Stepping into the world of vintage hairstyles is like taking a trip back in time to an era where elegance and sophistication reigned supreme.
Old money fashion isn’t just about clothing—hairstyles play an equally crucial role in curating that timeless look.
From slicked-back classics to charming waves, these hairstyles are not only elegant but also exude confidence and charm.
Ready to elevate your style game? Let’s explore 44 dapper hairstyles that will make you feel like a million bucks, blending old-world charm with modern flair.
Contents
- 1. The Classic Side Part
- 2. The Slicked-Back Look
- 3. The Pompadour
- 4. The Ivy League Cut
- 5. The Taper Fade
- 6. The Curly Top
- 7. The Gentleman’s Quiff
- 8. The Old Hollywood Wave
- 9. The Classic French Crop
- 10. The 1940s Side Part
- 11. The Buzz Cut
- 12. The Longer Top with Short Sides
- 13. The Textured Fringe
- 14. The Brushed Up Style
- 15. The Classic Crew Cut
- 16. The Long Hair with Tucked Behind the Ear
- 17. The Side-Swept Bangs
- 18. The Natural Texture
- 19. The Vintage Bowl Cut
- 20. The Edwardian Inspired Style
- 21. The Modern Caesar Cut
- 22. The Vintage Undercut
- 23. The Long and Loose Waves
- 24. The Retro Pompadour Fade
- 25. The Messy Chic Look
- 26. The Long Side Part
- 27. The Long Beard and Hair Combo
- 28. The Sophisticated Long Ponytail
- 29. The Wild Rockabilly Style
- 30. The Old School Bowl with Fade
- 31. The Tightly Styled Pompadour
- 32. The Loose, Natural Look
- 33. The Classic Taper
- 34. The Distinguished Long Lock
- 35. The Casual Half-Up Style
- 36. The Refined Slick Side
- 37. The Elegant Low Bun
- 38. The Sharp Edges with Long Top
- 39. The Fashionable Mullet
- 40. The Vintage Textured Crop
- 41. The Classic Long Hair with Waves
- 42. The Sharp Business Look
- 43. The Dapper Faded Comb Over
- 44. The Timeless Tucked Look
1. The Classic Side Part

The classic side part is a hallmark of timeless elegance and masculinity.
This hairstyle works beautifully with various hair types and lengths, making it incredibly versatile.
To nail this look, begin by ensuring your hair is clean and slightly damp. Apply a styling pomade or wax for hold, and use a comb to create a defined part on one side.
For a polished finish, blow-dry your hair while combing it to the side. This style pairs perfectly with a tailored suit or casual wear, giving off an effortlessly sophisticated vibe.
Pro tip: For added texture, try using a sea salt spray before styling for that perfect beachy wave effect.
2. The Slicked-Back Look

Slicked-back hairstyles ooze confidence and charm and are a favorite among the old money elite.
This style is all about control and shine, achieved through quality hair products. Start with damp hair, applying a generous amount of pomade or gel.
Use a comb to slick back your hair from the forehead to the nape, ensuring no stray hairs are left behind.
For a modern twist, consider adding a fade or undercut on the sides. This look is ideal for formal occasions but can be dressed down with a casual shirt for a night out.
Remember, the key to a polished slicked-back style is patience—give your hair time to set before venturing out to flaunt your refined look.
3. The Pompadour

Ah, the pompadour—a style that has withstood the test of time and remains a symbol of sophistication.
This hairstyle is characterized by volume and height at the front, tapering down the sides. To achieve this look, apply a volumizing mousse to damp hair, then blow-dry while lifting the hair at the roots.
Once dry, use pomade to sculpt and define the front, making sure it maintains that classic lift.
This is an eye-catching style that pairs well with sharp suits and can be transformed to suit more casual settings by toning down the height.
Consider adding some texture with a texturizing spray for a more relaxed vibe.
4. The Ivy League Cut

The Ivy League cut is a timeless hairstyle that reflects a smart, polished persona.
This hairstyle combines short sides with a bit more length on top, allowing for versatility in styling.
To achieve this look, ask your barber for a clean cut with tapered sides and leave enough length on top to style with a side part or slicked back.
This cut works excellently for both professional and casual environments, maintaining an air of sophistication.
Add a touch of pomade for a neat finish, and consider keeping your beard well-groomed to complement this classic style.
5. The Taper Fade

