As an expert in hairstyling, I understand that finding the right hairstyle can be a game-changer for men over 50 who wear glasses. It’s not just about style; it’s about expressing yourself and feeling confident.
How can you find a hairstyle that complements both your age and your eyewear? The answer often lies in balancing personal style with practicality.
I’ve seen firsthand how the right haircut can highlight facial features and even change someone’s outlook. Glasses add a unique element to your look, making it even more crucial to choose a haircut that flatters your face shape and aligns with your lifestyle.
1) Silver Fox Side Part

I love suggesting the Silver Fox Side Part for men over 50 with glasses. This look is stylish and neat, making it perfect for gentlemen who want to embrace their gray hair with confidence.
The side part creates a clean line that adds structure to your style. It’s especially great for highlighting silver hues, which can convey wisdom and experience. You can easily achieve this look with a good comb and some styling product to hold the part in place.
2) Classic Caesar Cut

The classic Caesar cut is a short, neat hairstyle that pairs well with glasses. I enjoy its timeless appeal, inspired by Roman history. It features a straight fringe that falls forward, framing the forehead nicely.
This style adds a touch of sophistication. It’s easy to maintain, making it a favorite among older men. It’s ideal for those looking for a stylish, low-maintenance option that complements eyewear effortlessly. The clean lines of the Caesar cut offer a polished look that’s both modern and classic.
3) Textured Crop

I love a textured crop for men over 50 with glasses. It’s both practical and stylish. The textured look adds volume and interest, making hair appear fuller, which is great for anyone dealing with thinning hair.
It’s easy to manage, too. You can keep it neat or add some styling product for a more laid-back vibe. This flexibility makes it a top pick for older men who still want a youthful flair.
4) Wavy Pompadour

When working with a wavy pompadour for older men with glasses, I focus on a style that blends sophistication and flair. This look keeps longer waves on top for a relaxed vibe that complements glasses well.
To achieve this style, using a quality pomade enhances the natural waves. This provides both structure and a light hold.
A wavy pompadour with an undercut adds depth, ensuring the pompadour is the star. It’s a look that brings out confidence, perfect for anyone looking to make a statement.
5) Elegant Comb-Over

I like recommending the elegant comb-over to men over 50 who wear glasses. It’s a classic style that works well with various hair types and lengths. This hairstyle is perfect for adding a bit of sophistication and charm.
To achieve this look, you can keep the sides shorter while letting the top stay long enough to sweep over. Pairing the comb-over with smart glasses can bring a refined touch to your overall appearance. It’s practical and stylish, making it a popular choice among mature gentlemen.
6) Modern Quiff

The modern quiff is a timeless style that adds a touch of sophistication and flair. I find this hairstyle works great for men over 50 who wear glasses, as it balances the face nicely. The quiff involves longer hair on top that you can style back with volume.
You can pair the quiff with a stylish taper on the sides for a clean look. It suits both thin and thick hair, making it versatile. For inspiration, check out these quiff hairstyle ideas.
7) Undercut with Beard

An undercut with a beard can add a fresh twist for the mature male. Short on the sides and fuller on top, the style pairs well with glasses for a distinguished look. Adding a beard can make the combination more stylish by framing the face nicely.
Shaping the beard based on facial features is important. If you’re going for something trendy, consider a ponytail undercut with a goatee for a unique look. This style suits both casual and formal settings, making it versatile and modern.
8) Disconnected Undercut

The disconnected undercut is a bold choice for men over 50 who wear glasses. This hairstyle emphasizes a sharp contrast between longer hair on top and shorter sides. It offers an edgy yet sophisticated look.
I love how this style accommodates all hair types. You can keep the top slicked back or add some texture for a casual vibe. Pairing it with glasses adds a modern twist to your style.
Whether you prefer a neat or messy finish, this cut ensures you stand out, boosting confidence with its unique flair.
9) Low Fade with Glasses

I love how a low fade can really complement glasses on men over 50. This haircut gradually shortens the hair from the temples to the ears, creating a clean look. It gives your overall appearance a modern touch.
The low fade is versatile and can pair well with different hairstyles. Whether sporting short textures or longer hair on top, it works. This style emphasizes the features of your face, making your glasses stand out in a stylish way.
10) Brush-Up Hairstyle

The brush-up hairstyle is a great choice for men over 50 with glasses. I find it both stylish and easy to maintain. This look adds height and volume, making it ideal for thinning hair.
To achieve this style, I recommend using a light styling gel or mousse. Brush the hair upward, working from the front to the crown. It pairs well with most glasses styles, adding a youthful touch to your overall appearance.
11) Sleek Back Undercut

