20 Stylish Men’s Hipster Haircuts

Hipster Haircuts

They involve a variety of styles, mainly haircuts from the 1920’s-1950s with a modern twist. You’ll find some cool classic undercuts, sleeked back hairstyles, pompadours, fades, side parts, full beards, handlebar moustache, and more in the gallery below.

1: Evolved Caesar Haircut

Suitable men’s’ haircuts are sometimes a challenge to modernize, but this one does a great job! Keep the back very short, with the top at least an inch or two long. Comb forward, and create a slightly rounded bang line that is accented by short fade above the ears. 

2: Duck Tail Pompadour

Searching for modern versions of hipster hairstyles is actually simple. Implementation? Better leave it to the pros. This one takes some perfecting, so don’t be discouraged!

3: The New Classic Man Bun

This male hairstyle was seen thousands of years ago amongst tribes and warriors. There were many reasons to leave a topknot growing, honor being one and culture being another. Keep a tight fade all the way around, allowing enough length up top to pull into a small knot or bun. 

4: Pompadour with Faded Sides (and ‘Stache!)

The epitome of the hipster moustache is, in fact, the handlebar. Reserved once for men who wanted to stand out in their class, it has now been adopted by many cultures. Worn with a traditional pompadour, it creates a timeless look. And a nose ring adds just the perfect 21st century accent too!

5: Curly Top and Tight Sides

If you want all out lazy hipster hair, look no further than this style here. The back and sides are almost gone, leaving a pile of messy curls that can be brushed forward, sleeked back or tousled and left alone! 

6: The Big Wave

Searching the next perfect artistic look for guys? Need to update your repertoire but have no clue what to do? Start growing hair up top for an amazing super tall pompadour! You can still keep the sides neat and short with a fade or undercut.

7: The Intellectual

A hipster beard doesn’t have to be long to be trendy. This stubble defines the jawline well, and the combed over wave on top is truly epic! Get your thinking cap ready because some long conversations are coming your way! 

8: The Colin

Mainstream media has influenced the newly popular hipster haircuts more than any other source. Think about the style influence celebrities have today! This look, which is fairly simple, creates the height and volume while showing off the good bone structure. Wear with dignity!

9: Curly-Q Dan

This cool and funky style offers the idea of men’s sleek vintage hairstyles with a modern quirk. Pair with sideburns, style with a strong hold product and wear any time for the pure “WOW- factor!”

10: Silver Blonde Undercut

Ash blonde and silver blonde hair has made a splash in hair color trends. Now it’s a color for the young, guys and girls. Pair with your favorite undercut haircut and wear with a tousled top.

11: Fade with a Wavy Top

A hipster haircut should be trendy and with a twist, but also take into account your hair texture. If you have naturally wavy hair, this fade is a great idea. Styling those smart flicks won’t be a problem with a good texturizer.

12: Asymmetrical Side Part

This boy knows what he wants, and it’s picture-perfect hair! The over-the-top bronze highlights, accurate side part and asymmetry make a sophisticated hairstyle for those who don’t want just a plain hairstyle. 

13: Choppy Side Part for Thick Hair

This short version of the pompadour blends with a chiseled fade. It’s a distinguished look we think deserves to live on in the history books! Styled with wax or glue, this look is not going to budge any time soon. Trust us! 

14: Fade for Wavy Hair

When you want a hipster haircut, but you have a day job, look no further than this incognito look. There are clean lines, the faded bottom edge, and perfect tapering of length. Neat, flattering and individual. 

15: Creatively Styled Long Top Short Sides

Here’s a cute idea on how to style a long top short sides haircut for guys. Parting the long section in the middle at the back of the head is not a big deal, but that’s a new thing to see. Go ahead, get creative!

15: Creatively Styled Long Top Short Sides

Here’s a cute idea on how to style a long top short sides haircut for guys. Parting the long section in the middle at the back of the head is not a big deal, but that’s a new thing to see. Go ahead, get creative!

16: Pompadour With A Twist

A male version of what almost resembles your Grandma’s updo, this pompadour has a life of its own… and likes to party! The cut features a tapered fade all the way around, giving centre stage to the long loose curls effortlessly swept up and back. 

17: Highlighted Pompadour

The concept of this hipster hairstyle is the play of contrasts – dark and blonde hair, shaved temple areas and sideburns that suddenly stop to point to the lips. Such styles are anything but hackneyed, so they can give you a great deal of new confidence…and height! 

18: Casual and Free Hipster Style

This is the ultimate hipster look for guys. And it’s effortless! You can literally wake up, comb your hair with your fingers, and POOF! It’s a strong look combined with a well-groomed beard, which creates an interesting contrast. Wear with anything! You’ll always look like you’ve just got out of bed, in a chic and cool kind of way. 

19: Hi-Cut V Fade (with Curls!)

This look is a fun crossover between straight and curly. Plus, there’s a fresh idea of an undercut along the sides that blends into the V-cut nape. This style certainly looks more impressive if your hair is black or dark brown. 

20: The All-Star Player Full Hawk

Another popular hipster hair cut started as a much different style many years ago in tribal cultures. Nowadays every subculture adopts it and dresses it up in a more or less unique way. This look is fairly hipster-esque.