The taper fade is a modern yet classic choice that adds a fresh twist to vintage styles.
This look allows for longer hair on top while gradually shortening the hair on the sides and back.
To get this style, start with a trim on the top, maintaining enough length for versatility. Gradually fade the sides, blending the transition smoothly.
This haircut is highly adaptable; style it slicked back, textured, or even with a messy look for an effortless vibe.
Accessorize with a watch or elegant cufflinks to enhance the overall appearance, making this style perfect for a day at the office or a night out.
6. The Curly Top

For those blessed with natural curls, the curly top is a standout choice that celebrates texture and volume.
Embrace your natural curl pattern by getting a haircut that keeps the sides short while allowing the top to flourish.
Use a curl cream or mousse to define your curls while keeping them frizz-free.
This style projects a laid-back yet sophisticated vibe, perfect for casual outings or semi-formal events.
Pair it with a button-up shirt or a cashmere sweater for a look that feels both relaxed and refined.
7. The Gentleman’s Quiff

A gentleman’s quiff is all about balance, combining retro elements with a touch of modern flair.
This hairstyle features longer hair at the front styled upwards and back, while the sides can be short or tapered.
Start by applying a volumizing product to damp hair and blow-dry it to create body. Then, use a comb to shape the quiff, adjusting the height to your preference.
This style is fantastic for formal occasions or casual evenings out, pairing well with a tailored blazer or a knitted sweater.
To keep the quiff intact all day, finish with a light spray of hairspray for hold without stiffness.
8. The Old Hollywood Wave

Channel your inner movie star with the old Hollywood wave, a hairstyle that screams glamour and sophistication.
This style features soft, structured waves that frame the face elegantly. Start by curling sections of hair with a large barrel curling iron, then pin each curl to set while cooling.
Once cooled, gently brush through the curls to create soft waves, securing with a light-hold spray.
Perfect for events and gatherings, this hairstyle pairs beautifully with a tuxedo or a fitted suit.
Consider adding a bow tie for an extra dash of old-school charm and sophistication.
9. The Classic French Crop

The French crop is an understated yet stylish choice that offers a refined look without fuss.
This hairstyle features short sides and a slightly longer top, where the hair is cropped just above the forehead.
To style, apply a light texturizing cream and tousle the top to create a relaxed but polished look.
Ideal for those who prefer low-maintenance hair, the French crop works well with any outfit, from business casual to weekend wear.
Finish with a bit of product to keep it looking fresh throughout the day.
10. The 1940s Side Part

The 1940s side part is a vintage hairstyle that embodies classic masculinity and style.
This look features a deep side part with slicked-back hair on one side, paired with a smooth finish.
To achieve this, use a high-quality pomade to maintain its sleek appearance while combing the hair to one side.
This hairstyle aligns perfectly with vintage-inspired suits, often seen accessorized with a fedora or bow tie.
It’s a great option for formal events or stylish day-to-day wear, exuding confidence in every aspect.
11. The Buzz Cut

For the minimalist at heart, the buzz cut is a timeless choice that highlights facial features.
This clean and simple style involves clipping the hair to a uniform length all around, creating a no-nonsense look.
Though it requires little maintenance, it can still be elevated with the right grooming—think clean lines and a fresh shave.
This style pairs well with a variety of outfits, making it perfect for both casual and formal occasions.
Add a statement watch or accessory to enhance your outfit and make a bold impression.
12. The Longer Top with Short Sides

This hairstyle strikes a balance between modern and vintage vibes by keeping the top longer while tapering the sides.
It offers versatility as you can style it slicked back, textured, or messy, depending on the occasion.
To maintain this look, apply a bit of pomade to the damp hair on the top and let your stylist keep the sides short but blended.
It’s the perfect style for a suave look that transitions seamlessly from day to night.
Accessorizing with a sharp blazer or a stylish watch can really pull this look together.
13. The Textured Fringe

The textured fringe hairstyle is a choice that adds a youthful edge to vintage-inspired looks.
This style features longer hair at the front styled forward to create a relaxed, textured effect.
To achieve this look, apply a lightweight styling cream and use your fingers to tousle the hair, enhancing its natural movement.
It works fabulously with smart-casual attire and can be dressed up with a blazer or down with a simple t-shirt.
For a uniquely rugged touch, consider incorporating a well-groomed beard for added character.
14. The Brushed Up Style

The brushed-up style is a modern take on vintage elegance, perfect for both formal and casual settings.
This hairstyle features hair that is brushed upwards and back, creating a clean, polished look.
To create this style, start with damp hair and apply a volumizing product, then blow-dry while brushing the hair upward.
This look is chic and works exceptionally well with tailored outfits, evoking a polished appearance that commands attention.
To keep the style intact, use a strong-hold product to maintain that fresh-out-of-the-barber look all day.
15. The Classic Crew Cut

