Classic Men's Haircuts:
A Guide to Timeless Styles

There's a reason certain haircuts keep coming back. The crew cut was popular in the 1950s, nearly disappeared in the 1970s, came back in the 1990s, and is as common today as it's ever been. The side part has been a respectable choice for businessmen since before any of us were born. The taper — that smooth graduation from longer on top to shorter on the sides — is the default setting for men who want to look good without putting too much thought into it.

At City Barbers on the Upper East Side, we've been cutting these styles for over 50 years. The barbers on our team have collectively done more crew cuts, tapers, and Ivy Leagues than we could count. What follows is our guide to the classic men's haircuts — what they are, who they suit, and how to describe what you want when you sit down in the chair.

The Crew Cut

The crew cut is one of the most versatile short haircuts in existence, which is why it has never really gone out of style. At its core, it's a uniformly short cut with a gradual taper on the sides and back, slightly longer on top — typically 1 to 2 inches. The defining characteristic is the flat or slightly rounded top and the clean graduation down the sides.

The crew cut works on almost any face shape and is particularly flattering for men with round or square faces, where the short sides minimize width and the length on top adds height. It's low maintenance, looks good growing out, and requires minimal product — a light matte clay or nothing at all works fine.

When asking for a crew cut at the barbershop, be specific about length: "half inch on top with a taper on the sides" gives your barber something concrete to work with. You can also specify whether you want a natural arc on top or a flat top, which has its own distinct look.

The Taper Cut

The taper is arguably the most universally flattering of all classic men's haircuts. Unlike the fade — which takes the sides down to very short or skin — the taper is a graduated transition that maintains length on the sides, just shorter at the bottom than the top. A standard taper starts at a medium length at the temples and graduates to a shorter length at the neckline.

The beauty of the taper is its versatility. Pair it with a longer top and you have something that works in a professional environment and a Saturday brunch. Keep it shorter overall and it reads as clean and athletic. The taper is forgiving of almost all hair types and works well with both straight and wavy hair.

If you're getting your first haircut at a new barbershop and you're not sure what to ask for, "medium taper, keep the top natural" is a reliable starting point. It's clean enough to look intentional, flexible enough to accommodate your hair's natural movement.

The Side Part

The side part is the quintessential professional haircut. It's what executives wore in the 1950s, what Mad Men characters wore in the early 1960s, and what half the men in any Manhattan office building wear today. The fact that it has survived this long — through the long-hair era, the post-grunge era, the undercut boom — is testament to its fundamental correctness as a men's haircut.

The key to a good side part is execution: the part needs to be clean and straight, the hair on the heavy side needs to lie flat and smooth, and the taper on the sides needs to be tight enough to give the style definition without going too short. Many side parts are ruined by an imprecise part line or by sides that are too long, which causes the hair to lose its shape within a day or two.

When requesting a side part, tell your barber which side you naturally part on (usually you have a natural part — go with it), how much you want the sides tapered, and whether you want the top to be slicked back or forward. Some clients like a harder part, achieved with a comb directly on the scalp; others prefer a softer part that's combed in but not severe. Both are valid choices.

The Ivy League

The Ivy League — also called the Harvard Clip or the Princeton — is a variation on the crew cut with a bit more length on top, enough to comb over to one side. Think of it as the crew cut's more polished cousin: same clean tapering on the sides and back, but with 1.5 to 3 inches on top, giving you the option of styling it forward or to the side.

The Ivy League is an excellent choice for men who want a short cut that can be dressed up or down. Left to air dry, it reads as casual and effortless. Combed with a product, it looks intentional and put-together. It's the kind of haircut that looks appropriate at a board meeting and at a weekend barbecue without requiring a change in styling.

The Classic Taper Fade

The taper fade occupies the middle ground between the traditional barbershop taper and the modern skin fade. Where the classic taper graduates the hair smoothly but doesn't go particularly short, the taper fade takes it down lower — often to a very short length at the temples and neckline — while keeping the top at a wearable length.

The taper fade has become one of the most requested cuts at barbershops like ours over the past decade, and for good reason: it's sharp, it has a high-contrast look that photographs well, and it grows out more gracefully than a full skin fade. The graduation point is lower on the head than in a traditional taper, which gives the style a more contemporary feel while still being firmly rooted in barbershop tradition.

The Buzz Cut

The buzz cut is the most democratic of all men's haircuts. Strip away the styling variables — the part, the length, the taper — and you're left with a single clean number across the whole head. It requires minimal maintenance, costs less than a full haircut in most shops, and looks good on a surprisingly wide range of face shapes and head shapes.

There are variations: the high and tight (very short on the sides, slightly longer on top), the flat top (squared-off top surface, sides faded down), the butch cut (slightly longer uniform length, perhaps a 3 or 4 guard). But all of them share the essential quality of the buzz cut: clarity, simplicity, and a certain kind of confidence that comes from committing to short hair.

The Pompadour

The pompadour is the flashiest of the classic cuts — it asks for more volume, more product, and more maintenance than its companions. At its most restrained (think a medium-length modern pomp with a skin fade), it's entirely suitable for professional environments and reads as stylish without being ostentatious. At its most dramatic, it's a statement that belongs at a rockabilly show.

The modern pompadour is a step back from its 1950s predecessor: shorter overall, with a fade or taper rather than a hard part, and styled with a matte product rather than brilliantine. This version works well for men who want a cut with some personality — something that's clearly not just a "default" haircut — but don't want anything too high-maintenance or attention-seeking.

How to Talk to Your Barber

The most important thing you can do before sitting in the chair is have some vocabulary ready. You don't need to be an expert — that's what your barber is for — but being able to say "medium taper, keep the top at about an inch and a half, natural texture" is more useful than "just short on the sides and longer on top."

Some helpful terms: guard length refers to the clipper attachment number (1 = very short, 4 = medium-short, 8 = medium); taper means a gradual graduation from longer to shorter; fade means a tighter version of a taper, often going quite short or to the skin; texture refers to the natural movement of the hair; disconnect means a sharp contrast between the top length and the sides with no graduation.

If you're not sure what you want, saying so is fine. A good barber — and all four of ours at City Barbers have been doing this for years — will look at your hair texture, face shape, and what you're already working with and make a recommendation. That conversation is part of the service.

The classics are classics for a reason. They've been refined over decades of barbershop practice into shapes that work for human heads, human hair, and human lifestyles. Coming in for a crew cut or a side part is not a failure of imagination — it's the accumulated wisdom of 70 years of men's grooming distilled into something practical and genuinely good.