There’s something inherently captivating about the Old Money aesthetic—effortless sophistication, understated luxury, and a sense of timeless refinement.
For men, this style isn’t just about wearing tailored suits or owning leather-bound books; it extends to their grooming choices, particularly their hairstyles. Old Money hairstyles are clean, polished, and exude confidence without trying too hard.
If you’re looking to channel that classic charm, here’s a curated list of 20 iconic Old Money hairstyles for men, complete with tips on achieving and maintaining them.
The Side Part
A quintessential Old Money hairstyle, the side part involves combing your hair to one side with a defined parting line. It’s sleek, structured, and universally flattering.
Why It Embodies Old Money Sophistication: This look has been a staple among aristocrats and businessmen for decades. Its precision mirrors the meticulousness of traditional etiquette.
How to Achieve & Maintain: Use a fine-toothed comb to create a sharp part. Apply a pomade or gel for hold and shine. Blow-dry while combing for extra polish.
Recommended Products: Suavecito Pomade, Uppercut Deluxe Pomade
The Slicked-Back Undercut
Combining modern edge with vintage flair, this style features shaved sides and slicked-back longer hair on top.
Why It Embodies Old Money Sophistication: While edgier than most Old Money styles, its clean lines and glossy finish make it an elevated choice.
How to Achieve & Maintain: Keep the sides trimmed short and use a strong-hold pomade to slick back the top. Regular trims are essential.
Recommended Products: Layrite Deluxe Original Pomade, American Crew Pomade
The Ivy League
Similar to a crew cut but slightly longer, the Ivy League offers versatility with graduated layers at the front.
Why It Embodies Old Money Sophistication: Named after prestigious universities, this haircut screams intellectual elegance and understated class.
How to Achieve & Maintain: Ask your barber for tapering on the sides and more length on top. Style with light wax for texture.
Recommended Products: Baxter of California Clay Pomade, Paul Mitchell Tea Tree Grooming Pomade
The Textured Quiff
A softer take on the quiff, this version emphasizes natural texture rather than excessive height.
Why It Embodies Old Money Sophistication: It strikes the perfect balance between casual ease and refined structure.
How to Achieve & Maintain: Blow-dry your hair upward using a round brush. Finish with matte paste for a tousled yet intentional look.
Recommended Products: Hanz de Fuko Claymation, Kevin Murphy Rough.Rider
The Classic Taper Fade
A gradual fade from longer hair on top to shorter sides creates a clean, professional appearance.
Why It Embodies Old Money Sophistication: Its simplicity makes it adaptable for both formal occasions and everyday wear.
How to Achieve & Maintain: Request a medium fade and keep the top neatly styled. Use a light styling cream for a natural finish.
Recommended Products: O’Douds Styling Cream, Bumble and bumble Sumotech
The Pompadour
Characterized by voluminous hair swept back from the forehead, the pompadour adds drama without sacrificing class.
Why It Embodies Old Money Sophistication: Popularized by icons like Elvis Presley, it combines boldness with timeless appeal.
How to Achieve & Maintain: Blow-dry your hair backward and apply a firm-hold pomade. Use a comb for definition.
Recommended Products: Murray’s Superior Pomade, Imperial Barber Products Medium Hold Pomade
The Brushed-Up Style
Hair is brushed straight up and slightly forward, creating volume and movement.
Why It Embodies Old Money Sophistication: It’s practical yet stylish, offering a youthful yet dignified vibe.
How to Achieve & Maintain: Apply mousse before blow-drying upward. Finish with a flexible-hold spray.
Recommended Products: Redken Brews Grip Tight Gel Pomade, Moroccanoil Molding Cream
The Caesar Cut
Short all over with bangs styled forward, the Caesar cut is minimalist yet striking.
Why It Embodies Old Money Sophistication: Its ancient Roman origins give it historical gravitas, while its simplicity aligns with Old Money values.
How to Achieve & Maintain: Keep it blunt-cut and even. Use a lightweight pomade for subtle control.
Recommended Products: Aveda Men Pure-Formance Grooming Clay, Davines This Is A Shaping Cream
The Classic Buzz Cut
Uniformly short hair across the scalp, easy to maintain and incredibly neat.
Why It Embodies Old Money Sophistication: It reflects discipline and practicality—a hallmark of Old Money ideals.
How to Achieve & Maintain: Visit your barber regularly for touch-ups. No product needed!
Recommended Products: None required
The French Crop
Short on the sides and back with textured fringe falling forward onto the forehead.
