The ultimate gallery of medium haircuts for men: 2021

Not too long, not too short, but just right. If Goldilocks had ended up in a barbershop instead of a bear house, we can say with some confidence that she would have opted for a medium length haircut.

A mid-length cut, which occupies that sweet spot between long and flowing and short and conservative, gives a bit of rock ‘n’ roll flair without routinely being mistaken for a woman from behind. And now is the perfect time to take the plunge. Mid-length styles have found their way into the minds of some of the world’s greatest tonsorial trendsetters, further cementing their already significant style credentials.

But where to start? For many of us who grew up with short back-and-side cuts, the medium-length thing is new territory. What are the main styles? How should you style them? And how can you transfer the image in your head to the person who is hovering over it with scissors?

To answer all of the above and more, we’ve gathered everything you need to know about medium length hairstyles in one convenient place. Browse the tips and our well-stocked gallery to point you and your hairdresser in the right direction.

Key terms for medium hair

Let’s get the hairdressing jargon straight first. Understanding these terms will help you narrow down what you actually want. Plus, less guesswork for the hairdresser is usually a good thing.

jerky

When your stylist cuts sections of hair in a defined but uneven or asymmetrical pattern, it is called “choppy.” It is a technique mainly used in medium to longer hairstyles and is used to create depth and texture.

Messy

This one needs less translation. A messy cut is styled to look rough, tousled or just a little unkempt. Bed hair, beach hair… whatever you call it, it’s a popular way to wear medium-length locks. You could say it’s perfectly imperfect: a good way to add character to an otherwise simple cut.

tapered

The taper is a hairdressing technique most commonly used on medium length hairstyles, where two different lengths of hair are mixed together using clippers, scissors, or a combination of both. It results in a smooth gradation between long and short with the back and sides flowing into the hair on top.

Fade

Like a taper, but shorter and fitted with clippers at different incline settings. It is more common with shorter haircuts, but also adds some drama to medium length cuts. Especially if there is an undercut.

Taper fade

Pretty clear. A taper fade is a combination of a taper and a fade that mixes the very short hair at the back and sides of the head with much longer hair on top without looking loose.

undercut

The undercut has been around for decades, but it’s also one of the standout hair trends of the past 10 years. It involves cutting the back and sides short, while keeping the hair on top of the head much longer. It is often combined with a taper, but can also be worn separately. Speaking of which…

Detach

When a haircut is called ‘disconnected’, it means that there are two different lengths of hair that are not mixed together in any way. Short at the back and sides, long at the top and no tapering or fading for graduation between the two.

Choosing a medium length haircut for your face shape

Not every face fits a man bob. A medium length haircut can make one person look like the king of the north and another like his jester. To make sure you finish first, take a long, deep look in the mirror. Because your face shape is key.

Long face and big forehead? No problem. Avoid styles where the hair is brushed up and away from the face and opt for a textured haircut with bangs instead. Leaving out the added height will flatter your features, putting everything in better proportion.

The opposite is true for very round faces. Raised cuts with a length on top, such as tassels and messy, tied up hairstyles help to balance out a round face by adding height. For bonus points, keep things short and tidy and the sides.

Anyone with a heart-shaped face should avoid anything that draws too much attention to the forehead. Go for loose, messy styles instead of pompadours and tufts.

As always, those blessed with an oval-shaped face will suit pretty much anything the barber can throw at them, reasonably.

Top Medium Hairstyle Trends

Mess is the best

Wavy, messy, medium-length locks are in, especially since Timothée Chalamet does it. The look is all about volume and texture and works best with thick head of hair. You can fake it with a blow dryer and lots of sea salt spray, but for best results ask your hairdresser how far you can go.

keep it loose

In the world of short haircuts, the military-rooted high and clean cut has had a bit of a moment, with king of hair trends David Beckham jumping on it. However, medium-length hair is all about low and loose. Loose curls, loose quiffs, loose locks that hang casually over the forehead a la Alex Turner – whatever shape it takes, it’s always painfully cool and it takes some length to make it work.

out of your face

Wearing the hair on and off the face is one of the best ways to style medium length hair. Think classic cuts like the pompadour, the quiff and the smooth back. But be wary: As mentioned, if you’re constantly finding yourself rejecting friends’ why-the-long-face jokes, the extra loft these types of styles bring to the table probably won’t do you any favors.

