16 Chic Short Hairstyles for Women Over 50 With Glasses

Short hairstyles for women over 50 with glasses

A short hairstyle for over 50 with glasses is a haircut that’s designed to complement the face by considering not just your features but also the frame of your glasses. Your spectacles don’t have to serve only a single purpose – you’ll be surprised how it can be your most stylish accessory!

At 50 or above, Hollywood legends Kate Capshaw, Emma Thompson, Meryl Streep, and Diane Keaton did show the world that age is just a  number with their great haircuts and matching frames! It’s seriously amazing how much your specs can add life and fun to your look just as much as a charming cropped haircut can!

Precision cutting specialist Joan Osterberg is a pro in improving her clients’ hairstyles by working with both face shape and glasses. Plus, she demonstrates how you could use texture to your advantage in creating a fitting, put-together look.

Give thought to your desired locks’ color and length and see if they match your lifestyle, as this will determine how much upkeep you need to do. Ask your hairdresser about the deets of maintenance, depending on your chosen cut.

To all mature ladies out there, don’t let the fashionista inside of you fade with time! Choose the perfect hair for you from these trendiest short hairstyles for over 50 with glasses that you’ll find right below!

For Fine Hair

short hairstyle for over 50 fine hair with glasses
Instagram @apriltoccohair

Ideal for fine hair, this lovely short cut results to a dazzling hairstyle when colored with subtle and dimensional copper. Look creator April Tocco used Shu Uemura’s Color Luster shades reviving balm conditioner. According to her, it keeps the blonde color from fading, refreshes blonde highlights, deeply nourishes and adds vibrancy to hair. There is no chemical reaction or modification of permanent color.

For A Round Face

short hairstyle for over 50 with glasses and round face
Instagram @hausoflazaroff

For a round face woman over 50 and wearing glasses, this is the haircut you might want to get next. This cute and soft pixie cut creates texture that complements the round shape of your face. No need to overthink of beautiful hair color because a natural grey hair will do.

With Thick Hair

short hairstyle for over 50 with thick hair and glasses
Instagram @hairplvg

Having thick hair is a blessing since you can mix and match with layers and textures, like this one. The bangs add a subtle curtain effect to the eyeglasses, sealing the whole look together.

Short Layered Hairstyle

short layered hairstyle for over 50 with glasses
Instagram @_beautybybellamae

Long strands cut into layers has increased puffiness, and therefore volume. The side part is the perfect way to highlight your facial features, with your glasses and eyes even more accentuated.

For Thin Hair

short hairstyle for thin hair over 50 with glasses
Instagram @thenathanaltman

This layered crop style doesn’t take away attention to your other facial features. Its simplicity is what makes it perfect, even for thin-haired ladies. Texture and layers are what your look needs, and this style has it.

With White Hair

short hairstyle white hair over 50 with glasses
Instagram @cavabienspa

Flex those aging locks with a chic short bob with tapered ends. White hair can now be your asset as you make those frosty tips work for your modern style.

Youthful Hairstyle

youthful short hairstyle for over 50 with glasses
Instagram @salonghalda.fo

Ever imagined wearing this nouveau cut at your age? Yes, you can still flaunt this youthful style that is simply a bob with some layers and an undercut in it!

The Messy Bob

short messy bob hairstyle for over 50 with glasses
Instagram @thecreativehairdresser

This golden style is gorgeous due to its ability to show off how fluffy and full your hair still is. Great for thinning hair as well; a rugged style complements your framed glasses as much as the next look.

Very Short Hairstyle

Short hairstyles like this are convenient for the modern lady. Ladies in their fifties should not be worrying about stray hair on their eye area, so this is the perfect style for them indeed.

Q&A with style creator, Sarah Mitchell
Senior Stylist @ Lebel and Crowe Salon in Brockton Village, TO

How would you describe this look?

This look is a modern pixie cut with lots of texture. My favorite thing about this look is its versatility. One could wear it fun and textured or quite classic and pretty.

A lot of people think that short hair can only be worn one way, but the beauty of this cut is that it can be worn in two very different styles. Playful and edgy (like in the picture) or in a more classic style – think of Audrey Hepburn or Mia Farrow as reference.

The key is to have lots of softness around the face. You could achieve this by incorporating a piece-y, textured fringe and length around the ears. This keeps the haircut from looking too masculine.

Any advice for someone considering it?

The first thing that I would do is to analyze your face shape. Do you like your cheekbones and jawline? I say this because, once the hair is cut, they will be exposed. Many women love this look because they can wear a great pair of earrings and/or glasses and they become a focal point.

The day-to-day styling is great because you have to do very little! I would recommend investing in a good texture cream or hair paste. I like Kevin Murphy’s “Freehold” styling cream or the R & Co’s “Control” flexible paste. Rub a dab in your hands and apply it to the crown area of your head. You can wear it messy and playful or apply less and wear it more classic. When you have hardly any left in your hands, go through and piece out your fringe area, showing off the texture of the cut. If you have very thick hair, you will need to ask your stylist to remove extra weight and add more texture.

Short hair requires you to visit the salon more often to have your hair cut and shaped. This may be something to keep in mind. Most long haircuts can go 3 months between salon visits, but short hair is every 6 weeks or so. But who doesn’t love getting their haircut?

Short Pixie Hair

short pixie hairstyle for over 50 with glasses
Instagram @samazinghair

Q&A with style creator, Sami Copley
Hair Stylist @ Salon Zuberenz! in Lynnwood, WA


How would you describe this look?

This is a very short versatile pixie customized for her strong growth patterns. It can have a soft or strong look. I love that it shows she is strong and sassy with a flair for color!

Any advice for someone considering it?