The crew cut is a quintessentially classic style that symbolizes discipline and neatness.
With short hair on the sides and slightly more length on top, this cut is easy to maintain and style.
Use a bit of gel or pomade to define the top and keep the sides looking sharp.
It pairs well with any outfit, making it a versatile choice for everyday wear.
For an added touch of sophistication, consider pairing it with a well-fitted blazer or a crisp white shirt for a clean look.
16. The Long Hair with Tucked Behind the Ear

For those with longer locks, tucking hair behind the ear creates a refined and polished appearance.
This style not only keeps hair out of the face but also highlights your facial features elegantly.
To achieve this look, ensure your hair is clean and styled straight, possibly with a bit of product to maintain shape.
The tucked style works beautifully with a crisp shirt and tailored trousers, making it suitable for both work and social outings.
Consider adding a subtle accessory, like an earring, for a touch of personal flair.
17. The Side-Swept Bangs

Side-swept bangs add a dynamic touch to any classic hairstyle, offering depth and interest.
This look works well with various lengths, as the bangs can transition seamlessly from short to longer styles.
To create this style, have the bangs cut at an angle and style them with a light mousse or pomade, sweeping them to one side.
This is perfect for adding a hint of youthful charm, which pairs nicely with smart-casual outfits or formal suits.
For a finishing touch, consider adding a subtle highlight to your bangs for added dimension.
18. The Natural Texture

Embracing your natural texture is a great way to maintain vintage charm while celebrating individuality.
This look allows your natural curls or waves to shine, giving off a relaxed vibe.
Use a curl-defining product or a light mousse to enhance texture while keeping frizz at bay.
This style is versatile and can be worn with a variety of outfits, from casual to semi-formal.
Consider pairing this hairstyle with a well-tailored jacket for an effortlessly sophisticated appearance.
19. The Vintage Bowl Cut

The vintage bowl cut is making a comeback, capturing a retro flair that is both nostalgic and stylish.
This hairstyle is characterized by a rounded cut that sits evenly around the head, keeping it neat and tidy.
To achieve this cut, simply ask your barber for a blunt fringe that aligns with the rest of the hair around the head.
This look is fun and can be styled with a bit of product for a modern twist, making it perfect for casual outings or fashion-forward events.
Accessorize with a vintage-inspired outfit for a complete throwback look.
20. The Edwardian Inspired Style

Channel an Edwardian gentleman with a hairstyle that reflects grandeur and opulence.
This look typically includes longer hair with soft waves, often styled to the side for a sophisticated finish.
To create this style, use a curling wand to add soft waves and a light-hold product to maintain the texture.
It’s ideal for formal events and pairs beautifully with a waistcoat or classic suit.
For a more modern take, lightly tousle the waves for a relaxed yet refined look.
21. The Modern Caesar Cut

The modern Caesar cut offers a fresh take on a classic style, maintaining a short length while allowing for some texture on top.
This cut works well for all hair types and requires minimal styling; simply apply a light pomade to enhance the texture.
This hairstyle pairs perfectly with both casual and formal attire, making it versatile for any occasion.
For a classic touch, consider adding a well-groomed beard to enhance your features.
It’s a low-maintenance yet stylish option for the contemporary gentleman.
22. The Vintage Undercut

The vintage undercut combines modern style with classic elements, allowing for creativity in how you style the top.
With short sides and longer hair on top, this hairstyle can be slicked back or left textured and messy.
To achieve this, ask your barber for a defined undercut while keeping the top long enough for versatility.
Ideal for casual outings or smart events when styled right, it’s the perfect mix of vintage charm and contemporary edge.
Finish with a quality pomade or wax for that polished look.
23. The Long and Loose Waves

Long, loose waves evoke a sense of laid-back sophistication, perfect for a casual yet elegant appearance.
This hairstyle works best with medium to long hair and can be achieved with a curling wand or by braiding damp hair overnight.
For added texture, try using a sea salt spray to enhance those beachy waves.
This style conveys a relaxed vibe that’s excellent for both casual outings and sophisticated events.
Pair it with a light linen shirt for an effortless summer look or with a structured jacket for a more polished appearance.
24. The Retro Pompadour Fade

Combining the classic pompadour with a fade creates a striking contrast that radiates confidence.
This hairstyle features a voluminous top paired with faded sides, offering a visually appealing silhouette.
To get this look, maintain height on the top while gradually fading the sides. Use a high-hold pomade to keep the top styled upwards.
This is perfect for smart events and pairs well with tailored suits, making it a go-to for modern gentlemen seeking vintage charm.
Don’t forget to groom your facial hair to complement this bold style.
25. The Messy Chic Look