I love the sleek back undercut for men over 50 with glasses because it’s both stylish and easy to manage. This look works well with glasses, offering a clean and sophisticated appearance. For this style, short sides blend seamlessly with longer hair on top.
Achieving the sleek look requires at least three inches of hair to work with. I suggest using a good pomade or gel to keep the hair smooth and in place. This haircut can highlight facial features, and it’s a favorite among those looking for a modern update.
12) Curly Top Fade

I enjoy styling the Curly Top Fade for men over 50 who wear glasses. It’s stylish yet easy to manage. This look keeps the sides short with a fade, while the top stays full and curly. It’s a great way to showcase natural curls and adds a youthful vibe.
With the right styling products, curls stay defined without looking messy. It’s also a versatile style that can suit different face shapes and types of glasses. For more inspiration, check out these curly haircuts for older men.
13) Stylish Crew Cut

I love how versatile the crew cut can be, especially for men over 50 with glasses. It’s neat and manageable yet offers multiple styling options. Keeping the sides short and the top slightly longer can create a refined look that highlights facial features.
This hairstyle pairs well with different frame styles, from classic to modern. It’s low-maintenance but can easily be spruced up with some hair product for a polished appearance. Whether you’re going for a professional look or a casual vibe, the crew cut adapts beautifully to suit your needs.
14) Salt and Pepper Waves

I always find that salt and pepper waves offer a classic and stylish look for men over 50. This hairstyle showcases natural hair color while adding a touch of sophistication.
To achieve these waves, let your hair grow to a medium length. Use a light styling cream to enhance the natural wave pattern. Keep the sides short for contrast, which complements the glasses perfectly. This look works well with a beard or clean-shaven face, adding depth and character.
15) Short and Spiky

I love the short and spiky look for men over 50, especially with glasses. It’s youthful and full of energy without trying too hard. This style works great if you prefer low upkeep but want a bit of edge.
I recommend using a light styling gel or pomade to give the spikes some texture. It’s ideal for those with thinner hair, as it gives a fuller appearance. This cut pairs well with a well-kept beard to complete the look.
16) Layered Cut with Fringe

The layered cut with fringe can really transform a look for older men with glasses. This hairstyle adds texture and volume, making it perfect for those wanting to keep a youthful appearance. The fringe can soften facial features and draw attention to the eyes.
The layers add depth, giving thinning hair a fuller look. It’s easy to maintain with regular trims and minimal styling, making it ideal for those who prefer a low-maintenance routine. This style pairs beautifully with various glasses, complementing both casual and formal settings.
17) Gentleman’s Slick Back

I really do like the Gentleman’s Slick Back for men over 50 with glasses. This style is sleek and sophisticated, perfect for any setting. With longer hair on top and neatly combed back, it pairs beautifully with the right frames.
The key is keeping the sides short and tidy. A pomade or gel helps maintain the smooth, polished look throughout the day, while adding a touch of shine. It’s a classic choice that emphasizes confidence and charm.
18) Casual Messy Hair

Casual messy hair is a laid-back style that’s perfect for those who want a relaxed look. I often recommend this style because it requires minimal effort and works well with different hair types. Just a bit of styling cream or mousse is enough.
Letting the hair fall naturally can highlight glasses, creating a balanced appearance. This style also adapts easily to both formal and informal settings.
19) Buzz Cut with Frames

Wow! What’s not to like about the buzz cut for men over 50 who wear glasses? It’s a low-maintenance look that works great with any frame style. The clean, short hair really highlights your glasses and can add a modern touch to your appearance.
Frames can make a big style statement, and a buzz cut provides the perfect backdrop. Whether your glasses are bold or understated, this combo gives you a sophisticated and fresh look. The simplicity of the buzz cut lets your frames stand out, making it an excellent choice for anyone wanting an effortlessly stylish appearance.
20) Distinguished Ivy League

When styling a distinguished Ivy League haircut, I always recommend starting with at least an inch and a half of hair length. This classic cut, also known as the Harvard or Princeton cut, balances a short length with a side part. It’s ideal for those who wear glasses, providing a clean and polished appearance.
I find that using scissors, not clippers, gives the most refined look. This approach ensures the hair on top remains slightly longer, offering versatility. Whether your hair is wavy or straight, the Ivy League cut complements your facial features and eyewear seamlessly.
21) Sophisticated Faux Hawk

I love the sophisticated faux hawk for men over 50 with glasses. The faux hawk offers an edgy yet polished look. It adds height to your hair without being too wild.
Styling is simple. First, apply a little hair wax or pomade. Next, use a comb to bring the sides towards the center. Finally, use a blow dryer to give it volume. This style works well with both prescription and reading glasses, making it versatile and modern.
22) Professional Short Pompadour

The professional short pompadour can give a refined look while being easy to maintain. This style features short sides that keep things neat and a voluminous top that offers a bit of flair.
To achieve this look, I recommend using a good volumizing product and a hairdryer to create lift. It’s a great choice for highlighting facial features without overwhelming your style. Keep it sharp and clean for an effortlessly sophisticated appearance.
23) Retro Side Swept

