5 coolest winter outfits for men #winter #style #fallstyle #mens #fashion #street #style

June 23, 2025

Best Winter Style Tips For Men

Home Men's Fashion Blog Best Winter Style Tips For Men

Winter is a season that brings its own unique style to the world of fashion. For many men, this is a particularly challenging time of year to dress for, as they have to balance warmth and comfort with style and sophistication.

In this blog post, we will discuss some winter style tips that can help men stay looking great even when the temperatures drop.

Layering

Layering is an essential aspect of winter fashion for men. Layering not only provides warmth but also allows men to experiment with different textures and patterns. A classic example of layering is wearing a sweater over a button-up shirt. This combination is not only stylish but also functional, providing warmth while giving a smart and polished look. Layering can also be achieved by pairing a denim or leather jacket with a weighted hoodie or a vest over a sweater.

When it comes to layering, it's important to choose pieces that complement each other. Choose colors that work well together and fabrics that are complementary. For example, a wool sweater pairs well with a cotton button-up shirt. Also, consider the fit of each layer. Layers that are too bulky can make you look bigger than you are, while layers that are too tight can restrict movement and be uncomfortable.

Accessories

Accessories are another important aspect of winter style for men. Hats, gloves, and scarves are not only functional but also add a touch of style to any outfit. Beanies, fedoras, and flat caps are popular choices for men's winter headwear. When it comes to gloves, leather gloves are a classic option that never goes out of style. Scarves come in a variety of styles and materials, from wool to cashmere, and can add a pop of color to any winter outfit.

When selecting accessories, consider the color and style of your outfit. Choose accessories that complement your outfit and add a touch of personality. Also, consider the function of each accessory. For example, if you live in an area with a lot of snow, consider investing in waterproof gloves and a warm hat that covers your ears.

Footwear

Footwear is another important aspect of winter style for men. A good pair of boots is essential for keeping feet warm and dry during the winter months. Leather boots are a classic choice that pairs well with almost any outfit. Chelsea boots and hiking boots are also popular options for men's winter footwear. When selecting winter boots, it's important to choose a pair that is both comfortable and durable, as they will likely see a lot of wear during the season.

When selecting winter boots, consider the weather in your area. If you live in an area with a lot of snow and ice, choose boots with good traction to prevent slips and falls. Also, consider the color and style of the boots. Choose boots that complement your outfit and add a touch of personality.

Coats and Jackets

Coats and jackets are the final piece of the winter style puzzle. A good coat or jacket not only keeps you warm but also completes your outfit. Pea coats, parkas, and puffer jackets are popular options for men's winter outerwear. When selecting a coat or jacket, consider the warmth and function of the piece. A coat that is too thin won't keep you warm, while a coat that is too bulky can be uncomfortable and restrict movement.

When selecting a coat or jacket, consider the color and style of your outfit. Choose a coat or jacket that compliments your outfit and adds a touch of personality. Also, consider the fit of the coat or jacket. A coat that is too tight can be uncomfortable, while a coat that is too loose can make you look bigger than you are.

To help you further... I've curated 5 coolest winter outfits for you.

Best Winter Outfits For Men

DIY Guide To Building A Perfect Capsule Wardrobe For Men. Click Here To Learn More

Outfit 1

This first one is perfect for a lighter winter. It is a balanced, classic look with a minimalistic charm to it. The white tee and the white sneakers maintain the color palette of the look. Of course, you can throw in many different forms of layers with a look like this one – but because we are trying to style an outfit for a lighter winter, we will stick to one classic, staple.

The denim jacket here is in a beautiful blue-grey shade, which approaches the darker palette of winters, balancing out the lighter shade of the rest of the outfit. This jacket does not have the cut of a denim jacket though. It is a blouson denim jacket. You can complete the look with some fitted denim trousers.

Outfit 2

We cannot talk about winter jackets without mentioning the biker jacket. Nothing has such an effortless edge to it as the biker jacket. This is in a classic black color, making this outfit an almost-all-black look, save for the little peep of white from the tee and the sneakers.

This helps break the monotony. There is a third layer to the outfit here, the black hoodie, that makes the look perfect for a more intense winter. Of course, most people steer clear of accessorizing with so many layers, but you can add a touch of experimentation with a belt chain. But, since the biker jacket will already have a number of chains, make sure the belt chain is sleeker.

Outfit 3

This is the most underrated member of the jacket family – the varsity jacket. Because they are associated with a slightly younger age group, most men steer clear of this jacket themselves. However, the varsity jacket has one of the most charming silhouettes, because it can be really warm without interfering with the overall fit of the look.

With varsity jackets, you get a wide range of fabrics, so if you want something with a similar shade of red, do not go for glossier fabrics. You can style it with a grey hoodie underneath, some pale blue ripped denims and a pair of white sneakers.

Outfit 4

If you are looking to style an outfit for a really intense winter, go for a puffer jacket. Because of their puffed nature, puffer jackets are irreplaceable when it comes to keeping you warm. The trick with puffer jackets is to keep every other element of the outfit really well fitted, so that the silhouette remains neat.

Again, puffer jackets come in a wide range of colors. So, if you are feeling a little unsure about it, go for an all-black combination. You can style this with fitted black trousers, white sneakers and a belt chain – if you want an element of edge.

