25 Dapper 1920s Hairstyles for Men That Bring Back Classic Vintage Style

The Roaring Twenties weren’t just about jazz, speakeasies, and Gatsby-style glam they were also a golden era for men’s grooming. With their polished finishes, sharp parts, and slicked-back charm, 1920s hairstyles offered a level of elegance and sophistication that’s still admired today. Whether you’re into vintage fashion or just want a clean, classic look, these old-school styles are making a major comeback in the modern grooming world.

This article dives deep into 25 iconic 1920s men’s hairstyles that define vintage dapper style with modern tips to make them wearable today.

Why 1920s Hairstyles Are Back in Style

The 1920s were a decade of transformation and confidence and the hairstyles reflected that. Here’s why they’re trending again:

• Timeless Sophistication: These cuts exude refinement, structure, and clean edges.
• Perfect for Formal Looks: Ideal for weddings, black-tie events, or upscale settings.
• Easy to Modernize: Add a fade, beard, or texture for a fresh twist on vintage.
• Low Maintenance: Most styles are structured and stay put with a little product.

25 Dapper 1920s Hairstyles for Men In 2025

1. Classic Side Part

The Classic Side Part is the undisputed gentleman’s hairstyle of the 1920s clean, confident, and enduring. With short, tapered sides and a longer top neatly parted to one side, this style exudes timeless class. Whether you’re heading to a formal event or channeling vintage vibes for everyday wear, the side part remains a staple of sharp sophistication.

• Key Features:
  
  • Defined side part (hard or soft)
    
  • Tapered or faded sides with length on top
    
  • Slicked using pomade for shine and control
    
• Styling Tip:
  Apply a high-hold pomade to damp hair, then use a fine-tooth comb to draw a precise part and smooth the top into place for a sleek, polished finish.
  
• Best For:
  
  • Straight to slightly wavy hair
    
  • Oval, square, or heart-shaped faces
    
  • Men seeking a structured, classic look
    
• Vibe:
  
  • Sharp and distinguished
    
  • Elegant vintage charm
    
  • Everyday Gatsby-approved
    

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2. Slicked Back Hair

The Slicked Back look was a signature style of the roaring twenties, favored by businessmen, jazz artists, and gangsters alike. This ultra-smooth style keeps all hair combed back with shine and structure. It’s versatile enough for both straight and wavy hair and pairs effortlessly with suits, suspenders, or a modern vintage wardrobe.

• Key Features:
  
  • Hair combed straight back from the hairline
    
  • High-gloss texture using gel or pomade
    
  • Uniform flow that flatters most head shapes
    
• Styling Tip:
  Apply gel or a shine-enhancing pomade to damp hair and comb it all backward with even pressure. For extra hold, finish with a light mist of hairspray.
  
• Best For:
  
  • Straight or wavy hair with medium density
    
  • Oval, oblong, or square face shapes
    
  • Men who prefer a bold, refined aesthetic
    
• Vibe:
  
  • Dashing and suave
    
  • Retro refinement
    
  • Smooth, prohibition-era polish

3. Finger Waves for Men

Finger waves weren’t just for flapper girls this artistic, sculpted hairstyle was also sported by stylish men in the 1920s, especially entertainers and trendsetters. Featuring elegant S-shaped curves, finger waves give your hair a sleek, formal look with plenty of vintage flair. It’s an ideal throwback style for themed events, fashion-forward shoots, or men with medium-length hair who appreciate a detailed aesthetic.

• Key Features:
  
  • Defined S-shaped wave patterns
    
  • High-shine, sculpted finish
    
  • Best suited for medium-length hair
    
• Styling Tip:
  Apply a strong-hold gel to damp hair. Using a fine-tooth comb and your fingers, mold the waves into shape. Let them air dry to preserve structure and sheen.
  