I love the Retro Side Swept look for men over 50 with glasses. It combines a classic vibe with a touch of modern style. This hairstyle works well with medium-length hair, where the hair is gently swept to one side. The side sweep adds a bit of elegance and sophistication.
Glasses can further enhance this look. If you wear vintage-style frames, it can create a charming and cohesive appearance. It’s a versatile style that suits many face shapes and can be easily maintained with regular trims to keep everything neat.
24) Medium Length Layers

Medium-length layers offer both volume and texture to hair. This style suits men over 50 who wear glasses perfectly because it frames the face without overpowering it. The layers add dimension and can easily be styled to look casual or more polished.
Keeping hair at a medium length with layers gives flexibility. You can add a bit of product for volume or leave it natural for a relaxed feel. For men with thick hair, this style brings balance, allowing glasses to complement the look without being overshadowed.
25) Neat and Tidy Caesar

I do like the Neat and Tidy Caesar for the more mature male, especially those wearing glasses. This classic haircut features short, well-trimmed sides and back, with a bit of length on top to create a neat fringe. It’s a low-maintenance style that pairs perfectly with glasses, giving a smart and sophisticated look.
To style, I recommend using a matte hair product to keep the top in place without looking too shiny. The Neat and Tidy Caesar is great for those who want a clean and timeless look.
Understanding Hairstyles for Men Over 50
When choosing a hairstyle, face shape, hair texture, and density all matter. Picking a style that suits your face can enhance your features, while the right cut accommodates your hair’s texture and fullness, creating a flattering look.
Choosing the Right Hairstyle for Your Face Shape
Choosing the best hairstyle for your face shape can make a noticeable difference. For example, a square face benefits from haircuts like the classic side part. It helps soften the angles.
On the other hand, those with round faces might prefer styles that add some height. Styles with more volume on top and shorter sides, like a crew cut, can help create a balanced look. Understanding these nuances will help you find a style that makes you feel confident.
Importance of Hair Texture and Density
Hair texture and density play a big role in how a hairstyle looks and feels. Thicker hair offers more styling options, allowing for choices like layered cuts or longer styles.
Meanwhile, finer hair may benefit from shorter styles to add volume and fullness. It’s important to account for how much time you’re willing to spend styling.
Opting for manageable options like a tapered crop top could fit into a busy schedule well. Recognizing these aspects can lead to a hairstyle that feels both comfortable and stylish.
Styling Tips for Men Over 50 with Glasses
Finding a hairstyle that works well with glasses can make a big difference in how you look and feel. There are some helpful tips for complementing your hairstyle and maintaining a modern appearance. Let’s explore them.
Complementing Your Hairstyle with Different Types of Glasses
I always emphasize matching your glasses to your hairstyle. If you wear oversized rectangular glasses, a neat and tidy cut like a crew cut can create a balanced look.
For those who prefer more rounded frames, consider styles that create vertical lines. A side part can add sophistication and elongate the face, making it a good choice.
Experiment with contrast. Pair sleek, modern frames with textured hairstyles for a stylish appearance. Different glasses can dramatically change how a hairstyle looks, so don’t hesitate to try a few options.
Maintaining a Modern Look
Staying modern with age is about making small changes to your hairstyle. I suggest trying a classic taper fade. It never goes out of style and pairs well with glasses, offering a clean look. Regular trims help your hairstyle stay fresh and sleek. Keep your hair moisturized to avoid a dry or frizzy appearance, which can age you quickly.
Trying colors is another way to stay contemporary. Subtle highlights can add depth to your hair and hide grays. Good products are the secret. Use lightweight styling products to maintain volume without weighing hair down. Stick to simple products to avoid a greasy look.
Common Challenges and Solutions
I’m here to help tackle some common hair challenges older men might face. Whether dealing with thinning hair or managing greys, there are easy solutions to keep your style sharp and flattering.
Thinning Hair Solutions
Thinning hair can be a big concern as we age. One effective trick is to go for a cut with some layers. This can add volume and depth, making your hair look fuller. A tapered crop top is also a great option. It keeps hair short but stylish, with added texture on top.
I often suggest using volumizing shampoos or products. These can add lift at the roots and create an appearance of thicker hair. You might also consider a hairstyle that’s shorter on the sides to highlight the thicker areas on top.
Managing Grey Hair
Grey hair is natural and can look quite distinguished. Keeping your hair healthy is key. Moisturizing shampoos and conditioners can help maintain shine and softness, which is essential when hair turns grey.
A side-parted style can be a classy choice. It adds structure and suits the more mature hair texture.
For those wanting to maintain their natural color mix, try a gradual hair color treatment that subtly blends greys without being too noticeable. This way, you keep a natural look while enhancing your hair’s overall appearance.