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13 Most Flattering Hairstyles for Women Over 50 With Glasses

Short Grey Pixie Cut


Q&A with style creator, Chantelle Bilodeau
Senior Hairstylist & Creative Director @ Sin 7 Salon in White Rock, BC

How would you describe this look?

This look is an updated version of a timeless bowl cut made a little softer. The trend right now for bowl cuts is the shaved sides, but I wanted my guest to have a bit of softness around her edges. My favorite part is her super short and heavy fringe! This looks great for women with glasses and fun frames.

Any advice for someone considering it?

Make sure you learn all the ways you can style it. It’s pretty texturized, so you can get away with minimal styling tools and products. If you want to play with the style, you should learn all the options!

It’s a quick style for active women over 50 who want to look trendy no matter their age.

Medium Length Shag


This is one of the best medium length hairstyles for women over 50 with glasses and clear frames! This is a look from the ’70s can very well make you look younger than over 50! The bangs and waves on this shoulder-length cut all point towards your eyes, which can very much highlight its beauty.

Short Curly Hair


This short curly hair for a woman over 50 is beautiful. The curls would seem like the accessory your textured bob needs! Just like how your eyewear can be your fashion piece, wear your ginger curls elegant and proud!

Pixie Crop with Bangs

Pixie hairstyles for women over 50 with glasses look super cute! The real thrill comes from working your short chop! The soft side fringe falls on your face, which makes any 50-year-old woman’s eyes stand out, much like your glasses and their frames!

Q&A with style creator, Dara Casterline
Hair Stylist @ Capretti & Co in Pittsburgh, PA

How would you describe this look?

I love pixies. I feel that they are classic yet fun. My favorite thing about this haircut is that it can be customized to each person, and it is fast and easy to style.

Any advice for someone considering it?

This look is perfect for fine hair that tends to lack volume. I typically recommend a mousse applied at the root on towel-dried hair, and after the hair has been dried, I recommend applying a light texturizing product or spray. I use Aveda Phomollient and Air Control hair spray.

This cut is perfect for anyone who doesn’t have a lot of time to get ready in the morning but does require more frequent visits to the salon to maintain.

👉 Check out these easy to style wash and wear hairdos for ladies in their fifties

Long Bob for Round Faces


The long bob for round faces is ideal for businesswomen in their 50s and laid back ladies alike. This cut, partnered with the everyday bangs, can turn your rounded sides to a more edged and elongated appearance.

Flattering Cut for a Square Face


Having longer locks on the front, along with full bangs, cut the rigid appearance of a square-shaped face for women aged 50. The gold frames on these glasses may have a rounder frame so that the face has more curved patterns.

Feathered Bob with Bangs


Comb out your pixie using a wide-toothed comb for this feathered look. The bangs on a 50-year-old woman may hang loose over the forehead or may slightly touch your eyewear for that weightless look.

Shorter Cut for Fine Hair


More layers on cropped hair beget incredible waves and textures, just like this pixie cut! A messier short style along with your trendy glasses, maybe your perfect ingredients for a younger look for 50+ women.

Layered Haircut for Thin Hair


When it comes to hairstyles for women over 50 with glasses and thin hair, it’s all about texture. Grab a bunch of locks and trim them successively, following a downward pattern. These produce shorter strands that are awesome for a fuller body perfect for women in their 50s with thin hair who have glasses and thin frames.

Textured Cut for Thick Hair


What a stylish textured cut for ladies over 50 with glasses and thick hair. After shearing in short lengths, blow-dry while brushing to keep the form. You can add bangs and some fringes to frame the face for a more youthful look.

Short Bob with Side Part


Q&A with style creator, Lana Carmona
Hair Stylist / Colorist @ Hair Loft Salon & Spa in Salina, KS

How would you describe this look?

All 50-year-old women deserve to feel beautiful and sexy, and that’s what this haircut does for her face shape and frames.

Any advice for someone considering it?

This haircut is designed to give every face shape the confidence because when you look good, you feel good! It’s easy to style with only 4 curls, and you can wear it for days with Redken’s powder grip and dry shampoo.

Very Short Spiky Pixie


Q&A with style creator, Pete Koziell
Barber @ Analog Hair in South Yarra, MEL

How would you describe this look?

This is a heavily texturized crop haircut.

My client had shaved her hair for charity, cutting out all of her old brunette permanent color. When her hair grew back, both she and I loved her natural silver color. She had such thick hair that I couldn’t texturize it enough, which made for a great effect.

My favorite thing about this 50-year-old woman haircut is how the texture is such a strong contrast to her glasses and purple frames. It brings attention to both!

Any advice for someone considering it?

This is a great modern haircut to suit women who don’t want to be held back by their hair. The heavy texture requires minimum styling. However, I would recommend this hairstyle with frames to be maintained every 5-6 weeks. My client also uses purple shampoo to keep her silver hair bright!

Shoulder Length Angled Bob


Q&A with style creator, Shania Tan
Hairstylist @ Hair etc. by Shania in Chicago, IL

How would you describe this look?

Just like her glasses and frames, this hairstyle is bold. According to Jo-Ellan Dimitrius, “A woman with short hair is perceived as confident – not having to hide anything.”

Women are always expected to have long hair and show their femininity, and in contemporary American culture, women with short hair are more often seen as less feminine but more professional. In truth, it radiates boldness – breaking the perception of women in society.

My name for it is an ashy angled bob. I texturized her ends for some movement to her hair.

Any advice for someone considering it?

To pull off this haircut for women over 50 with glasses, you should be bold enough to chop inches off. You should be willing enough to have this haircut in the long run because growing your hair out is not a piece of cake.

Also, consider your face shape. There are different types of short haircuts these days, and you just have to figure out which one fits your face shape and if you’re wearing glasses and frames. People with oval-shaped faces can pull off any haircut.

Lastly, you should be able to maintain your hair. Having less amount of hair does not mean less amount of maintenance. I, myself, do have short hair, and it is hard to manage it. I have to invest time to make it look good.

As long as you’re willing to consider the things I just mentioned, then you are good to go!