13 Most Flattering Hairstyles for Women Over 50 With Glasses

hairstyles for over 50 with glasses

If you’re looking for youthful and flattering hairstyles for women over 50 with glasses, then you’ve come to the right place! Eyeglasses shouldn’t just be a necessity for prime ladies but a stylish fashion accessory as well!

First things first – check your face shape!  All aspects of your hairstyle should depend on it – from the bangs and parting style to the length – the primary goal is to find the perfect match for your face and lifestyle.

Another tip to appear younger with spectacles is to pair your haircut with a fitting color, of course, considering your specs! Take inspiration from how Helen Mirren, Meryl Streep, Salma Hayek, and Viola Davis sprightly strut on the red carpet with their matching hairstyles and glasses!

You’ll confidently believe that age is truly just a number and won’t ever limit your styling options! No matter how long your desired hair is – short, medium-length, super long – there’s undoubtedly a perfect way to look lovely with your eyewear.

Show everyone how full of life you are with an adorable hairstyle! Choose from these super trendy hairstyles for women over 50 with glasses!

Long Bob for Round Faces

Long Bob for Round Faces
Instagram @thecreativehairdresser

The long bob for round faces is ideal for businesswomen 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

Flattering Cut for a Square Face
Instagram @shelseastylist

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

Medium Length Shag

Medium Length Shag
Instagram @shesahaircutter

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.

Feathered Bob with Bangs

Feathered Bob with Bangs
Instagram @maria_colors4u

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

Shorter Cut for Fine Hair

Shorter Cut for Fine Hair
Instagram @kew_hair_design

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.

Short Curly Hair

Short Curly Hair
Instagram @_ceebeauty_

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!

Layered Haircut for Thin Hair

Layered Haircut for Thin Hair
Instagram @vamphairstudio

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 thin hair.

Textured Cut for Thick Hair

Textured Cut for Thick Hair
Instagram @lisaschwabstudio

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.

Pixie Crop with Bangs

Pixie Crop with Bangs
Instagram @the.hair.geek

The real thrill comes from working your short chop! The soft side fringe falls on your face, which makes your eyes stand out, much like your glasses!

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.

Short Bob with Side Part

Short Bob with Side Part
Instagram @chroma.carmona

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


How would you describe this look?

Every woman at every age deserves to feel beautiful and sexy, and that’s what this haircut does for her face shape.

Any advice for someone considering it?

This haircut is designed to give every face shape 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

Very Short Spiky Pixie
Instagram @petekhair

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 haircut is how the texture is such a strong contrast to her glasses. 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 to be maintained every 5-6 weeks. My client also uses purple shampoo to keep her silver hair bright!

Short Grey Pixie Cut

Short Grey Pixie Cut
Instagram @bilo_doing

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 for my older client. 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! It looks great with her glasses.

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 who want to look trendy no matter their age.

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?

This look 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, 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. 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!