• Best For:
  
  • Straight or relaxed hair types
    
  • Men with medium hair length and artistic taste
    
  • Formal events, costume parties, or vintage fashion
    
• Vibe:
  
  • Artistic and expressive
    
  • Retro-glam meets old Hollywood
    
  • Bold, standout sophistication
    

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4. The Tidy Crop

A classic choice for the everyman of the 1920s, The Tidy Crop features a clean, short, and low-maintenance cut that still looks structured and neat. With short length all around and a subtle side part, this haircut was a favorite for factory workers, office clerks, and gents who valued practicality over pomp. It’s simple, timeless, and still relevant today.

• Key Features:
  
  • Uniform short length with slight tapering
    
  • Optional soft side part for subtle shape
    
  • Easy to maintain and style daily
    
• Styling Tip:
  Rub a matte paste between your hands and run it through dry or slightly damp hair to add a hint of texture and hold without making it look overdone.
  
• Best For:
  
  • All hair types, especially straight and wavy
    
  • Round or oval faces
    
  • Men who prefer clean, low-effort grooming
    
• Vibe:
  
  • No-nonsense and classic
    
  • Clean-cut and gentlemanly
    
  • Understated vintage cool
    

5. Gatsby Comb Back

Named after the iconic Jay Gatsby, this comb-back hairstyle is the epitome of 1920s opulence and elegance. The longer top is swept straight back, giving the look both structure and drama, while the neatly tapered sides maintain balance and polish. Whether you’re heading to a formal event or just want a touch of literary-inspired class, this style captures the spirit of the Jazz Age.

• Key Features:
  
  • Medium to long top combed backward
    
  • Tidy, shorter sides with a clean neckline
    
  • Sleek, formal, and highly refined
    
• Styling Tip:
  Blow dry the top while brushing it straight back to create height, then apply a high-shine pomade or styling cream to lock it in with a smooth finish.
  
• Best For:
  
  • Straight or slightly wavy hair
    
  • Oval, heart, or square face shapes
    
  • Special events, Gatsby parties, or retro dress codes
    
• Vibe:
  
  • Elegant and charismatic
    
  • Jazz Age luxury
    
  • Bookish with a bold edge
    

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6. Pompadour with Side Part

Combining the volume of a pompadour with the structure of a traditional side part, this style delivers a refined twist on a 1920s classic. The height in front draws attention upward, elongating the face and adding instant sophistication. Paired with cleanly tapered sides, this cut radiates a high-society, boardroom-meets-ballroom energy.

• Key Features:
  
  • Elevated pompadour front
    
  • Sharp side part for definition
    
  • Tapered or faded sides for balance
    
• Styling Tip:
  Use a round brush while blow-drying the top section upward and back. Follow up with a volumizing mousse or pomade to maintain shape and shine.
  
• Best For:
  
  • Medium-thick straight or wavy hair
    
  • Round or oval faces needing height
    
  • Men who want vintage flair with runway-level structure
    
• Vibe:
  
  • Bold and distinguished
    
  • Classic with elevated flair
    
  • Polished gent with vintage power

7. Wet Look with Gloss

The Wet Look was a defining statement of the 1920s sleek, sharp, and undeniably sophisticated. With hair slicked down uniformly and styled close to the scalp, this style offers a polished silhouette that screams vintage charm. The glossy finish reflects light beautifully, giving the hair a luxurious, well-groomed appearance that was especially popular among men attending evening affairs or performing on stage.

• Key Features:
  
  • Uniformly slicked down from front to back
    
  • High-shine, wet-look finish
    
  • Best suited for oval or long face shapes
    
• Styling Tip:
  Use a gel or oil-based pomade on damp hair, then comb flat with precision. Avoid matte products, as they dull the look shine is essential.
  
