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The Editors
Updated on October 11, 2021
19 of 20

19. Men’s Messy Hairstyle With The Box Top

spiky messy hairstyle for men

Helga Esteb /

The box top hair cut is great for men with rounder face shapes because it lengthens the face and causes it to look slimmer. It also draws the eye to bone structure and gives more definition to your appearance! Winnie, a country musician, says that “this hairstyle is the trend amongst many country musicians and I love it! There is something about a box top hair cut that makes your heart melt.”

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19 of 20

We, as women, love a nice hair cut on a man. There are thousands of styles to choose from. However, this article will be focusing on 20 messy hairstyles that look phenomenal on men. 20 women were surveyed and gave their opinion on why they love their selected hairstyle.

Men’s Messy Hairstyles As Women See Them

Guys, pay attention! This is coming straight from the mouths of the babes. Names have been changed.

1. Tousled Top And Short Sides

men's medium messy hairstyle

landmarkmedia /

Kelly, a fashion enthusiast, says she loves the look of tousled hair on top. She says, “I think that this look is very diviner. The way his natural waves fall gently above the brow bone is just entirely too sexy.” It’s quite obvious that a nice natural ‘do is very appealing.

2. The Refined Faux-Hawk

Aria, a clinical nurse, feels like the refined faux-hawk is what rocks her boat! She says, “Yes! I’m totally feeling this look. The fact that it’s shorter on the sides but relatively long at the top is hot! Yet, it’s not too dramatic in length difference, so it’s more of a refined faux-hawk.” You can’t help but agree that this hairstyle is great!

men's messy faux hawk hairstyle

Helga Esteb /

3. Men’s Messy Hairstyle With Feathered Ombre

Lillian, a party hardy socialite, feels that this hairstyle is the cream of the crop. Having described it as an “ombre escapade”, she feels that the gradient affect of the dye job, truly brings out the man’s eye color. She says, “I think that all men should try an ombre escapade! As far as the picture goes, the snowy tips really bring out his ice blue eyes.”

Mens messy hairstyle with a highlighted quiff

Joe Seer /

4. Choppy Parted Curls

This style was named “the curly cusp” by die-hard dancer, Janet. She believes that this style provides the best of both worlds! She says, “The curly cusp is the highest mix of formality and casualness. The way it’s tucked behind the ears and parted to the side makes it formal but the messy curls make it casual. It is the truth!”

men's messy blonde hairstyle

Helga Esteb /

5. Medium Men’s Messy Hairstyle – The Side Swept Shag

“This hairstyle is wonderful! It says ‘Take me! I’m here.’ The way it’s effortlessly tossed over to the side is so tempting. It’s like a beautiful trouble”, says Lora, a happy housewife. The preferred side swept shag draws your attention to the face, while accentuating the jaw line. No wonder she loves it!

men's messy hairstyle short-to-medium length

Tinseltown /

6. Short Layered Waves

Nicknamed as “Choppy Seas,” this hairstyle won the hearts of many. Due to the stiff waviness and choppy layers, it struck a few hearts. Rani, a band guitarist, says “I think it’s totally cool. It’s different but still hip. It has a nice edginess without being too much.”

men's messy wavy hairstyle

Photo Works /

7. Men’s Messy Hairstyle – Spiked 90’s High-Top

Maggie, a surrealistic artist, calls this hairstyle “the Stray Away.” With pieces falling in every direction, the name is spot on! Yet, it’s still just as appealing. Maggie says, “I hate to see a guy who’s too uptight. This hairstyle says ‘Hey I’m easy going but I have a hidden wild side. What girl doesn’t want that?”

men's messy spiky hairstyle

cinemafestival /

8. Short and Slanted

This short and slanted style is simple yet unique. With short, spiked strands that have been combed in a diagonal direction, it is very fun and funky! Amber, a graduate student, has this to say, “I would adore if my boyfriend wore that hairstyle! It’s zany but not too much.”

short messy hairstyle for men

ChinellatoPhoto /

9. Men’s Messy Hairstyle With Feathered Waves

“This hairstyle alone is enough to drive me crazy! It’s so devilish and handsome that it just screams ‘Polished Rebel’! The curls, the cut, everything.” That is the quote of indie enthusiast, Miranda. This style appeals to her with its charming curls and devilishly dark hue.

men's messy medium hairstyle for curly hair

Helga Esteb /

10. Medium-Long Shag With Bangs

Katie, a competitive cheerleader, says “Yes! This haircut is so ‘box next door’. It reminds me of the Ashton Kutcher days. I think that if a guy wears this hairstyle, it just makes him seem so inviting.” Apparently, this friendly style is enough to put a girl at ease. Maybe it’s even enough to have the chicks come to you!

