Hipster Haircuts: 9 Looks That Breathe New Life Into Your Style

Ever since James Dean first graced the silver screen in the early 1950s, it became immediately apparent that while clothes don’t make the man, a sharp haircut just might. Today’s hipster haircuts are heavily steeped in vintage nostalgia, but with a fashionable and decidedly modern twist.

From classic tapers and pompadours to more far-out styles like cropped fringe styles and dramatic undercuts, this season’s hipster haircuts are a sure way for you to turn heads this year.

Read on as we dig into the most iconic hipster styles of 2019.

Nine of the Coolest Hipster Approved Cuts Around

From hard parts to clipper cuts and everything in between, here are this season’s hottest haircuts.

High Fade with a Hard Part

One of the most meticulous styles on our list, the high fade is one of the best looking and most clean cuts on our list. This haircut starts with a high skin fade that gets slightly longer towards the crown of the head.

The hair on top is choppy and relatively short, but still long enough for a combover. To elevate this style even further, ask your barber for a hard part - a line that’s razored into your part to create a more dramatic style.

To style this cut, add some matte finish pomade or clay to your dry or slightly damp hair, distribute it throughout the top of your hair, and comb to the opposite side of your hard part. This decidedly 21st-century look is popular with metropolitan hipsters from New York to Seattle.

Tapered Sides with a Brush-Up

This tapered cut is similar in many ways to the high fade cut we’ve described above. However, instead of a high and tight fade, the sides are tapered with scissors. This leaves more length at the sides without looking messy or unkempt.

The top is left fairly long and textured heavily. When it’s time to style this cut, add a bit of matte pomade or clay to dry or damp hair, and blowdry as you brush your hair up. The resulting style is edgy and rock ‘n roll, without losing any of it the cool hipster vibes you’re after.

Slick Back with a Beard

The classic slick back is a timeless style that’s been en vogue with men everywhere for well over a century. The addition of a full beard helps break up some of the stuffiness of this cut and shows other people that you’re serious about your look, but you don’t take yourself too seriously.

The slick back is ideal for guys who like to wear their hair longer on the sides. To achieve this style, ask your stylist for a slick back scissor cut, and sit back while they work their magic. To style this cut, reach for some high shine water-based pomade and apply it to slightly wet hair. Run a comb through your mane, and you’re good to go!

Smooth Viking Pomade

smooth viking pomade for men

A water-based hair styling that gives any hair type the fine boost it needs to achieve a sleek look. With our pomade for men, you can keep your hair in place all day long, thanks to its long-lasting control effect.

Dry Slick Back

Similar in composition to the classic slick-back, this cut is less formal and easy to style, so it’s perfect for guys who don’t have a ton of time to do their hair in the morning.

Ask your stylist for a slick back scissor cut, but let them know you’ll be wearing the style dry and messy. They’ll add some texture to help break up the stuffiness of the classic slick back while giving your hair more life and volume.

Styling this cut is easy, too. Apply some matte pomade or fiber cream to dry or slightly damp hair, and mess it up as you blowdry. Throughout the day, if your style needs a refresher, just run your hands through your head, and you’ll be back to looking like the unaffected rockstar you are faster than you can say “Ok Computer is my favorite Radiohead album.”

Side Swept Fringe with a Fade

This side swept style is a play on other well-worn hipster classics, like the pompadour and tapered scissor cut. This cut employs a fade on the sides with a textured top that’s a bit on the longer side, which helps you create a more dramatic style.

For this cut, you can opt for a low, medium, or high skin fade on the sides. For the top, leave a little extra length, and have your stylist add plenty of texture. Styling this cut is especially easy; add some matte pomade or fiber putty to your slightly damp hair, and style it with your hands. The whole styling process should take you less than a minute.

The V-Neck

V-shaped neckline like this image from Haircut Inspiration is a stylistic choice that can be added to virtually any of the styles on our list. Instead of a standard fade, have your stylist fade your hair in a V shape, with the back a bit longer than the sides.

This vintage style is especially popular among vintage enthusiasts and anyone who is enamored with the culture of the past. If you’ve ever marveled at how cool the guys on Boardwalk Empire or Peaky Blinders look, the V-neck may be an excellent choice for your next style.

Styling this cut will vary depending on what you have going on up top. V-neck styles tend to look best with a pompadour, or a slick back, and it can be an especially striking style for anyone who has wavy hair.

The Undercut

Undercuts have become the “it” haircut of the last year or so, but this disjointed style is nothing new for hipsters, who have been sporting versions of the undercut for years.

Unlike a standard haircut, which blends the shorter sides of the cut into the longer top, an undercut leaves the top and sides disjointed. This creates an abrupt transition between the top and the sides. It creates a dramatic look that lends itself well to many different styles.

There are several popular ways to style this cut. Leaving the top long and slicking it back is one of the most popular ways to wear an undercut. A pompadour is another popular way to style this cut, with a pronounced “poof” of hair at the front of the head.

Basically, there’s no wrong way to style an undercut, and they work well with any of the top styles on our list. For your undercut to look it’s best, ask your stylist to buzz the sides to one length, or get a skin fade. For the most dramatic (and best looking) results, ask for a #2 or #3 on the sides.

The Man Bun

Say what you will about this much-maligned style, but the man bun is here to stay. While many hipsters deride this style and look at it as a cheap derivative of hipster culture, it looks great on virtually everyone.

Styling a man bun is incredibly easy. All you’ll need to do is grow your hair out and put it in a bun. Depending on how clean-cut you’d like your look to be, there's multiple ways to style it. You can buzz the sides, taper them with scissors, or leave them the same length as the rest of your hair.

If you leave the sides long, make sure you regularly get the back of your neck cleaned up to avoid looking like a caveman. You can do this yourself if you have a three-mirror set up in your bathroom. Or, any stylist can clean you up in 30 seconds for just a few bucks.

The Pompadour

One of the most well worn and historical styles of all time, the pompadour derives its namesake

From Madame Pompadour, a mistress to an 18th-century French king. Her style was an exaggerated updo with a pronounced quaff at the front of her head.

It wasn’t until the 1950s that men everywhere began adopting this stylish cut. This is because it's popularity began with icons like Elvis, James Dean, and Little Richard. While it’s fallen out of fashion recently, the pompadour has always been popular with rockers, punks, and hipsters. As a result, it’s a great style to start with if you’re looking for a hipster-approved hairdo.

pompadour can be applied to many different styles, but it usually looks best with cropped sides and a relatively long top. Depending on how dramatic you’d like your style to be, you can adjust the length of the top. Pompadours are appropriate for any situation, while longer ones may be a bit too rock ‘n roll for the office.

Traditionally, styling a pompadour requires a strong-hold pomade, circular brush, and blow dryer.

Conair Hair Styling Dryer

conair styling hair dryer

This 3 in 1 Styling System features three attachments to achieve the perfect look for all hair types; Features 2 heat/speed settings and a cool shot button to lock styles into place.

But, you can achieve similar results by styling your pompadour wet and then allowing it to dry. There’s no shortage of resources online that will guide you when it comes to styling this iconic haircut.


uppercut deluxe quiff roller hairbrush

 A high quality, small, round brush with ball tipped bristles designed to add life and volume. Perfectly sized and wall tipped bristles spaced for air circulation prevent pulling. Rubber non-slip grip for easier glide and better control.

Final Word

From pumped up pompadours to disheveled undercuts, hipster hairstyles are enjoying a moment in the sun right now. The cuts on our list above represent the most popular hipster haircuts of the day. With these options above, you’ll have no problem channeling an effortless and unbothered look.

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