• Best For:
  
  • Straight or relaxed hair types
    
  • Men who favor sleek, formal aesthetics
    
  • Special occasions or themed parties
    
• Vibe:
  
  • Glossy and composed
    
  • Dramatic vintage polish
    
  • Hollywood crooner charm
    

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8. Short Back and Sides

A barbershop classic that dominated the 1920s, the Short Back and Sides is a versatile, clean-cut hairstyle that’s stood the test of time. It features neatly trimmed sides and a slightly longer top that can be styled or left natural. This was the everyday man’s haircut refined but easy to maintain, and still favored by stylish men today.

• Key Features:
  
  • Short, tapered sides and back
    
  • Slight length left on top for styling options
    
  • Clean, structured neckline
    
• Styling Tip:
  Request a soft taper or scissor cut at the barbershop to achieve an authentic 1920s look. Use a dab of matte paste or pomade to add light control.
  
• Best For:
  
  • All hair types
    
  • Round, square, or oval face shapes
    
  • Men who value simplicity with a sharp finish
    
• Vibe:
  
  • Timeless and practical
    
  • Understated gentleman
    
  • Clean barbershop style

9. The Ivy League

Though often associated with the 1940s, the Ivy League’s roots trace back to the late 1920s. This hairstyle bridges academic polish and dapper flair, making it perfect for men who prefer structure without sacrificing personality. With a neatly side-swept top and clean, short sides, the Ivy League embodies understated charm and timeless refinement.

• Key Features:
  
  • Short sides with slightly longer, side-swept top
    
  • Structured silhouette with clean lines
    
  • Collegiate, polished, and adaptable
    
• Styling Tip:
  Apply a light cream or pomade to damp hair and comb to the side for soft control. Pairs perfectly with a blazer or tailored look for a complete gentleman’s vibe.
  
• Best For:
  
  • Straight to wavy hair
    
  • Oval or square face shapes
    
  • Men looking for versatile, professional style
    
• Vibe:
  
  • Educated and refined
    
  • Low-key vintage prep
    
  • Campus cool meets cocktail hour
    

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10. Brushed Back Waves

For men with natural texture, Brushed Back Waves offer a relaxed take on 1920s sophistication. This style embraces mid-length waves, swept gently away from the face to create movement and character. It’s ideal for those who prefer a more laid-back vintage aesthetic while still looking intentional and polished.

• Key Features:
  
  • Medium length on top and sides
    
  • Gentle, natural wave pattern
    
  • Flowy and textural
    
• Styling Tip:
  Use a sea salt spray on damp hair to enhance wave definition, then brush backward loosely with your fingers or a wide-tooth comb for a natural finish.
  
• Best For:
  
  • Wavy or slightly curly hair types
    
  • Men with medium hair length
    
  • Casual wearers of vintage-inspired looks
    
• Vibe:
  
  • Artistic and relaxed
    
  • Soft, romantic elegance
    
  • Vintage flair with coastal cool

11. Clean Taper with Mustache Combo

Nothing says 1920s gentleman quite like a sharp taper haircut paired with a meticulously groomed mustache. This combo was a favorite among well-dressed men, especially those who frequented speakeasies and jazz clubs. The clean taper adds structure and modern edge, while the mustache offers a hint of roguish flair and vintage confidence.

• Key Features:
  
  • Gradual taper around the sides and back
    
  • Thin, shaped mustache for facial definition
    
  • Sophisticated, high-society appeal
    
• Styling Tip:
  Keep both the taper and mustache trimmed regularly. Use a light styling cream for your hair and a dab of mustache wax to keep things looking tidy not overpowering.
  
• Best For:
  
  • Straight or wavy hair
    
  • Oval, square, or long face shapes
    
  • Men who want to pair hair and facial grooming for full effect
    
• Vibe:
  
  • Suave and deliberate
    
  • Great Gatsby meets classic noir
    
  • Refined and rakish
    

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12. Center Part with Shine

Though the side part reigned supreme in the 1920s, the center part had its niche often worn by bohemian artists, film stars, and men on the cutting edge of style. With symmetrical balance and a sleek finish, this look conveys artistic confidence and nonconformist elegance.