Why It Embodies Old Money Sophistication: Its European influence lends an air of cosmopolitan elegance.
How to Achieve & Maintain: Ask for a slight taper on the sides and choppy layers on top. Use sea salt spray for texture.
Recommended Products: Bumble and bumble Surf Spray, Not Your Father’s Salt Spray
The Gentleman’s Comb Over
Hair is combed to one side, often with a slight wave or curl.
Why It Embodies Old Money Sophistication: Think Cary Grant or Gregory Peck—this style radiates gentlemanly charm.
How to Achieve & Maintain: Use a wide-tooth comb and a shiny pomade for a smooth finish.
Recommended Products: Crown Shaving Co. Matte Pomade, Captain Fawcett’s Styling Pomade
The High Fade
Sharp fading begins higher on the head, leaving ample room for styling the top section.
Why It Embodies Old Money Sophistication: When paired with a neat top, it maintains a sophisticated silhouette.
How to Achieve & Maintain: Focus on keeping the fade crisp and the top styled with pomade or clay.
Recommended Products: Reuzel Fiber Pomade, Jack Black Wax Pomade
The Modern Bowl Cut
Updated with soft edges and layered texture, this version avoids the retro stiffness of traditional bowl cuts.
Why It Embodies Old Money Sophistication: Its unique shape commands attention while staying within boundaries of propriety.
How to Achieve & Maintain: Work with a skilled stylist to ensure layers blend seamlessly. Use a light cream for separation.
Recommended Products: Oribe Matte Waves Texture Lotion, R+Co Rockaway Salt Spray
The Military Fade
Extremely short on the sides and back with a tapered transition to slightly longer hair on top.
Why It Embodies Old Money Sophistication: Rooted in tradition, it conveys authority and reliability.
How to Achieve & Maintain: Regular visits to the barber are key. Style with a matte finish product if desired.
Recommended Products: Rudy’s Barbershop Pomade, Malin + Goetz Sage Styling Cream
The Natural Messy Look
Emphasizing organic texture, this style looks intentionally undone but still put-together.
Why It Embodies Old Money Sophistication: Effortlessness is central to the Old Money ethos, making this ideal.
How to Achieve & Maintain: Scrunch damp hair with a towel and apply texturizing spray. Let air dry.
Recommended Products: Ouai Texturizing Hair Spray, Living Proof Flex Shaping Hairspray
The Two-Block Cut
Longer hair on top contrasts sharply with closely cropped sides and nape.
Why It Embodies Old Money Sophistication: Though trendy, its clean execution keeps it rooted in classic principles.
How to Achieve & Maintain: Opt for regular trims and use pomade for a tidy top.
Recommended Products: Proraso Pomade, Truefitt & Hill Grafton Pomade
The Spiky Crop
Short, spiky strands stand upright for a playful yet refined effect.
Why It Embodies Old Money Sophistication: Its controlled chaos suggests creativity balanced by restraint.
How to Achieve & Maintain: Apply gel or mousse and blow-dry upwards.
Recommended Products: Kérastase Homme Capital Force Gel, Schwarzkopf OSiS Thrill
The Wavy Center Part
Naturally wavy hair parted down the middle for a relaxed yet elegant appearance.
Why It Embodies Old Money Sophistication: It channels old Hollywood glamour effortlessly.
How to Achieve & Maintain: Enhance waves with curl-enhancing cream and let air dry.
Recommended Products: DevaCurl SuperCream Coconut Curl Styler, SheaMoisture Coconut & Hibiscus Curl Enhancing Smoothie
The Preppy Crew Cut
Short, uniform length all over with minimal styling required.
Why It Embodies Old Money Sophistication: Associated with prep schools and country clubs, it epitomizes understated class.
How to Achieve & Maintain: Trim regularly and keep it simple—no products necessary.
Recommended Products: None required
The Long, Layered Flow
Shoulder-length hair with layers for movement and dimension.
Why It Embodies Old Money Sophistication: Reserved for those who dare to break norms while retaining grace.
How to Achieve & Maintain: Invest in quality conditioner and anti-frizz serum. Style loosely with fingers.
Recommended Products: Olaplex No. 6 Bond Smoother, Moroccanoil Treatment
Old Money hairstyles aren’t just about looking good—they’re about embodying a lifestyle steeped in tradition, elegance, and quiet confidence.
Whether you prefer the structured precision of a side part or the effortless charm of tousled waves, these timeless looks will help you master the art of refined masculinity.
Remember, consistency is key: invest in quality products, visit your barber regularly, and embrace the philosophy that true style transcends fleeting trends.