men's messy hairstyle for straight hair

DFree /

11. Wet and Wild Men’s Messy Hairstyle

“OMG! Swim Fan! This hairstyle gives me the illusion that the guy is athletic, a swimmer because the hair looks wet. It also makes me feel that he’s carefree because there is no rhyme or reason to the styling.” This quote is from Emma who is a competitive athlete. The effortless shine from this hairstyle is more than alluring!

men's disheveled hairstyle

Helga Esteb /

12. The Modern Mohawk

This modernized mo-hawk is adored by many women! One of which is sports enthusiast, Opal. She claims that this hairstyle is the epitome of romantic appeal. She says “If I had a guy approach me with that hairstyle, I would just melt! It’s like the epitome of sexy.” Well, it’s clear that the closely tapered sides and neck-length tail must be working!

men's Mohawk hairstyle


13. Men’s Messy Hairstyle – Silver Layered Curls Combed Back

Wisdom is always an attractive quality in a man. This hairstyle is perceived by women as a physical representation of that trait. Hannah, a medical stewardess, feels that “this ‘do is cool. It’s so much more attractive to see an older gentleman who is mature enough to wear his natural hair proudly with no dyes!” Surely, it’s a good look to let your natural grays gracefully grow in!

men's combed back messy hairstyle

DFree /

14. Straight Spiked Faux-Hawk

This hairstyle is a great combination of edge and class! Gretchen, a singer songwriter, has the following to say, “I think that this look is very retro 1998! It can be easily paired with a blazer or a graphic tee. It’s spiked and spiffy! This is the ultimate rocker girl’s dream.”

mens faux hawk hairstyle

Tinseltown /

15. Men’s Messy Hairstyle – Low Ponytail

The low ponytail has been around for centuries yet it never gets old. It looks great on men, women, youths and adults! Yahveh, an aspiring broadcast journalist, says “I love long hair on men. But, it’s something about when they have it tied up in a low pony that just really attracts me! It shows that they’re strong but neat.”

mens long messy hairstyle

Helga Esteb /

16. Tapered Back And Long Bangs

Male bangs have been trending on and off since the 1990’s. This hairstyle is great for men who want to have a very individualized haircut. With long bangs and a tapered back, it frames the face while maintaining a light feeling. Teresa, a child care worker, says “I definitely feel those male bangs are hot! They make a man more mysterious, which in turn makes him three times more attractive!”

men's messy hairstyle with elongated quiff

Helga Esteb /

17. Men’s Messy Hairstyle – The Messy Bun

“Caveman chic is what I like to call it,” says Queenie, an aspiring fiction author. “The messy bun is very hipster happy and is the mating call of male hairstyles!” Although the messy man bun is quite simple to achieve, it has an impeccable impact on women. It’s almost an instinctual attraction!

men's messy hairstyle for long hair

Helga Esteb /

18. Tapered Sides And Volume on Top

Katherine, an aspiring scientist, has a real soft spot for sweethearts. She says that this particular hairstyle, the lightly feathered top and short cut sides, is her go-to style to look for with men! She quotes, “I feel that every girl wants a guy who’s going to be nice to her. There is something about this look’s simplicity that is cute and comforting. It gives me the impression that he’s got a sweet personality to match.”

short men's messy hairstyle

Helga Esteb /

19. Men’s Messy Hairstyle With The Box Top

The box top hair cut is great for men with rounder face shapes because it lengthens the face and causes it to look slimmer. It also draws the eye to bone structure and gives more definition to your appearance! Winnie, a country musician, says that “this hairstyle is the trend amongst many country musicians and I love it! There is something about a box top hair cut that makes your heart melt.”

spiky messy hairstyle for men

Helga Esteb /

20. Spiked Length On Top with Long Bangs and Buzzed Sides

“Wow, it’s like there are so many angles and lengths within one hairstyle that you can’t help but be intrigued! I think that if a guy has the courage to rock this type of hairdo that he is someone I’d wanna know. It’s gutsy!” This quote is from Amie, an aspiring actress. With heavy layering, long bangs and tapered sides, this haircut is very busy but the boldness shows women that you are aimlessly individual and that you strive to be strange.

men's messy hairstyle with a quiff

Helga Esteb /

There you have it! These messy hairstyles are very appealing in their own ways. Now, it’s your job to figure out what assets are more important to you in a hairdo. Whatever you choose, be sure to try something new because it’s always good to venture outside of your comfort zone. Just don’t lose sight of your personal style!

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