4 Classic Men's Haircuts That Never Go Out of Style (and How to Rock Them Today)

When it comes to men's grooming, some styles simply stand the test of time. While fashion may change, certain men's haircuts remain perpetually cool, reliable, and versatile. Whether you're heading to a job interview, a first date, or just want to feel confident every day, a classic haircut is your secret weapon. In this post, we'll uncover four timeless men’s hairstyles, explore why these cuts endure, and reveal how you can make them your own with a modern touch.

Why Classic Cuts Endure

Classic men's haircuts have remained popular for decades for good reason — they flatter most face shapes, are easy to maintain, and adapt beautifully to your unique style. From neat side parts to rugged fades, these hairstyles serve as a strong foundation for personal expression. Plus, they never look dated in photos (meaning, no future haircut regrets!). Let’s dive into the big four:

1. The Timeless Side Part

History & Enduring Appeal

The side part is synonymous with sophistication and easy style. Having graced the heads of Hollywood icons like Cary Grant and modern stars like Ryan Gosling, this haircut has proven it's here to stay. Its main allure lies in its clean lines and adaptability—it looks just as good with a sharp suit as it does paired with jeans and a tee.

How to Rock the Side Part Today

Ask your barber for: Clean, tapered sides and longer length on top (about 2–4 inches). The part should be clear but not overly harsh.
Styling tips: Use a comb to create a crisp part. A light pomade or styling cream keeps it neat with a natural finish. For a modern twist, add just a touch of textured messiness on top.
Who it suits best: Just about anyone. Particularly helpful for guys with wavy or straight hair, and fits most face shapes.

2. The Undercut

History & Enduring Appeal

The undercut dates back to the early 1900s and made its biggest comeback in the 2010s, seen on everyone from David Beckham to Brad Pitt. Its defining feature is the sharp contrast between shaved or closely cropped sides and a longer top—bold, unmistakable, and remarkably versatile.

How to Rock the Undercut Today

Ask your barber for: Very short sides (even a fade) with noticeable length left up top. You can go slicked back for a classic feel, or embrace a more textured look for modern flavor.
Styling tips: Matte clays and light gels work wonders for adding volume and texture. For a bold statement, slick hair straight back, or use a matte paste for a looser, more casual finish.
Who it suits best: Ideal for men with straight or wavy hair. The contrast works well for most head shapes, especially if you want to elongate rounder faces.

3. The Crew Cut

History & Enduring Appeal

Popularized by military and Ivy League students, the crew cut's fuss-free, athletic look has never gone out of fashion. It’s the ultimate low-maintenance style that still looks sharp and professional.

How to Rock the Crew Cut Today

Ask your barber for: Short back and sides (usually 0.5 to 1 inch) that blend into a slightly longer top—nothing too extreme. The key is the gradual taper.
Styling tips: For most, this cut requires minimal effort—a little dab of lightweight product helps control any stray hairs. Jazz it up by asking for a bit more length on top for added texture, or combine with a fade for a modern twist.
Who it suits best: Just about everyone, especially men with active lifestyles or those who prefer no-fuss, smart looks.

4. The Classic Pompadour

History & Enduring Appeal

Immortalized by Elvis Presley and reinvented by modern celebrities like Bruno Mars and Zayn Malik, the pompadour is all about high volume and irresistible style. Its defining feature is the voluminous, swept-back top, which delivers an unmistakable retro-meets-modern effect.

How to Rock the Pompadour Today

Ask your barber for: Short back and sides (a fade or undercut works well) with plenty of length left on top to give you lift.
Styling tips: Towel dry hair, add a volumizing mousse or pomade, and blow-dry upwards while brushing back. A round brush helps in sculpting that signature wave. For a relaxed version, leave the top messier and avoid over-slicking.
Who it suits best: Great for men with thick hair; works wonders for elongating round or square faces.

How to Choose the Right Classic Cut for You

When selecting a classic haircut, consider your face shape, hair type, and lifestyle. Talk to your barber about your daily styling habits and how much maintenance you’re comfortable with. Remember, classic doesn’t have to mean boring—any of these styles can be modernized with fades, texture, or subtle color.

Oval faces: Can rock most styles, so feel free to experiment.
Round faces: Try styles with volume on top (like the pompadour or undercut) to elongate your face.
Square faces: Soften the look with styles that are textured and have some movement, like a modern side part or loose pompadour.
Long faces: Wear styles with less height and more balanced proportions, like a crew cut or classic side part.

Products matter, too. Invest in quality pomades, matte clays, or lightweight styling creams depending on the finish you prefer. And don’t skip regular barber visits to keep your shape sharp!

Conclusion: Old-School Cool, Modern Edge

There’s a reason these classic men’s haircuts have endured for generations—they’re flattering, adaptable, and always in vogue. Whether you favor the timeless elegance of a side part, the bold confidence of an undercut, the get-up-and-go energy of a crew cut, or the statement style of a pompadour, there’s a look that’ll serve you all year round. Next time you visit your barbershop, ask your stylist about these cuts and how they can make the look work for your hair texture and face shape.

Remember, a great haircut is more than a style—it’s confidence, charisma, and a touch of personality, all rolled into one. Choose your classic, make it your own, and step out looking (and feeling) your absolute best!

Ready for a Classic Transformation?

Discover more about classic and modern men's haircuts, grooming tips, and barbershop secrets right here on our blog. Looking for inspiration? Browse our gallery or book your next appointment with our expert stylists today!