The Definitive All-Season Haircut Guide

Illustrations by Lee Caces
Graphics by Gene Exaltacion

A truly good look is timeless. There’s something to be said for trends, but when it comes to hairstyles, that shouldn’t preclude the classic, the practical, and the versatile. Here are some handsome hairstyles that are suitable for any occasion.

1. Tapered Buzz Cut

Buzz Cut IG

Following the fleeting fixation with long hairstyles like the top knot and the man bun, men are once again opting for very short hairstyles. The shortest, of course, is the buzz cut–timeless, practical, simple. Put a modern spin on it by keeping it very slightly longer on top, and have it taper all around for a smooth, even fade.

As seen on Brad Pitt, Drake, Derek Ramsay


Tell your barber to shave your head, using number two clippers for the top, and gradually fading down to zero on the sides and back. Then have it cleaned up and detailed with a razor.

Maintain it by visiting the barber a little more often to keep it clean and even. Apart from that, this style really doesn’t need much maintenance at all.


2. High & Tight

High & Tight Left Web

Consider this the modern, more refined version of the faux hawk–great for men who are after the practicality of a short hairstyle, but don’t have the shapely noggin for a buzz cut. It can do a lot to make an older man look young, and a young man look sportier.

As seen on Ryan Reynolds, Zayn Malik, Tony Labrusca


Tell your barber to take a clipper to the sides and back, leaving it longer on top with a little extra length in front. Fading the sides will also keep this from looking too much like a standard crew cut.

Maintain it by moderating your use of product. This is the kind of hairstyle that works well with just as little pomade for a neat look, or without any at all for a laid back look.


3. Classic Side Part

Classic Side Part IG

This is your standard medium-length hairstyle–easy to wear, easy to style, and appropriate for the office and the weekend. It’s also the kind of cut to keep for the long-haul– a timeless and versatile look you can ask your barber for again and again without it ever going out of style.

As seen on George Clooney, Justin Timberlake, Ian Veneracion

side part

Tell your barber to give you a scissor cut, keeping it textured on top, and shorter and layered on the sides.

Maintain it by moderating the shampoo. This kind of hairstyle doesn’t work if your hair is too dry, so be frugal with your shampoo. Thrice a week or every other day should be enough, depending on how much product you use. You can also opt to use dry shampoo on the days you’re not washing your hair.


4. Old School Wave

Old School Wave

This one comes straight out of the 1920s–the clean, coiffed, distinguished look that you might know best fro Baz Luhrmann’s The Great Gatsby. It’s a medium-length hairstyle, slicked back at an angle, and it works to add a little retro flourish to your look while keeping with the times.

As seen on Leonardo DiCaprio, Benedict Cumberbatch, Jericho Rosales


Tell your barber to keep it long and layered–that’s the key. Then have him taper down the sides, still keeping them at medium length. Make sure he refrains from using clippers for this haircut–your barber should just stick to scissors and shears.

Maintain it by letting it rest as often as possible. It’s a relatively long and full hairstyle that tends to involve using a lot of product. Make it a point to wash and rinse regularly.


5. Messy Pompadour

Pomp Left Web

One of the options that works well for men with curly hair or straight but thick hair is to keep it long and thick in the front and short everywhere else, simulating a very casual pompadour when brushed up and combed well. This can also be styled as a more disheveled, creative-class look by using a matte-finish styling product.

As seen on James Franco, Bruno Mars, James Reid


Tell your barber to leave as much volume, length, and texture in the front, tapering towards the back, and keeping it short with scissors on the sides.

Maintain it by using a blow dryer occasionally. It will help you maintain the brushed-up volume in front. Too much warm air could damage your mane, though, so it’s best to also use conditioner at the mid to ends of your hair strands after you shampoo.


6. Long & Layered

Long & Layered Left Web

It takes a lot of courage (not to mention the right kind of hair) to try and pull off a long hairstyle. If your hair is naturally curly or wavy and of the right thickness and volume, long hair might just work to add character to your look. Just make sure you’re ready for the maintenance!

As seen on Kit Harrington, Adam Driver, Luke Landrigan


Tell your barber to keep the baseline low–up to your shoulders if your hair is long enough–and the layers long, so there’s enough weight for everything to fall properly.

Maintain it by using conditioner after you shampoo to prevent your hair from drying. You’ll also need to visit your barber at least every 2 months to trim any awkward cowlicks, and to maintain your mane’s shape.


Let your barber know which cut you’d like to try. Book your next barbershop appointment at your preferred Felipe and Sons branch here.


This article originally appeared in Compass: A Style Premier for the Modern Man, November 2016 with minor edits by the Felipe and Sons team

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