintenance needed, can easily be air-dried, and just all around comfortable. What more can you ask for?

7Tight Top Bun

This power hairstyle speaks pure business. It is neat and clean and gives a no-nonsense impression.

8Layered Shag

This pretty layered shag gives off a very feminine vibe. A woman’s femininity doesn’t end when she turns 50, and this hairstyle just about emphasizes it. Lovely!

9Long Straight Bob

This long straight bob is really sweet. It is so casual and can still be easily styled into something more formal. It is a nice comfortable length too.

10Short Curls

This is a fantastic hairstyle and tells of maturity and self-confidence. It may take a while to style it, as these beautiful curls need a bit of help from hair curlers, but the results are truly worth it.

11Blonde Long Bob with Bangs

Bangs are a great way to look and feel younger in an instant. However, you should be careful to choose a style that suits your face shape and make sure it doesn’t get in the way of your glasses.

12Long Dirty Blonde

A lot of women over 50 tend to cut their hair shorter as they age. But that doesn’t have to be the case for everyone. Anyone can rock long hair – it just takes a bit of time to groom.

13Long Flowing Natural Hair

We look up to older women who let their natural locks flow free. It’s such a wonderful celebration of age, beauty, and riches – with silver in their hair and gold in their heart.

14Long Shaggy Hair

If you have naturally wavy hair, a shaggy haircut is a quite flattering option. Remember to care well for your curls such that it won’t get too unruly and end up looking ungroomed. To maintain your waves, simple towel drying and using a bit of product while your hair is damp will do the trick.

15Loose Side Braid

This is such a wonderfully carefree and youthful style, and we cannot just help but smile when we see it. A pair of silver wire-rimmed glasses will totally fit here!

16Medium Pixie with Bangs

This is a comfortable length for those who prefer not to have the traditional pixie cut. A pixie might be too harsh a contrast for someone with soft features, thus a bit of side bangs is needed to soften the look out.

17Loose Bun with Side Pieces

Being well-groomed doesn’t necessarily mean a slicked back ‘do. This loose bun with side pieces is a perfect example of being well-groomed and stylish.

18Medium Bob with Side Bangs

A simple way to update any look is to get bangs and a side part. It is very simple but very effective. Side bangs frame the face in a soft way that is flattering to everyone, and the change is not that drastic.

19Messy Bob

A messy bob is a stylish way to style a short bob. It is easy and not at all time consuming. Women 50 and over can easily rock this look!

20Messy Bun

It is a personal preference, really, whether one would go for the messy bun or a slick bun. In this instance, a messy bun looks great. It looks relaxed and casual, the perfect pair for turquoise-colored glasses and a cup of coffee.

21Messy Natural Curls

Isn’t this just beautiful? A woman embracing her natural beauty. Remember to use a cotton t-shirt when drying your hair to maintain your curls.

22Messy Lob

This is a quite flexible hairstyle which allows you to style it up or down. A nice loose bun to get you through the day, and letting it all down and relaxing with a glass of wine in the evening.


A wonderfully fun haircut for women of all ages. Show off your wild side by using a bit of product to feather out the edges and go for a punky look!


This is probably the epitome of a power woman with self-confidence through the roof. People sense you are in the building even before you walk into the room. This hairstyle is hot and well-suited to support the crown that you wear.

25Chin-length Bob

This very practical and sweet hairstyle is an awesome choice because the hair ends just below the chin, making a nice frame for the face. Your best asset is in focus.

26Pulled-back with Side Fringe

This is quite an elegant hairstyle, however simple it is, and fits beautifully with glasses too. Lightly run an iron through your fringe to tame them and get a sleeker look.

27Wavy Redhead

Be it natural or not, red is always a fun color to have. When thinking of going red, always keep in mind to choose tones that are suitable to your own skin’s undertone. Cooler undertones work well with cinnamon, copper, and crimson, while warmer tones work well with mahogany, auburn, and orange-red.

28Straight Bob with Bangs

A nice straight bob with bangs, be it chin length or longer, is very practical and very pretty. It doesn’t need a lot of time to style into place, but might be quite hard to work with if you want an updo. However, when accessorized the right way, an updo is no longer necessary. We are loving the pearls on this one!

29Straight Bob with Side Pompadour

This is a very pretty hairstyle slightly reminiscent of the good old 90s, but none of the violent hair teasing. The side pompadour is subtle, sweet and stylish. A good hairspray will hold this style in place for the rest of the day.

30Short Layered Cut

We are loving the attitude with this cool hairstyle. She is sporting a messy, layered haircut with a slight pompadour and feathered edges in the bottom. All of this is just really cool from the get-go.

31Brushed Back Short Hair

You might say that there is nothing very exciting with this look, but it’s exactly its simplicity that makes us love it. To hold your hair into place, you need just a cherry-sized drop of product and you can use your fingers to brush your hair away from your face.

32Messy Bob with Deep Side Part

This is such a comfortable look with no fuss at all. The deep side part gives the effect that you have more volume to your hair than you actually do.

33Short and Spiky Hair

What do we say to women over 50 with short and spiky hair? YES! YES! YES! As stated earlier, we strongly believe that everyone should be able wear whatever hairstyle they want regardless of age. So rock those spikes, you wild thing you.

34Undercut Pixie

This is such a fun haircut and we love that women over 50 are getting them! Stylish and punky hairstyles do not belong to just the younger ones, you know. If you want an undercut, go and get it!

35Formally Swept

Here is a more formal hairstyle which you can use for business meetings and such. Sweeping the whole of your to hair into the side, and feathering out your ends. It gives the effect of more voluminous hair and the feathered edges makes a nice frame for your face.



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