5 of the Hottest Dapper Haircuts Worn by Celebrities

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Looking to get a new haircut but not sure where to start? Consider a dapper haircut – also known as a gentleman’s hairstyle – over your usual short, easy-to-maintain choice. However, before you find yourself clueless in the barber’s chair, think about the following points – and get some celebrity inspiration.

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man with a dapper haircut and sunglasses

What is a Gentleman’s Haircut?

To put it simply, the gentleman’s haircut has been around for years and is considered a classic option. Yet, no one sits down and says, “Give me a gentleman” without some context. Specifically, a gentleman’s haircut is clean cut yet long enough on top that you can brush or comb it to the side. For some modern context, picture a quiff or undercut.

In more barber-speak, the cut features tapered sides around the temples, clear comb marks, and a short or medium length on top. Updated versions – assuming James Dean isn’t your go-to style inspo – add some fading along the sides and a bit of texture on top. In turn, a gentleman’s cut is ideal for guys with thick, wavy, or curly hair.

Gentleman’s vs. a Regular Haircut

As the antithesis of the gentleman’s haircut, the regular haircut – yes, that’s its name – has less length and less contrast and, in turn, requires less maintenance. It’s also less “dapper” and often looks a bit basic, like you can’t be bothered with learning how to style your hair.

Black and white shot of a man with a dapper haircut

It’s also more commonly given to boys – obviously, for practical reasons – but isn’t unheard of on grown men. A “regular” appears similar to a gentleman’s cut in that it has some hair on top, but there is minimal difference between the sides and top – everything just gradually progresses – and features a defined side part.

For decades, the regular haircut was considered a businessmen’s staple, likely in line with Don Draper-esque gray flannel suits, but its origins, in fact, go back to the Roman Empire. Not to be confused with the Caesar – itself a type of regular men’s haircut – with short hair, accompanied by a cleanshaven face, left very little for the enemy to physically grab onto and prevented the spread of lice.

Beyond the Caesar, regular men’s haircuts encompass crew cuts, buzz cuts, and the Ivy League.

Getting a Dapper Haircut

As a solid starting point, do your research about men’s haircut terminology and present a few pictures reflecting what you’re looking for. For the modern man, that often looks like – or falls in line with – the quiff.

What Do I Tell My Barber for a Quiff?

Man in a suit with a dapper haircut

As we have explained on here, there’s no single quiff style, with contrasts and lengths creating a range of cuts that work with practically all face shapes. In turn, telling your barber you want a quiff isn’t the most effective strategy. Instead, going into your appointment:

  • Provide your barber with a picture. As much experience as he has, a picture always says a thousand words.
  • If you can, grow your hair out ahead of time, so that he has some length to work with.
  • Request that he keep it shorter on the sides and in back and go longer on top. Grade 2 sides are relatively popular, and for a modern dapper look, consider asking for a fade or even a skin fade.
  • In line with the rules concerning a gentleman’s cut, make sure he leaves you with enough to comb over.
  • Think about if you want a side part. While it’s not a true gentleman’s haircut staple, plenty of men ask for this feature. A particularly dapper barber might even go the extra mile and shape it in with a razor.
  • Think about fringe, as it can add texture and body to your quiff.
man with a gray hoodie and a dapper haircut

How Do You Style a Hard Part? 

Unfortunately, styling a hard part isn’t as simple as combing the hair away and out. The line, whether natural or shaved, divides your hard into two distinct sections, leading to an asymmetrical look. Your hair, too, gets styled in opposite directions on both sides, and you’re left dealing with a mix of down-to-the-scalp short hair and longer locks meant to create a quiff.

As you go about this:

  • Regardless of your haircut, make sure the strands of hair fall away from the hard part, with no overlap or frizz. Use a product and then comb it.
  • Don’t think too much about the sides. For a gentleman’s haircut, they should be relatively short, anyway, and often just need to be smoothed out with pomade or a similar product.
  • For quiffs and longer-length styles, comb your hair up and back, but let the sides hold their natural position.

Dapper Hairstyles: Celebrity Inspiration

Justin Timberlake with a dapper haircut

Natural Pompadours with Low Drop Fades

Example: Justin Timberlake

Pompadours are here to stay, and wearing it with a skin fade creates a more modern twist. The great thing about a low-drop or mid-fade is that you can add it to a haircut of any length. Have your stylist cut the top to your desired length and then have the sides and back neat and buzzed just above the ears.

  • A cool spin on this look is tousled waves on top with sharp, clean sides. 
  • Balance out the look with a full but shaped beard.  
Oscar Isaac's layered hairstyle

Layers, ​Layers, and More Layers

Example: Oscar Isaac 

Adding layers to your dapper hair is a huge trend right now – this style is particularly nice for men with salt-and-pepper hair.

Layers add more texture and depth to any hairstyle. With more layers, you are creating a “messier” dapper hairstyle but one that can still achieve a “put together” look.

For work, add a strong hold product for a polished look. To be more casual, use a light hold product to create a tousled look.  

Charlie Heaton with a slicked back hairstyle

Wear Your Hair Slicked Back

Example: Charlie Heaton

A slicked-back hairstyle will never go out of style. To add a little something different to it, use product to create a matte finish and add texture. 

Make sure to keep your neckline clean and trimmed to keep the look as tidy as possible.

Add some freshness with a side part. Slick the hair back and toward the sides while keeping some the front tendril dangling near your eyes.  

Kit Harington with Medium-Length hair and a Loose Side Part

Medium-Length with a Loose Side Part 

Example: Kit Harington

Make it look effortless! Get this classic cut, and then shake it up with a bit of styling mousse. If you loosely part it on the side, some strands may fall the other direction or go straight backward.

That’s okay—the mousse will keep you looking put together, but you won’t appear to have spent hours in the mirror perfecting your image. And you won’t have to! Roll out of bed—your routine will only take about two minutes, et voilà—another dapper hairstyle. 

This dapper look is especially great for second-day hair (we won’t tell – plus the oil is actually good for your hair). Add some dry shampoo for volume and style. 

Nick Jones with the classic buzz cut

The Classic Buzz Cut

Example: Nick Jones

Simple? Yes. Classic? Yes. The Buzz Cut is one of our go-to, no-frills dapper hairstyles. If you’re looking for little to zero maintenance in the morning, this cut is for you.

Just make sure you’re ready to get your haircut every 2 to 3 weeks to keep the length short and neckline fresh. 


Hot Celebrity Haircuts

Lauren Rachel, Men’s Grooming Expert at Boardroom. Since 2004, Boardroom has been the place where men get ready. Boardroom delivers the ultimate relaxed grooming experience for men by providing exceptional haircuts, shaves, and spa services in an elegant, country club environment. Boardroom currently has 27 locations throughout Texas, Tennessee, Oklahoma and Georgia. For more information, visit boardroomsalon.com or facebook.com/theboardroomsalon

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