14 Chic Short Hairstyles For Women Over 50 That Look Great With Glasses

Finding the perfect short hairstyle after 50 can feel like a balancing act, especially when you wear glasses. The right cut should complement your facial features, work harmoniously with your frames, and reflect your personal style while being practical for your lifestyle.

 Short hair offers numerous advantages for women over 50, from easier maintenance to a more youthful appearance, and when paired thoughtfully with glasses, it can create a sophisticated, polished look that’s both modern and timeless.

1. Classic Bob with Side Part

The classic bob remains a timeless choice that works beautifully with glasses. This versatile cut hits just below the chin and features clean, straight lines that create a polished frame around your face.

Styling Tips: Use a round brush while blow-drying to create a slight inward curve at the ends. Apply a smoothing serum to eliminate frizz and add shine. For extra volume, use a root-lifting spray at the crown.

Best For: Oval and heart-shaped faces with straight to slightly wavy hair. The clean lines complement angular glasses frames, while the length provides balance for larger frames.

2. Textured Pixie Cut

A textured pixie cut adds youthful energy and works exceptionally well with glasses by keeping hair away from the frames. The choppy layers create movement and dimension while maintaining a low-maintenance appeal.

Styling Tips: Apply a texturizing cream to damp hair and scrunch gently. Use your fingers to tousle the layers for a natural, effortless look. A light-hold hairspray will keep the texture in place without stiffness.

Best For: Oval, heart, and diamond-shaped faces with fine to medium hair texture. Perfect for those who want minimal styling time while maintaining a chic appearance.

3. Asymmetrical Lob (Long Bob)

The asymmetrical lob features one side longer than the other, creating visual interest and modern sophistication. This cut works particularly well with glasses as it draws attention to your eyes while maintaining elegant proportions.

Styling Tips: Use a flat iron to enhance the sleek lines, or add beach waves with a curling iron for a softer look. Apply a heat protectant before styling and finish with a light oil for shine.

Best For: Round and square faces with straight to wavy hair. The asymmetry helps elongate round faces and soften angular features, while the length provides balance for statement glasses.

4. Layered Shag

The modern shag brings back the beloved 70s style with contemporary updates. Multiple layers create volume and movement, while the slightly messy texture adds a carefree, youthful vibe that pairs beautifully with glasses.

Styling Tips: Enhance natural texture with a curl-enhancing mousse on damp hair. Scrunch gently and air-dry, or use a diffuser for more defined waves. Finish with a texturizing spray for added grip.

Best For: All face shapes with wavy to curly hair. The layers add volume to fine hair while reducing bulk in thick hair. Works especially well with cat-eye or round glasses frames.

5. Sleek Graduated Bob

A graduated bob is shorter in the back and longer in the front, creating a sophisticated silhouette that perfectly frames glasses. The sleek finish adds polish and elegance to any look.

Styling Tips: Use a straightening brush or flat iron to achieve the sleek finish. Apply a smoothing cream before styling and seal with a shine spray. Regular trims every 6-8 weeks maintain the precise shape.

Best For: Heart and diamond-shaped faces with straight to slightly wavy hair. The longer front pieces soften angular features and complement both delicate and bold glasses frames.

6. Tousled Crop

The tousled crop is a short, deliberately messy style that creates a relaxed, effortless appearance. This cut works wonderfully with glasses by keeping hair off the face while maintaining a stylish, lived-in look.

Styling Tips: Apply a volumizing mousse to damp hair and rough-dry with your fingers. Use a small amount of texturizing paste to define pieces and create separation. Avoid over-styling to maintain the natural, tousled effect.

Best For: Oval and square faces with fine to medium hair. The tousled texture adds volume and movement, while the short length keeps focus on your glasses and facial features.

7. Side-Swept Bangs with Short Bob

Combining a short bob with side-swept bangs creates a flattering frame that works harmoniously with glasses. The bangs add softness and help balance the proportions of both your face and eyewear.

Styling Tips: Blow-dry bangs with a round brush, directing them to the side. Use a light-hold pomade to keep them in place without looking greasy. Style the bob with gentle curves for a soft, feminine finish.

Best For: Long and square faces with straight to wavy hair. The bangs help shorten a long face while softening angular features. Works best with thinner glasses frames to avoid overwhelming the look.

