Short Hairstyles for Women Over 50 with Glasses

Chic, Sophisticated & Effortlessly Flattering Looks

Glasses can be the ultimate accessory, but pairing them with the perfect short hairstyle? That’s a power move. Whether you’re going for a classic vibe or something a little edgy, the right haircut can enhance your natural beauty, flatter your frames, and turn heads in the best way possible.

For women over 50, short hairstyles offer easy maintenance without sacrificing style. Combine that with the right pair of glasses, and you’ve got a timeless, confidence-boosting look.

Below, we’ve rounded up 5 short hairstyles for women over 50 with glasses that are elegant, modern, and incredibly flattering.

Table of Contents

1. Layered Pixie with Side-Swept Bangs

Want volume, shape, and movement? This is your go-to. The layered pixie adds fullness around the crown while side-swept bangs draw attention to your eyes—perfect for showing off stylish glasses. This cut works wonders on fine or thinning hair and frames the face beautifully.

Best for: Oval, square, or heart-shaped faces
Styling tip: Use a volumizing mousse and finger-tousle for a natural finish.

2. Soft Feathered Bob

If you prefer something soft yet structured, a feathered bob is a flattering option. Layers soften your facial features and the glasses, creating a balanced and gentle look. This cut adds elegance without trying too hard—ideal for both everyday and special occasions.

Best for: Round or oval faces
Styling tip: Use a round brush while blow-drying for that bouncy, feathered effect.

3. Choppy Textured Crop

Ready to show a little personality? The choppy textured crop is playful and youthful. It’s bold without being too extreme and adds definition to your cheekbones and jawline. Glasses with bold frames look extra fabulous paired with this edgy cut.

Best for: Heart-shaped or angular faces
Styling tip: Use a texturizing paste to bring out the choppy layers.

4. Classic Tapered Cut

Sleek, chic, and oh-so-elegant, the classic tapered cut is for women who love minimalism with style. It hugs the head in all the right places and looks especially good with structured or retro-style glasses. Bonus: it’s super low-maintenance.

Best for: Oval, square, or long faces
Styling tip: Keep the sides neat and smooth with a lightweight pomade.

5. Curly Short Shag

Curly hair and glasses? Yes, please. The short shag is perfect for embracing your natural texture while adding shape. Layers help curls fall beautifully around the face, and the look pairs perfectly with soft or oversized frames.