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30 Easy-to-Maintain Winter Hairstyles for Men in 2023

Home » 30 Easy-to-Maintain Winter Hairstyles for Men in 2023

January 22, 2023 By Lara Thompson Leave a Comment

When we’re talking Winter Hairstyles for Men, we’re looking at hairdos that don’t take much effort.

When that beanie comes off, every man wants a winter haircut they can just quickly tidy up with a suave wave of their hand.

So you’re going to see a lot of messy haircuts from here on out. But not only. Let’s take a look!

1. Simple French Crop with Tight High Fade Winter Hairstyle for Men

We’re starting off with a style for kinky hair that goes perfectly well with the winter chill! You can drop a beanie over this winter hairstyle any day of the week and it’ll come off looking fresh. Go for something longer, however, if you don’t like the cold!

a man wearing a dark blue jacket with a French crop winter hairstyles for men
Source

What to ask for: French crop with high fade

2. Long and Thick Dreadlocks

Dreads are not very comfortable when the warm weather hits, but come winter and you’ll be loving the warmth they give you. Many men actually love going out without any sort of cap, hat, or beanie. Me, I’m partial to some head coverage.

a man with Long and Thick Dreadlocks Winter Hairstyles for Men
Source

What to ask for: Just basic dreads, nothing too fancy, you just need to let your hair down

3. Messy Curly Side Sweep with Subtle Part

Now, normally parted hair in winter is a no-no because you’re going to ruin it. However, this medium fringe will work well for curly-haired dudes. Just because curly hair looks great however you want it – so be proud of your curls!

a man with Messy Curly Side Sweep with Subtle Part winter hairstyles for men
Source

What to ask for: Side parted thick fade with side swept curly messy fringe

4. Justin Timberlake’s Basic Cut with Stubble

This Justin Timberlake hairdo won’t put you into outer space, but it’ll carry you through winter and that’s why you’re here, right? For winter hairstyles. There’s nothing much to say really about this hairdo – simple, short, and a bit of a stubble.

Justin Timberlake's Basic Cut with Stubble while wearing a jacket winter hairstyles for men
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What to ask for: Simple, short cut

5. Simple Slick Hair in the Style of Daryl Dixon

Well if you want a low upkeep winter hairstyle, there’s no better way to go than Daryl Dixon’s hair from the Walking Dead. Granted, this photo is not of Daryl, but it’s the exact same style and if it works in a zombie apocalypse, it’s going to get you through winter, crossbow, or no crossbow.

Daryl Dixon's simple slick hair winter hairstyles for men
Source

What to ask for: Just a trim

6. Wavy Medium Length Hair with a Short Beard

Want a dreamy boy look AND something that works well in winter? Here you go! You can’t go wrong with this one. It’s going to look a bit all over the place after you go out, but hey – it’ll be cool and wavy anyway.

a man with Wavy Medium Length winter hairstyles for men in a sweater
Source

What to ask for: long pompadour with a short beard

7. Wavy Mess Winter Hairstyle for Men

There’s no way people won’t like this wavy bad boy mess. It’s got everything – stylish waves, short stubble, simple sides, dreamy eyes.

a man with wavy mess winter hairstyles for men wearing a black turtle neck
Source

What to ask for: Trim the sides and shape it so it doesn’t look too untidy

8. Henry Cavill’s Medium Curly Hair

Henry Cavill is the internet’s crush in this day and age – if you look over Reddit, you’ll find swaths of ladies swooning over his luscious hair. So why not try to look a bit like him?

Henry Cavill Medium Curly Winter Hairstyles for Men
Source

What to ask for: Medium curly hair like Henry Cavill

9. Shaggy Wavy Hair

This one doesn’t necessarily require you to go to the barber. You can just get a haircut in the middle of October and let your hair grow from there.

a man with Shaggy Wavy Winter Hairstyles for Men
Source

What to ask for: Just a trim

Over 40 more hairstyles for men with wavy hair!

10. Overgrown Pink White Undercut Winter Hairstyle for Men

Ok, this might not be as easy to maintain as the other ones on the list, but we’re in love with the hair color. It works so well with winter’s white landscape – who wouldn’t love it?

a man with Overgrown Pink White Undercut winter hairstyles for men
Source

What to ask for: White color with pink roots plus an undercut

11. Simple Medium Shape Up

Precise, simple, short sides work well, but not too short so you’ll freeze during winter’s cold embrace. This hairstyle is a good combo of short hair and not too short.

a man with Simple Medium Shape Up Haircut
Source

What to ask for: Basic shape up

12. Basic Slick Back Winter Hairstyle for Men

Is this the mafia look? This is the mafia look. Or not. Depends on what the boss man wants. Anyway, all that hair gel will keep your hair looking neat throughout winter.

a man with Basic Slick Back style in a tuxedo
Source

What to ask for: basic trim and lots of gel

13. Simple Short Curls with Basic Drop Fade

You can’t go wrong with simple, short, afro-textured curls. What works best with this look is the medium beard. Especially in winter, it’ll help keep your face warm.

a man with Simple Short Curls with Basic Drop Fade
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What to ask for: Simple curly hair with drop fade and a trimmed beard

14. Shaggy Blonde Curls

More of a high school look than anything, these curls will get you into the most high-brow end-of-year parties. Mandatory no beard.

a man with Shaggy Blonde Curls in a black suit
Source

What to ask for: Just a trim and a full shave

15. Short to Medium Curls Winter Hairstyle

The optimal length of curls to get at the barbershop. They’re not too long so as to seem unkempt, but not too short that the curls don’t form. Perfect for winter!