• Key Features:
  
  • Sharp center part running front to back
    
  • Mid to long hair on both sides for drape
    
  • Clean, glossy texture
    
• Styling Tip:
  Apply a lightweight pomade or gloss-enhancing cream to damp hair, then part precisely down the middle using a fine-tooth comb. Avoid overloading with product to keep the look fresh, not greasy.
  
• Best For:
  
  • Medium to long hair lengths
    
  • Oval or symmetrical face shapes
    
  • Creative or performance-driven styles
    
• Vibe:
  
  • Avant-garde and artsy
    
  • Daring yet debonair
    
  • Silent film star elegance

13. The Gentleman’s Fade (Modern Twist)

Blending modern technique with vintage aesthetics, the Gentleman’s Fade updates the classic 1920s parting style with a clean, tapered fade. The slick top remains true to the era, but the high or mid fade adds a fresh edge making it ideal for men who want a nod to the past with a current twist.

• Key Features:
  
  • High or mid fade on the sides and back
    
  • Hard or soft side part
    
  • Glossy, combed-over top
    
• Styling Tip:
  Use a strong-hold pomade to comb the top into place while the fade is freshly cut. Touch up the fade every couple of weeks to maintain sharpness.
  
• Best For:
  
  • Straight or slightly wavy hair
    
  • Round or square face shapes
    
  • Men who want modern polish with vintage influence
    
• Vibe:
  
  • Dashing and contemporary
    
  • Refined edge
    
  • Gentleman with a modern twist
    

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14. Tight Slick Undercut

While less common in the mainstream 1920s crowd, the tight slick undercut was favored by men on the style fringe think avant-garde artists or rebellious jazz musicians. The stark contrast between the shaved sides and slicked-back top gives this style a bold, head-turning energy that still channels vintage structure.

• Key Features:
  
  • Very short or shaved sides
    
  • Longer top slicked back tightly
    
  • High-contrast, edgy silhouette
    
• Styling Tip:
  Apply a strong-hold pomade or gel to keep the top slick and in place all day. This style also works well with hats or fedoras, making it ideal for both formal and fashion-forward wearers.
  
• Best For:
  
  • Medium to thick hair
    
  • Heart or oval-shaped faces
    
  • Men who want vintage vibes with dramatic flair
    
• Vibe:
  
  • Bold and daring
    
  • Speakeasy rebel
    
  • Classic structure with a fashion punch

15. The Barber’s Standard

This was the go-to haircut for the everyman of the 1920s clean, conservative, and built for low maintenance. Known for its rounded shape and blunt neckline, the Barber’s Standard was a staple in neighborhood barbershops across America. It’s perfect for men who want a vintage-inspired style without the need for heavy product or styling.

• Key Features:
  
  • No defined part
    
  • Rounded, even top
    
  • Tapered or blunt neckline for a classic finish
    
• Styling Tip:
  Keep the look tight and sharp with regular trims every 2–3 weeks. Use a small amount of matte cream to smooth down flyaways if needed.
  
• Best For:
  
  • All hair types
    
  • Oval or round face shapes
    
  • Men who prefer no-fuss grooming
    
• Vibe:
  
  • Clean and traditional
    
  • Blue-collar charm
    
  • Timeless barbershop classic
    

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16. Smooth Crown Fade (Modern Vintage)

Bridging the past and present, the Smooth Crown Fade features a bald or skin fade that rises cleanly into a slicked-back crown. This modern take mimics military-inspired cuts of the 1920s while adding today’s fade precision. With a high-gloss top and seamless blend, it’s crisp, bold, and full of gentlemanly swagger.

• Key Features:
  
  • Bald or skin fade low on the sides
    
  • Combed crown top with shine
    
  • Modern meets vintage silhouette
    
• Styling Tip:
  Use a dome-style application with a high-shine pomade to slick the crown back and enhance the polished finish. Maintain the fade every two weeks for best results.
  
