Last updated on December 15th, 2023 at 05:38 pm
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!
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.
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!
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.
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.
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.
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.
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?
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.
What to ask for: Just a trim
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?
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.
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.
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.
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.
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!
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!
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.
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).
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.
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!
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.
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.
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.
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.
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!
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!
What to ask for: Dreads, undercut, forward swept (bring a picture)
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!
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!
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.
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.
What to ask for: Long fringe with a side part and a pointy beard
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 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.