Messy chic hairstyles offer a carefree vibe while still maintaining an air of sophistication.
This style features tousled hair that looks effortlessly stylish, perfect for those who prefer a more relaxed approach.
To create this look, apply a texturizing spray on damp hair and scrunch it while air-drying.
It’s ideal for casual settings yet can be dressed up for more formal occasions with the right outfit.
A casual blazer or fitted shirt can elevate this effortless style, proving that you can never go wrong with a bit of organized chaos.
26. The Long Side Part

The long side part is a classic hairstyle that lends itself nicely to various fashion statements.
This look features longer hair swept to one side, creating an elegant finish that feels timeless.
Using a quality styling cream can help maintain the part while providing texture and hold.
It’s versatile enough to pair with a blazer for a formal event or simply worn with a casual shirt for a relaxed vibe.
Consider adding a hat for a classic touch, making this style even more refined.
27. The Long Beard and Hair Combo

Combining long hair with a well-groomed beard creates a striking and sophisticated appearance.
This look emphasizes masculinity and individuality, ideal for those who want to make a statement.
Ensure your hair is healthy and well-cared for, using quality products to maintain both your hairstyle and beard.
This style pairs beautifully with casual or semi-formal outfits, creating a rugged yet refined look.
Accessorize with a bold watch or unique pendant to enhance your personal style.
28. The Sophisticated Long Ponytail

The long ponytail is a classic choice that exudes a sense of elegance and sophistication.
This hairstyle allows for versatility, as you can style it sleek or slightly tousled for a more relaxed look.
To achieve this, gather the hair at the nape of the neck and secure it with a stylish hair tie.
This hairstyle complements any outfit, from business casual to formal wear, making it a go-to for many occasions.
Consider wrapping a small section of hair around the base of the ponytail for an added touch of style.
29. The Wild Rockabilly Style

The rockabilly hairstyle showcases a playful and rebellious spirit while still keeping it stylish.
This look features voluminous hair styled upward with a distinct pompadour at the front.
Achieve this by using a strong-hold pomade and a teasing comb to create lift and texture.
This style pairs well with vintage-inspired attire, reflecting a sense of nostalgia and fun.
Accessorizing with a leather jacket or classic denim can elevate this playful style, making it suitable for events or casual outings.
30. The Old School Bowl with Fade

This style blends the classic bowl cut with modern fades for a unique and stylish appearance.
The balanced bowl cut on top creates a retro look while the fade keeps the style fresh and current.
To achieve this, ask your barber for a clean bowl cut on top, tapering the sides for a smooth finish.
This hairstyle stands out in both casual and formal settings, allowing for versatile styling.
Accessorize with a trendy outfit to complete the look, proving that vintage can indeed be modern.
31. The Tightly Styled Pompadour

For those who prefer a neat and structured appearance, the tightly styled pompadour is the perfect choice.
This look features a high pompadour with tightly combed sides, ensuring a polished and elegant finish.
To style, use a strong-hold gel or pomade, combing the hair back and upwards for maximum height.
This hairstyle is particularly suitable for formal occasions and can be paired beautifully with a tuxedo or a classic suit.
To keep everything in check, finish with hairspray for extra hold throughout the day.
32. The Loose, Natural Look

For those who love a relaxed vibe, a loose, natural hairstyle can exude both charm and sophistication.
This style embraces natural textures and can be worn down or half-up for a more sophisticated appearance.
Simply let your hair fall naturally or use a little product to enhance wave patterns.
This hairstyle is perfect for casual outings or laid-back formal events, making it a versatile option.
Pair with a simple yet elegant outfit for an effortlessly sophisticated appearance.
33. The Classic Taper

A classic taper is a go-to hairstyle that maintains a neat appearance while providing versatility for various occasions.
This hairstyle features short sides that gradually become longer on top, allowing for multiple styling options.
To achieve this look, keep the sides well-trimmed and ask for a bit more length on top for styling ease.
This hairstyle works well with casual and formal outfits, making it a universal favorite.
Finishing with a dab of product ensures your style remains fresh all day long.
34. The Distinguished Long Lock

Long locks can evoke a sense of mystery and allure when styled deliberately.
This hairstyle involves growing your hair longer while keeping it well-groomed and tidy.
For maintenance, regular trims are essential to keep the ends healthy and styled.
This look pairs well with formal and casual outfits, allowing for elegant diversity.
Consider incorporating subtle layers for added movement and texture throughout the hair.
35. The Casual Half-Up Style