This cut is perfect for any woman who wants a fun style without fuss in the morning. It does require a visit to your stylist every five weeks to keep it looking smart and fresh.

Short Bob Hairstyle

Q&A with style creator, Wayne French
Barber / Stylist @ Bohemia Salon in Mount Pleasant, SC


How would you describe this look?

This look is a fun, deconstructed stacked bob. It is cut with diagonal forward lines at the perimeter with chunky, razor-cut layers that are versatile enough to either angle forward to frame the face or flip out and partially back as the model demonstrates. This haircut is great for fine, straight hair as pictured but also is really fun for natural curls for a completely different look.

Any advice for someone considering it?

I love to give my customers lots of styling options to fit with our casual coastal lifestyle. Styling can be done with a blow dryer and round brush or flat iron, depending on the client’s preferences. A matte paste was used to accent the movement of the layers without the hard hold of hairspray, but some clients may prefer a stronger hold. I really enjoy the flexibility of this style.

Chin Length Hair

short chin length hairstyle for over 50 with glasses
Instagram @nwhair

Q&A with style creator, Noel Smith
Hair Artist @ Magnolia 3 Salon in Davis, CA


How would you describe this look?

This is a slightly angled bob with blunt bangs. My client loves to change her hair up often and keep her haircuts more modern and clean since she has finer hair.

Any advice for someone considering it?

I would definitely think about your at-home haircare routine and regime! My client comes in every eight weeks to touch up her color when she was red. Remember to use color-safe professional shampoo and conditioner to prolong your color.

Since you spend your hard-earned money on your hair color, maintaining at home will ensure your color last longer! When using hot tools, turn the temp down, so you don’t strip out the color or alter it. High heat can fade color quicker! For my clients who do creative color, I always recommend a color depositing shampoo and/or conditioner for your current color to maintain the tone and intensity.

Asymmetrical Bob

Q&A with style creator, Farrah Shapiro
Hair Stylist @ Valentino’s Grande Salon in Whitby, ON


How would you describe this look?

This is an asymmetrical graduated bob with a fringe and some personalizing. It’s a “modern meets classic” look. My favorite thing about this creative hair cut is how playful yet chic it is.

Any advice for someone considering it?

Maybe you’ve been getting the same classic bob haircut for years and desire a change, but not a drastic one or you desire a big change and have been thinking about it for months. This hair cut is very suitable in the workplace, and many professionals ask for asymmetrical bobs.

To maintain this creative cut, it is recommended to rebook every four to six weeks. Suitable face shapes are oval, heart, and long faces. Although, you can still rock this cut with a few minor tweaks if you do not fall into the face shape categories above.

For a smooth, touchable, and stronghold, I recommend using three products. Apply Goldwell Ultra Volume Glamour Whip 3 and Goldwell Just Smooth Thermal Spray 0 on damp hair and finish off with number Lamaur Vita/E Hairspray.

For blow-dry tips, start with setting your fringe if you have a stubborn fringe that likes to split, blow-dry side to side with a comb. Then, go in with a round brush for extra volume. Use a Denman brush for the graduation in the back and dry side to side using the round of the head to achieve a blowout look. Lastly, use a round brush for the sides and top.

Chic Super Short

chic super short hairstyle for over 50 with glasses
Instagram @salonvanitypa

Q&A with style creator, Edmondo Blando
Owner / Hairstylist @ Salon Vanity in Philadelphia, PA


How would you describe this look?

What I love about this is that it really fits her face shape and allows a lot of room for creative changes when needed, all while she can feel like she is expressed! I love that short, like this, can also be helpful for women with thick texture or even if they are fine-haired. I love that any age can do this, and coincidentally as women age, they look more youthful with pixies or shorter vs. trying to have a style that pulls down their features! I also love that it’s a wash-and-go and can fit any occasion and outfit!

Any advice for someone considering it?

The fact that every woman says, “I wish I could do that” when, in fact, they could if they would consult with an experienced hairstylist when considering this.

The upkeep day-to-day is super simple, and the cut and color are also good for 4-6 weeks. One cool thing I like is that this is a great step to take before going all gray as you can play with the right fashion tone that will lead to your silver/grey. It also looks great with some cool eyeglasses as an extra accessory!

Curly Hairstyle

Q&A with style creator, Lauren Finley
Hair Stylist @ Kenneth Brown Salons in Newport Beach, CA


How would you describe this look?

One of my favorite textures to work with is curly hair. I think that more people should embrace their natural curl instead of fighting it. I love this look on my client because all she has to do is put some product in and go. Layering and personalizing curly hair is super important for it to lay right. Any heaviness can make the shape collapse in certain areas.

Any advice for someone considering it?

This is a perfect look for anyone who does not want a lot of styling maintenance. I feel as if it can look good at any age. The key is the right product to enhance the curl, take away the frizz, and to keep the volume.

With Grey Hair

With Grey Hair
Instagram @zoesparkshair

Q&A with style creator, Zoe Sparks
Hair Stylist @ Kiss and Makeup Salon in Spokane, WA


How would you describe this look?

This cut is a short textured A-line bob. I love the versatility of this haircut because it looks great if it is styled curly and messy or smooth and sleek. It’s also so fun and sassy, and it’s an easy way to modify a short haircut into something new!

Any advice for someone considering it?

This haircut is relatively short in the back, so it does require a touch-up haircut every 4-6 weeks if you want to maintain the shape! As far as styling, it depends on your natural hair texture, but it can be straightforward to style depending on what hair product you use.

I would recommend a curl cream if you have some natural curl in your hair. If you wanted to wear it smooth, a leave-in heat protectant and a flat iron would do correctly!