Finding the right hairstyle that works with glasses can be tricky, but it’s definitely worth the effort.
Medium-length hairstyles offer a versatile canvas for personal style, whether you prefer polished or laid-back vibes.
Combine these with the right glasses, and you’ll elevate your appearance with ease.
In this guide, I’ll show you 24 medium-length hairstyles for men with glasses to help you look stylish and confident in any setting.
1. Sleek Side Part with Tortoise Shell Frames
The sleek side part pairs elegantly with tortoise-shell frames, creating a polished and professional look. The glossy hair finish adds sophistication, while the neatly styled comb lines highlight attention to detail. This hairstyle is perfect for office wear or formal events, complementing the structured aesthetic of the glasses.
2. Tousled Waves with Round Black Glasses
Tousled waves bring a casual charm to this medium-length hairstyle, while round black glasses enhance the intellectual vibe. This effortless yet stylish look works for creative environments, coffee dates, or casual outings. The soft waves perfectly frame the face and pair seamlessly with the glasses’ minimalistic design.
3. Textured Fringe with Thin Metal Frames
The textured fringe adds a modern, youthful edge to this hairstyle, balancing perfectly with thin metal frames for a clean aesthetic. This urban-inspired look is ideal for those who love blending minimalism with a hint of rebellion. The matte hair finish and edgy outfit amplify the overall vibe.
4. Shoulder-Length Layers with Vintage Round Glasses
The shoulder-length layers offer a laid-back yet elegant touch, while vintage round glasses add a retro flair. This hairstyle complements outdoor settings and timeless fashion styles. The soft autumn hues enhance the natural warmth of the hair, creating a perfect harmony with the glasses.
5. Undercut with Volume and Thick Square Frames
The voluminous top combined with a sharp undercut creates a bold contrast, while thick square glasses bring a contemporary twist. This dynamic look is ideal for those who want to stand out in professional or social settings. The hairstyle’s height and structure perfectly complement the glasses’ bold design.
6. Messy Layers with Clear Frames
Messy layers give a relaxed, approachable vibe, while clear frames add a subtle yet stylish touch to the overall look. Perfect for casual days, the combination balances effortlessness with modern sophistication. The transparent glasses highlight facial features and seamlessly complement the tousled hairstyle.
7. Side-Swept Bangs with Thin Wire Frames
Side-swept bangs lend a soft, intellectual appearance, enhanced by the refined simplicity of thin wire frames. This look is ideal for academic or professional settings, blending subtle elegance with understated charm. The glasses and hairstyle together create a polished, thoughtful aesthetic.
8. Center-Parted Waves with Square Black Glasses
Center-parted waves paired with square black glasses exude a blend of vintage and modern sophistication. This hairstyle frames the face symmetrically, adding depth to the overall look. The trench coat and glasses enhance the urban-chic aesthetic, perfect for those who appreciate timeless fashion.
9. Shaggy Layers with Rounded Frames
Shaggy layers provide a carefree, rugged charm, while rounded tortoise-shell glasses bring balance to the playful texture. This cozy, laid-back style pairs perfectly with winter settings and casual outfits, making it a great choice for weekend getaways or casual gatherings.
10. Slicked-Back Look with Oversized Frames
A slicked-back look paired with oversized glasses creates an aura of authority and sophistication. The hairstyle’s glossy texture complements the sharp edges of the frames, making it a striking choice for formal events or high-profile gatherings. It’s a bold, timeless statement.
11. Layered Bob with Oval Glasses
The layered bob brings softness and volume, while slim oval glasses add an understated elegance. This natural look is perfect for serene settings and reflective moments. The hairstyle frames the face gently, highlighting the delicate design of the glasses.
12. Voluminous Quiff with Minimalist Glasses
The voluminous quiff is bold and trendy, enhanced by the clean, minimalist aesthetic of frameless glasses. This look is perfect for urban explorers and style enthusiasts. The hairstyle’s height and texture contrast beautifully with the understated simplicity of the glasses.