8. Choppy Layers with Volume

Choppy layers create texture and movement while adding significant volume to fine or thinning hair. This style works exceptionally well with glasses by creating a full, youthful appearance that balances eyewear proportions.

Styling Tips: Use a volumizing shampoo and conditioner, then apply a root-lifting spray before blow-drying. Use a round brush to lift hair at the roots and create volume throughout. Finish with a light-hold hairspray.

Best For: Round and oval faces with fine to medium hair. The choppy layers add fullness and movement, while the volume helps balance larger glasses frames.

9. Wispy Pixie with Longer Top

This pixie variation keeps length on top while maintaining short sides, creating a modern, edgy look that pairs beautifully with glasses. The wispy texture adds femininity and softness to the overall style.

Styling Tips: Apply a small amount of styling cream to damp hair and use your fingers to create texture. For added volume, use a blow dryer with a diffuser attachment. Finish with a texturizing spray for hold.

Best For: Oval and heart-shaped faces with fine to medium hair. The longer top creates height and balance, while the wispy texture softens angular glasses frames.

10. Curly Bob with Natural Texture

Embracing natural curls in a bob length creates a beautiful, authentic look that works wonderfully with glasses. The curls add volume and frame the face while maintaining a sophisticated appearance.

Styling Tips: Use a curl-defining cream on damp hair and scrunch gently. Air-dry or use a diffuser on low heat. Avoid brushing when dry to prevent frizz. Refresh curls with a leave-in conditioner spray.

Best For: All face shapes with naturally curly hair. The rounded shape of curls complements both angular and round glasses frames, while the volume adds youthful energy.

11. Feathered Cut

The feathered cut features layers that flip away from the face, creating a light, airy appearance that works beautifully with glasses. This style adds movement and softness while maintaining a polished look.

Styling Tips: Use a round brush while blow-drying to create the characteristic feathered effect. Apply a light mousse for hold and finish with a flexible hairspray. The key is to brush the layers away from your face.

Best For: Square and round faces with straight to wavy hair. The feathered layers soften angular features and add width to narrow faces, while the movement complements cat-eye or rectangular glasses.

12. Sleek Chin-Length Bob

A sleek chin-length bob creates a sophisticated, polished look that pairs perfectly with glasses. The clean lines and precise length create a timeless style that works in both professional and casual settings.

Styling Tips: Use a flat iron to achieve the sleek finish, working in small sections. Apply a heat protectant first and finish with a shine serum. Regular trims are essential to maintain the precise shape.

Best For: Oval and heart-shaped faces with straight to slightly wavy hair. The sleek lines complement modern glasses frames while the length provides balance for both delicate and statement eyewear.

13. Textured Shag with Fringe

A textured shag with fringe combines the best of both worlds: the movement and volume of a shag with the face-framing benefits of bangs. This style creates a youthful, modern look that works beautifully with glasses.

Styling Tips: Apply a texturizing mousse to damp hair and scrunch for natural texture. Use a blow dryer with a diffuser or air-dry for a more relaxed look. Style the fringe with a round brush for a smooth finish.

Best For: Long and rectangular faces with wavy to curly hair. The fringe helps shorten a long face while the shag layers add width and softness to angular features.

14. Stacked Bob with Volume

A stacked bob is shorter in the back and gradually gets longer toward the front, creating natural volume and a flattering silhouette. This style works exceptionally well with glasses by adding height and creating a balanced look.

Styling Tips: Use a volumizing mousse on damp hair and blow-dry with a round brush, lifting at the roots. The stacked layers naturally create volume, but you can enhance it with a root-lifting spray. Finish with a light-hold hairspray.

Best For: Round and square faces with straight to wavy hair. The stacked layers add height and elongate the face, while the volume helps balance larger glasses frames.

Your Journey to the Perfect Glasses-Friendly Cut

Choosing the right short hairstyle when you wear glasses is about finding the perfect harmony between your face shape, hair texture, lifestyle, and personal style. Remember that the best cut is one that makes you feel confident and comfortable. 

Consider consulting with a professional stylist who can assess your individual features and recommend modifications to these styles that will work best for you. 

Don’t be afraid to show your stylist photos of styles you love, along with pictures of your glasses, to help them understand your vision. With the right cut and styling techniques, you can achieve a look that’s both practical and stunning, proving that short hair and glasses make a winning combination at any age.