• Best For:
  
  • Straight or fine hair
    
  • Square or angular face shapes
    
  • Men who want a military-vintage fusion
    
• Vibe:
  
  • Sharp and disciplined
    
  • Regal with a tough edge
    
  • Classic soldier meets speakeasy style
    

17. Textured Side Part

Not every 1920s style required a high-shine finish. The Textured Side Part brings a modern, dry take on a classic gentleman’s cut. Instead of pomade, matte clay gives this style visible definition and natural movement. It’s perfect for men who want vintage charm without the gloss.

• Key Features:
  
  • Clearly defined side part
    
  • Visible layers and texture
    
  • Natural, no-shine finish
    
• Styling Tip:
  Use a matte clay or fiber product on dry hair to separate layers and add grit. Work in small sections to keep the part clean and structured without stiffness.
  
• Best For:
  
  • Thick or wavy hair
    
  • Round or oval faces
    
  • Men who prefer a casual, modern-vintage hybrid
    
• Vibe:
  
  • Understated and classic
    
  • Editorial-ready
    
  • Vintage style with a contemporary twist
    

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18. Short Waves with Defined Hairline

A standout style among Black men in the 1920s, Short Waves with a Defined Hairline offered texture, elegance, and cultural pride. The wave pattern adds depth while a crisp line-up around the forehead and temples gives this look unmistakable polish. It’s a timeless cut that’s as bold today as it was in the jazz age.

• Key Features:
  
  • Natural wave pattern (360 or short waves)
    
  • Sharp edge-up or shape-up at the hairline
    
  • Smooth, well-brushed texture
    
• Styling Tip:
  Apply wave cream daily and brush in the same direction to maintain definition. A durag at night will help set waves and preserve the look.
  
• Best For:
  
  • Coarse or curly hair
    
  • Round, square, or heart-shaped faces
    
  • Men who want clean structure with rich texture
    
• Vibe:
  
  • Elegant and proud
    
  • Sophisticated with cultural depth
    
  • A jazz-era essential

19. Short Pompadour with Tapered Neck

For a more subtle nod to the roaring ’20s, the Short Pompadour with Tapered Neck maintains a clean, controlled profile without the dramatic height. This look offers just enough lift to reflect classic pompadour style while keeping the neckline neat and low-maintenance. It’s polished, versatile, and great for everyday wear.

• Key Features:
  
  • Lightly elevated front section
    
  • Tapered neckline for a soft finish
    
  • Minimalist pompadour aesthetic
    
• Styling Tip:
  Blow-dry the top for gentle lift, then apply a medium-hold cream or mousse for flexible control without stiffness.
  
• Best For:
  
  • Straight or slightly wavy hair
    
  • Oval or oblong face shapes
    
  • Men looking for a vintage style that’s not too flashy
    
• Vibe:
  
  • Classic and approachable
    
  • Office-to-evening ready
    
  • A restrained twist on 1920s volume
    

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20. Disconnected Side Part

The Disconnected Side Part takes a sharper, bolder approach to 1920s styling. A razor-defined part line cleanly separates the slicked-back top from faded or shaved sides, creating striking contrast and modern edge. It’s one of the most eye-catching ways to channel vintage class with current flair.

• Key Features:
  
  • Strong hard part or shaved line
    
  • High-contrast separation between top and sides
    
  • Slicked back or combed-over top section
    
• Styling Tip:
  Ask your barber to maintain the hard part regularly. Use pomade or gel to keep the top clean, slick, and defined.
  
• Best For:
  
  • Medium to thick hair
    
  • Square or angular faces
    
  • Men who want standout structure
    
• Vibe:
  
  • Bold and intentional
    
  • High-definition vintage
    
  • Classic style with modern grit

21. The Modest Gentleman’s Cut

The Modest Gentleman’s Cut is understated elegance at its finest. This style doesn’t rely on dramatic parts, volume, or heavy product. Instead, it keeps the length uniform and structured, perfect for men who value simplicity and age-appropriate sophistication. It was popular among older gents in the 1920s who embraced timeless, no-fuss grooming.