The casual half-up style offers a laid-back vibe while still being polished enough for various occasions.
This hairstyle involves pulling half of your hair back while leaving the other half down, combining elegance with ease.
To style, simply gather the top section and secure it with a stylish hair tie or clip.
This look works beautifully with both casual and smart outfits, making it perfect for outings or events.
For added flair, consider incorporating subtle waves in the loose section for a softer look.
36. The Refined Slick Side

The refined slick side hairstyle conveys an air of sophistication and confidence, perfect for formal settings.
This look features hair slicked back to one side with a defined part, maintaining a polished appearance.
To achieve this style, apply a strong-hold gel and comb the hair back, ensuring a neat look.
It pairs well with tailored suits or business attire, projecting professionalism.
To elevate your style, consider adding a pocket square or a classy watch.
37. The Elegant Low Bun

The low bun hairstyle is a classic, elegant choice for sophisticated occasions, keeping hair neatly styled while emphasizing facial features.
This style involves gathering the hair into a low bun at the nape of the neck, creating a polished look.
To create this, simply pull the hair back and secure it with a hair tie, wrapping a small section around the base for added flair.
This hairstyle pairs beautifully with formal wear, offering an air of refinement.
Accessorizing with stylish cufflinks or a classic tie can enhance the overall appearance.
38. The Sharp Edges with Long Top

The sharp edges with a long top hairstyle combines clean lines with length, creating a striking contrast.
This style features a longer top section, sharply contrasted with short sides for a modern look.
To achieve this, consult your barber for sharp trimming on the sides while keeping the top long and texturized.
This hairstyle can be easily styled slicked back or left loose for a more relaxed vibe.
Pair this look with sharp formal attire to showcase your modern elegance.
39. The Fashionable Mullet

Yes, the mullet is back, but this time with a fashionable twist that evokes retro sophistication.
This style features short hair in the front and longer in the back, allowing for a unique and stylish appearance.
To modernize the mullet, consider adding texture and keeping the sides faded for a sleek profile.
This look pairs well with bold outfits, making a statement at any event.
Accessorize with a vintage jacket or unique footwear for a complete standout look.
40. The Vintage Textured Crop

The vintage textured crop brings a modern feel to a classic cut, adding interest and shape.
This hairstyle features shorter sides with a textured top that can be styled in various ways.
To achieve this look, ask your barber for a textured cut on top while keeping the sides neat.
It’s perfect for maintaining a stylish appearance without too much effort, making it ideal for everyday wear.
Pair with casual attire or dress it up with a blazer for a smart, sophisticated look.
41. The Classic Long Hair with Waves

Long hair styled with waves creates an effortlessly sophisticated appearance suitable for many occasions.
This hairstyle emphasizes length and texture, perfect for those looking to make a statement.
To achieve waves, use a curling wand or braids to create a natural wave effect, finishing with a light-hold spray.
This look pairs beautifully with casual outfits or smart wear, making it versatile.
Consider adding a leather jacket for an edgier vibe, or keep it classic with a tailored coat.
42. The Sharp Business Look

The sharp business look features a clean, precise hairstyle that radiates professionalism.
This style is typically short on the sides with a slightly longer top, styled neatly for a polished appearance.
Use a quality gel or pomade to keep the top slicked back, ensuring a well-groomed look.
This style pairs perfectly with business attire, projecting confidence in any professional setting.
Complete the look with a tailored suit and polished shoes for that added touch of elegance.
43. The Dapper Faded Comb Over

The dapper faded comb-over is a stylish and refined look that brings sophistication to any outfit.
This style features a clean fade that transitions into a longer top, allowing for a classic comb-over finish.
To achieve this, style your hair with a lightweight pomade, combing it over to one side for a polished look.
It’s perfect for formal and casual occasions alike, making it a versatile choice for modern gentlemen.
Accessorize with a stylish shirt or tie to enhance the overall dapper appearance.
44. The Timeless Tucked Look

The timeless tucked look is the perfect blend of sophistication and simplicity, emphasizing facial features beautifully.
This style involves tucking the hair behind the ear or back for a clean finish.
To achieve this, ensure your hair is well-groomed, and use a light hold gel to keep it in place.
This hairstyle is extremely versatile, working for both casual outings and formal events.
Pair it with a tailored blazer for a look that’s sure to impress, showcasing your refined sense of style.
Conclusion

These 44 vintage old money hairstyles are more than just trends; they’re a way to express confidence and timeless elegance.
Whether you’re going for a classic side part or an adventurous rockabilly style, there’s something here for everyone.
Embracing these hairstyles can enhance not only your appearance but also your overall style game, allowing you to feel like a million bucks every day.