Mid-Century Madness

Menswear may have had a 1990s revival in recent years, but when it comes to hair, it’s all about the 1950s. From super-tight fades with polished side parts to lazy brushed backs, these throwback cuts dominate barbershop chatter. No wonder: they’re stylish, timeless and bursting with rock ‘n’ roll attitude.

Maintenance & Styling

Getting a mid-length cut to look its best requires a lot of homework, but it all starts in the barber chair. Get some tips and advice from the professional who cuts your hair on how best to maintain your style. They will give you specific advice based on your hair type and the style you have chosen. In general, though, you’ll need a vented brush, a good hair dryer, pomade or wax (depending on the finish you want), some sea salt spray, and a comb.

It is also important to visit the hairdresser regularly to keep things under control. This way, you just need to do a quick trim and clean up every time, rather than having to do the whole thing all over again after a few months of growth.

Main medium haircuts for men

Pompadour

The Elvis. An icon from the 1950s and a stone-cold classic ever since. The pompadour is a timeless medium length hairstyle with some serious loft. Traditionally, long hair on top of the head is brushed forward and back to create a large back-facing quiff. The sides are slightly shorter and brushed back behind the ears to a point at the back of your neck. For a modern twist, wear it with a fade or an undercut instead.

loose crest

Similar in style to the pompadour, the loose quiff is another medium length hairstyle with bangs that are swept up and away from the forehead. The main difference is in the length at the top and the fact that the crest is looser and often falls sideways. The hair should be longer on the top than the back and sides so that the front can be pushed away from the face and styled loosely to the side. The back and sides are tapered, faded or shaved and worn unbuttoned.

wavy mop

Popularized by the likes of Timothée Chalamet and Dev Patel, the wave mop is a relaxed, stylish cut that focuses on texture, volume and length. Not too long, not too short, it is a good example of Goldilocks territory inhabiting a good medium trim. It goes best with thick, wavy hair, but if yours is thinning, sea salt spray is your friend.

Natural medium length Afro

Sure, you can go the ultra-manicured route, but sometimes keeping things natural is the best choice. Just look to people like Donald Glover for proof of that. This style shows off your natural hair while keeping the back and sides in check with a slight taper. For best results, always visit a hairdresser who specializes in Afro hair. Style it in place with a touch of pomade and a good blow dryer.

Smooth back

The classic smooth back is the villain of the medium hair world. When you see someone starring in a movie, you know right away that they’re the bad guy, and yet there’s something we like. Think of it as a low-profile pompadour. The hair is long and styled back in much the same way, but instead flat on the head. Wear it long on the sides or bring it up to date with an undercut or disconnect.

Braids

Braids have been an evergreen trend in recent years, and the style actually dates back centuries in a number of cultures. More recently, Travis Scott, A$AP Rocky and Lewis Hamilton have been among those who have revived the style. Wear them loose, messy or close to the head with cornrows or a unique pattern that your stylist can style.

side part

A classic side part with a short back and sides is certainly timeless, but there is also something stuffy about it. Wearing it loose and relaxed keeps the style vibrant and up-to-date for the 21st century. The hair should be elongated at the top and loosely combed into a side part with your fingers to finish it off. At the back and sides, a tapered leg is the obvious choice for mid-lengths, but a fade can add a contemporary edge.

Straight and layered

For fine, straight hair, this is the perfect choice. At nearly shoulder length, this John Wick-approved style is definitely on the longer end of the medium-length hair spectrum, but it’s low-maintenance. The hair is worn in a loose center part and can either hang straight down or tucked behind the ears. Add layers for depth and texture while keeping styling products to a minimum.

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