Outfit 5

No list about winter outfits can be complete without mentioning the most flexible element of winter wardrobes – woolen scarves. These are really flexible when it comes to the different ways you can wrap them.

The best part though is that if you feel like your outfit has too many colors, you can just throw in a solid-colored scarf to make it look balanced. Style this with with a grey tee, black jacket, a checkered red-and-grey shirt and black trousers.

Outfit 6

The best thing about street-style looks is that you can go for some unconventional choices. You can have, for instance, a checkered muffler scarf styled with a biker jacket. Most people would not think of these two together, since biker jackets have a considerable number of chains on the front and that is one of its main attractions – so why would you hide that, right?

Well, the muffler scarf can actually accentuate that. You just have to choose a lighter scarf, one that isn’t too stiff in the way it falls on you. Pair it with a simple white tee and some black trousers.

Outfit 7

Here’s another laidback but classy combination. You can start with a simple white shirt and some beige trousers. You can also roll up the trousers a little to make the look even more sporty. The sneakers work really well with this look, and the rolled-up trousers draws more attention to it.

To complete this look, go for a grey muffler scarf and a mid-length black jacket. Make sure the jacket isn’t too long, and that the length of the scarf isn’t too short. This look is a bit of a throwback to the 90s, when looser silhouettes were in fashion, so go for a more relaxed fit with this.

Outfit 8

With this next look, we are going for lots and lots of layers. You want all of those layers to sit on each other without ruining the overall silhouette, so pay attention to the fits of the individual elements when you are picking them. For the base layer, you have a white shirt and some fitted black trousers.

You can add a grey mélange sweater to it. And then layer that with a mid-length beige overcoat, and a grey woolen scarf to complement the sweater. Finish the look with a grey beanie and white sneakers.

Outfit 9

This one is pretty easy to style, especially because each of these elements in this look is a classic, which means they will be available very easily. The base is very simple, classic white tee and black trousers. There are many different ways of styling this. Pretty much every kind of overcoat goes well with this look, as do a variety of scarves.

However, you can go for a classic combination like this. You can go for a double-breasted tweed overcoat, and a woolen scarf with a large checkered pattern. The block pattern of the scarf and the texture of the tweed jacket complement each other really well. With a look like this one, you want to keep the accessories to a minimal, and add a pair of white sneakers to finish the look.

Outfit 10

This is a really elegant look, one that adds a pop of color to the otherwise neutral palette. The grey turtle-neck sweater will accommodate some layers underneath, so rest assured about the warmth of the outfit. It will be very comfortable. The dark grey denims maintain the moody vibe of the look.

The brown boots add a hint of contrast to it, but the main contrast comes from the red puffer jacket which adds a dash of brightness to the look. It looks great even as an accessory thrown over your shoulders. If you are going to include the red jacket in your look, you can leave it a little open to make the grey sweater visible.

Outfit 11

The best thing about a look like this one is the base of the look. The turtleneck woolen pullover is one of the best pieces to have in your wardrobe. They are fashionable and they are very warm, making them perfect for winters. The one in this outfit, has some broad horizontal stripes for the pattern with a bright block of rust red on the top.

These pullovers are usually quite voluminous in themselves, so if you are going to add a sleeveless puffer jacket to it on top of this like the one here, make sure you check the fit. Add a pair of simple faded denims to complete the look. This will also contrast with the darker colors of the look.

Outfit 12

This is a really great example of how to take a pretty simple and basic summer look and add a layer of charm to it. The base of this look is actually really great for a base across the seasons. The white tee is comfortable in its fit, and the faded grey denims are also a classic that you can add to your wardrobe.

The star of this look, of course, is the bright red puffer jacket. Puffer jackets usually already have a pattern because of their structure, but this adds one more layer with blocks of black with gels nicely with the rest of the colors.

Outfit 13

This is one of the most fashion-forward looks on this list. Yes, it can be a little tricky to style because the entirety of its impact depends on one particular element. The base, with a white shirt and ribbed blue denims, is a classic, of course. The main element here is the long overcoat – the one here has a faded Madras checks pattern on it.

This is one of the most classic checks, and because of the colors and its long flowy nature, it can look really impactful. If you are going for a long coat, especially ones that go beneath the knees, make sure they are too stiff. Finish the look with a pair of white sneakers.

Outfit 14

Here’s another example of a checkered look, and this is more reason why one should really experiment with some checks. The base of this look, a grey rib knit pullover and some dark trousers, is pretty straightforward. The star of the look is the overshirt.

This is not so heavy on the fabric as the other overcoats in this list. The checks on it, Glen checks as they are called, are a classic. And they have been a mainstay of overshirts through several decades now. The lines of red in the overshirt add a lot of charm to the look.

Outfit 15

For the final look of this list, we have yet another outfit with a phenomenal pattern. If you aren’t too big on checkered patterns, you can go for a slightly different pattern as well. The base of look is a staple – a white shirt and pair of ripped denims, with some brown boots.

The brown jacket has a faded, vintage pattern on it, with the white stripes on the sleeves and the dramatic collar on it adding edge to the look. Keep the look neat with minimalistic accessories.