13. Wavy Curtain Bangs with Square Gold Frames
Wavy curtain bangs bring a relaxed and stylish touch, perfectly paired with square gold frames for a hint of sophistication. This look suits casual outings or creative settings, offering a versatile and approachable vibe. The soft waves frame the glasses elegantly, highlighting the natural texture of the hairstyle.
14. Brushed-Back Layers with Clear Round Frames
Brushed-back layers add volume and sophistication to this medium-length hairstyle, while clear round glasses maintain a minimalist yet polished appearance. This combination works seamlessly in professional environments, emphasizing confidence and a refined style. The natural volume enhances the overall structured aesthetic.
15. Messy Beach Waves with Black Aviator Frames
Messy beach waves and black aviator frames create a carefree, adventurous look that’s perfect for seaside settings. The tousled texture exudes natural charm, while the bold glasses add a stylish edge. This combination is ideal for casual summer days and vacations.
16. Straight Cut with Tapered Sides and Thick Frames
The straight cut with tapered sides delivers a clean, professional vibe, enhanced by bold thick-framed glasses. This hairstyle is a great choice for work or networking events, offering a sharp yet approachable appearance. The combination blends functionality with style effortlessly.
17. Flow Hairstyle with Thin Metal Oval Glasses
The flow hairstyle captures a natural, relaxed vibe, perfectly matched with thin oval glasses for a minimalist touch. This look is ideal for outdoor enthusiasts and nature lovers, blending seamlessly with casual attire and rugged settings. The soft movement in the hair adds a sense of freedom.
18. Half-Up Hairstyle with Square Rimless Frames
The half-up hairstyle combines casual and formal elements, perfectly complemented by sleek rimless glasses. This versatile look transitions easily from day to evening, adding a touch of sophistication to any occasion. The natural waves add texture, balancing the polished appeal of the glasses.
19. Windswept Look with Bold Round Frames
The windswept hairstyle evokes a sense of adventure and freedom, enhanced by bold round frames for a striking contrast. This look is perfect for dynamic, outdoor settings, with the natural hair movement harmonizing with the dramatic backdrop. It’s an effortlessly stylish choice.
20. Textured Crop with Geometric Glasses
The textured crop and geometric glasses create a cutting-edge, urban-inspired look. This bold combination is ideal for those who appreciate modern fashion and architecture. The hairstyle’s clean lines and dynamic texture pair seamlessly with the unique frame design, offering a contemporary vibe.
21. Side-Swept Fringe with Transparent Square Glasses
The side-swept fringe adds a relaxed elegance, perfectly complemented by transparent square glasses for a modern twist. This hairstyle is ideal for intellectual or creative settings, offering a balance of casual and polished. The soft texture of the hair frames the face and glasses seamlessly.
22. Medium Shag with Black Rectangular Glasses
The medium shag hairstyle exudes effortless cool, with layers adding depth and movement. Paired with bold black rectangular glasses, this look is perfect for urban adventurers and trendsetters. The tousled finish enhances the overall laid-back aesthetic, blending seamlessly with casual attire.
23. Brushed-Out Waves with Gold Rim Glasses
Brushed-out waves paired with gold rim glasses create an effortlessly refined look. This combination is ideal for formal occasions or high-end gatherings, blending natural hair movement with a touch of elegance. The waves provide texture, while the glasses elevate the overall sophistication.
24. Modern Quiff with Silver Oval Glasses
The modern quiff offers timeless appeal, with its structured yet voluminous design. Paired with silver oval glasses, this look is ideal for those who appreciate understated sophistication. The hairstyle’s clean lines and height work perfectly with the sleek frames, creating a balanced and polished appearance.
Conclusion
Medium-length hairstyles pair beautifully with all types of glasses, offering endless ways to customize your look. Whether you’re aiming for professional elegance or a more relaxed vibe, there’s a style here for you.