• Key Features:
  
  • Even-length all over
    
  • No defined part or lift
    
  • Clean edges and soft silhouette
    
• Styling Tip:
  Apply a lightweight styling cream or lotion to keep everything neat without stiffness. Ideal for daily wear and low-maintenance routines.
  
• Best For:
  
  • Mature men
    
  • Thin or fine hair types
    
  • Those who prefer minimal upkeep
    
• Vibe:
  
  • Quiet confidence
    
  • Age-appropriate refinement
    
  • Classic with effortless charm
    

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22. Comb-Over with Clean Sides

Forget the cliché this Comb-Over with Clean Sides isn’t about hiding hair loss. It’s a deliberate and dapper 1920s look that features a voluminous sweep to one side, balanced with a neatly trimmed neckline and sides. When styled with precision, it delivers a look of elegance and control.

• Key Features:
  
  • Strong side-sweep or part
    
  • Tidy nape and side taper
    
  • Ideal for formal or business attire
    
• Styling Tip:
  Blow-dry the top in the direction of your natural part to lock in the shape, then apply a lightweight pomade for hold and shine.
  
• Best For:
  
  • Straight or wavy hair
    
  • Oval or round face shapes
    
  • Men who want structure with class
    
• Vibe:
  
  • Refined and intentional
    
  • Vintage sophistication
    
  • Suit-and-tie ready
    

23. Pencil-Styled Back Hair

The Pencil-Styled Back Hair was a sharp, slicked-back favorite among 1920s entertainers and high-society personalities. This look is all about straight lines, flat structure, and high shine resembling a finely drawn silhouette. It delivers a polished, clean finish that photographs beautifully and commands attention.

• Key Features:
  
  • Razor-straight slick-back
    
  • Low-profile cut, tight to the scalp
    
  • Mirror-like gloss finish
    
• Styling Tip:
  Use a high-shine gel while hair is damp, then comb it flat and finish with hairspray for a firm, all-day hold.
  
• Best For:
  
  • Straight hair
    
  • Oval or angular faces
    
  • Men seeking a dramatic, camera-ready vintage look
    
• Vibe:
  
  • Performer’s flair
    
  • Sleek and formal
    
  • Glamorous and red-carpet ready
    

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24. Gentlemen’s Mop with Structure

A looser interpretation of 1920s style, the Gentlemen’s Mop with Structure offers texture, medium length, and subtle volume without looking unkempt. It balances casual and tailored, ideal for expressive men who want vintage charm without stiffness.

• Key Features:
  
  • Medium-length, tousled look
    
  • Layered top with relaxed side flow
    
  • Easy to reshape or part naturally
    
• Styling Tip:
  Apply a lightweight mousse or cream, then finger-style for an intentionally undone look with volume and flow.
  
• Best For:
  
  • Thick or wavy hair
    
  • Square or round face shapes
    
  • Men who want vintage flair with creative freedom
    
• Vibe:
  
  • Artistic and laid-back
    
  • Vintage with a twist
    
  • Casual sophistication
    

25. Vintage Military Crew

The Vintage Military Crew draws inspiration from the neat, practical cuts worn by servicemen in the 1920s. With nearly buzzed sides and just a hint of length on top, this cut offers masculine minimalism at its finest. It’s clean, sharp, and effortlessly timeless perfect for men who prefer zero fuss without sacrificing style.

• Key Features:
  
  • Ultra-short sides and back
    
  • Slightly longer top
    
  • Clean lines with a rugged edge
    
• Styling Tip:
  No product necessary just schedule regular trims every 2–3 weeks to keep the look crisp and precise.
  
• Best For:
  
  • All hair types
    
  • Active lifestyles
    
  • Men who want a tough, no-nonsense style
    
• Vibe:
  
  • Military precision
    
  • Masculine and utilitarian
    
  • Effortless classic cool