a man with Short to Medium Curls with trimmed beard
Source

What to ask for: Medium curls

16. Forward Swept Fringe Hairstyle

So dreamy, so messy, and so wintery! No matter what sort of headwear you wear over this hairstyle, it’ll look amazing after you take it off!

a man with Forward Swept Fringe in white sweater while holding a paint brush
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What to ask for: Simple, forward-swept fringe

17. Simple Salt and Pepper Pompadour with Beard

Going into winter hairstyles for older men, this look is stylish and old-fashioned, but still modern enough to be fresh today.

a man with Simple Salt and Pepper Pompadour with Beard
Source

What to ask for: Medium pompadour with a neatly trimmed beard

18. Extra Messy Shaggy Hair

This is almost a hobo look, but not quite because of the trimmed beard and neat clothes. You really need dapper, good-quality clothes to make it work the whole way. Bonus points – you’ll never go cold in winter (hopefully).

a man with Extra Messy Shaggy cut in a suit
Source

What to ask for: Just trim your won beard and go to the barber only when necessary

19. Short Simple French Crop

The angled crop is a neat look in the modern age. The short curls add a lot of sophistication to it, as does the pencil mustache! It’s a must-try look if you’ve got afro-textured hair.

a man with Short Simple French Crop wearing a black shirt
Source

What to ask for: Short French crop with a neatly trimmed mustache

20. Medium Dreads Winter Hairstyle for Men with Extra Stylish Beard

You can’t beat this look. Can you beat this look? We wouldn’t try, but be our guest! Don’t forget to send a photo. As we already said, dreads and beards are perfect together for that winter look and also for extra warmth!

a man with Medium Dreads with Extra Stylish Beard
Source

What to ask for: Medium dreads and an extremely neatly trimmed beard

21. Medium Dreamy Boy Waves

We’re mesmerized by this dude. Who is he? Can I get his number? Uhm, no reason. You just have to make sure you shave your beard regularly and go to the barber for a trim often.

a man with Medium Dreamy Boy Waves in a suit
Source

What to ask for: Just a trim and a shave

22. Wavy Mess with Stubble Winter Haircut

Don’t shave for three days at a time, leave your hair medium-length, and run your hand through your hair all carelessly like – do you even care? You should. But you should act like you don’t.

a man with Wavy Mess with Stubble
Source

What to ask for: you don’t need a barber for this one

23. Catwalk Curly Hair

All these men with flawless blonde curly hair on here – what am I doing wrong? The answer is nothing, you’re not doing anything wrong, you just need to wear it as you mean it. These curls are perfect winter hairstyles, so try it once and see how it goes.

a man with Catwalk Curly while wearing sun shades
Source

What to ask for: Simple curly trim, clean shave

24. Slicked Back Undercut with Bushy Beard Style

We had to have a traditional undercut here, so here’s this badass, suspender-wearing, bearded office Viking. The shaved sides might be a bit too short for winter’s chill, but if you want to be a real Viking you have to handle that thing.

a man with Slicked Back Undercut and Bushy Beard while wearing a long sleeve and a suspender
Source

What to ask for: Simple slicked-back undercut with shaved sides

25. Medium Afro Curls with Short Beard

Just a slight variation on the number 19 on our list. A bit longer, no more fade, and a simpler beard. The true trend this winter is going for the simpler style that works, but don’t take it from us, take it from him!

a man with Medium Afro Curls with Short Beard
Source

What to ask for medium afro curls, a short beard

26. Forward Swept Undercut Dreads for Men

Fuzzy, medium cut, forward-swept – these dreads look incredible. The undercut also helps make the look even tighter and more modern. If I were you, I’d bookmark this one!

a topless man with Forward Swept Undercut Dreads
Source

What to ask for: Dreads, undercut, forward swept (bring a picture)

Want more dreads? Check out this article!

27. Loose Medium Waves with Short Beard

While we keep going down the list, we’re getting to more and more wavy, shaggy looks. This one is slightly mullet-like and it works well. I don’t like the beard on this winter hairstyle, however – so you could drop it if you like, it might look better!

a man with Loose Medium Waves with Short Beard in a sky blue shirt
Source

What to ask for: Just a trim

28. Absolute Hot Mess Winter Hairstyle

I can’t describe this one any other way. I think it’s actually an overgrown pomp hairstyle. Why does it work for winter? Because however, you style it, it’s gonna look great!

a man with Absolute Hot Mess style with tattoos printed on the body
Source

What to ask for: A clean shave plus an overgrown pomp (might not even need a trim)

29. The Man Bangs Winter Cut

Yes, a man with bangs and a short beard. Does it look good? Of course. Do you dare to try the man bangs or would you defy the mighty bangs? Jukes aside, bangs are a favorite in winter because of the wispy look.

a man with Bangs
Source

What to ask for: Bangs and a short beard

30. Side Part with Slick Fringe for Men with Pointy Beard

The hipster look will always complement winter clothes with warm tones and scarves. The beard works especially well with overcoats.

a man with Side Part with Slick Fringe and Pointy Beard in his denim attire
Source

What to ask for: Long fringe with a side part and a pointy beard

Conclusion

Winter is the season when everyone’s hunting for presents. But what you should also hunt for is a winter hairstyle. We’ve put together the best we could find this season, which one do you like?

Let us know in the comments and if you decide to try one, send us a photo on Pinterest and we might even feature it somewhere!

Lara Thompson Menhairstylist
Lara Thompson

Lara has been working with us since the website launched. She is an accomplished hairstylist with years of expertise giving her clients the style they dream of. Lara is working on her own cosmetics brand and has certifications from some of the greatest hairstyling schools in her wallet. She is committed to leading an active life and specializes in men’s hairstyles, haircare, and coloring.

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