Men’s Hairstyles 2021: The Chicago Man’s Top 10 Looks

10 Most Popular Men’s Hairstyles from the Windy City

Chicago is often surreptitiously omitted from men’s fashion publications. Perhaps it’s the harsh weather or the city’s working-class reputation, but fashion fans in New York, London, and Paris are often surprised at the way Chicago men deftly use their hairstyle to display their unique personalities. From fades and undercuts to mid-length comb-overs and pompadours, the following 10 Chicago Men’s hairstyles for 2021 will give you plenty of choices for this year and beyond. For advice for how to care for your hair check out Tips for Men’s Hair Care in Winter.

Men’s Hairstyles 2021: Popular Short Length Styles

Continuing from last year’s exploration of bolder, shorter cuts and hairstyles, this year offers some of the best men’s looks we’ve seen on the streets of Chicago.

Crew Cut

At the top of our list is a timeless men’s hairstyle that never falls out of style – the Crew Cut. With a particular division of length that moves from the hair’s top to the bottom, any wearer of this hairstyle will feel comfortable while looking clean and fresh.

Men's Hairstyles 2021: Crew Cut

Similar to the Buzz Cut, the Crew Cut is easy to wear, easy to maintain, and pairs well with a wide variety of faces. You can also pair your crew cut with faded sides or opt for the slightly longer Ivy League version.


Trending and timeless, the undercut is incredibly popular this year with the men of Chicago. Its high contrast structure is unique and memorable, and it gives the wearer a distinctive, yet refined look. There are many variations on the undercut hairstyle, but they all go hand- in- hand with current men’s fashion. Unlike some haircuts, the undercut is easily recognized at a glance.

Men's Hairstyles 2021: Under Cut

For those looking for a short haircut with a large impact, the disconnected undercut is a fantastic choice. This stylish and eye-catching look features shaved sides with a longer length on top. It also looks great paired with beards, and mustaches.


If you’re not into the sudden changes of the Undercut, then consider fading into one of this year’s most popular men’s hairstyles, the Fade. The best thing about fade haircuts is that they are easily tailored to suit your tastes.

Men's Hairstyles 2021: Fade

If you want a look that’s understated yet stylish, the low fade is an excellent choice. If you’re looking for a more traditional look, the medium fade’s transition from long to short around the temples will leave you looking smart and stylish.

Don’t forget about the High Fade. Featuring sides that quickly taper from long to short, the high fade is a striking and stylish look. The height of the fade isn’t the only option for this hairstyle. Keeping the crossfade low, will create a defined demarcation at the point where your beard starts and the fade ends.

Men’s Hairstyles 2021: Popular Medium Length Hairstyles

If you like the look of long hair but want something that also works well for the office, then these popular medium-length hairstyles for men offer you the most options.


The word “comb-over” brings to mind a balding man in denial, but you don’t have to be balding to enjoy the benefits of one of the most stylish and timeless haircuts for men. Perfect for medium length locks, this asymmetrical style is highly flattering and seriously sophisticated.

Men's Hairstyles 2021: Comb Over

From a neat slick back to a curly brush-over, the comb-over is a versatile, contemporary hairstyle reinvented for the modern gentleman. The comb-over is also a natural look for a bearded gentleman looking for a style that is at once trendy and timeless.


If you like the Undercut look, and don’t mind the use of pomade, the Pompadour is a stylish men’s haircut that’s growing in popularity among the men of Chicago. A regular sight in the trendy neighborhoods of Wicker Park and Logan Square, the Pompadour is the ultimate classic contemporary hairstyle for men in 2021.

Men's Hairstyles 2021: Pompadour

Shaved on the sides with volume on top, the Pompadour exaggerates each of the cut’s components to construct a look that is striking and edgy. The angles of this haircut are more defined. As such, this style is particularly well-suited to those with round faces.


Though the Pompadour and the Undercut have long caught our attention, now it’s time for the Blowout to reign supreme. A latecomer to Chicago, the Blowout is one of the latest trends to hit men’s hairstyles.

Men's Hairstyles 2021: Blowout

The Blowout made its way to Chicago via New York and Paris, where gents have been rocking this sophisticated look for years. This eye-catching style is fashion-forward, and promises to make you look like a style-savvy gust of wind just hit you in the face, which might just happen in the Windy City.

Men’s Hairstyles 2021:  Popular Long Length Hairstyles

Believe it or not, long men’s hairstyles are simple to keep and easy to style. Despite being incredibly low-maintenance, these long hairstyles for men are seriously fashionable, yet relaxed and rugged like a viking in a suit.

Loose Waves or Curls

When it comes to long hairstyles for men in 2021, few cuts can match loose waves or curls. If you have thick curls this hair type can be unruly and hard to tame, but that doesn’t mean you shouldn’t try. Like John Snow, or Jason Momoa, you can turn your curly hair into a rugged source of power that pairs naturally with a wide range of styles, face shapes, and beards.

Men's Hairstyles 2021: Loose Wave Curls

Man Bun

Don’t let the haters get you down. The Man Bun is a timeless classic and a trendy long hairstyle for the men of Chicago. Despite those who said it was just a fad, the Man Bun continuously proves its staying power, and looks set to maintain its popularity throughout 2021 and beyond.

Men's Hairstyles 2021: Man Bun

Half Up

If you’re already a pro at the Man Bun, and you’re looking for a way to change it up, you can always try the Half Up. This style features the top half of hair tied up to achieve a look that keeps your hair out of your face while showing off its length.

Men's Hairstyles 2021: Half Up

Where to Get the Best Men’s Haircuts in Chicago 2021

Shining through the wind and weather, the men of Chicago know how to show off their unique character and represent the finest in grooming, style and fashion. Much like the Windy City itself, they never sacrifice style or concede their appearance to the cold.

If you want to look your best no matter the time of year, drop by Goodman’s Barber Lounge or BOOK NOW  to get a top style in Chicago’s own River North neighborhood. We also provide full straight razor shaves, pedicures, manicures, facials, shoe shines and more.