Men’s Casual Winter Outfits | How To Dress For The Coldest Months 2023

Winter is coming, and that means it’s time to start thinking about how to dress for the coldest months of the year.

While some men might be tempted to just wear a puffer jacket and call it a day, you guys know better. There are far better ways to dress in the colder months!

Today, I’m breaking out different casual winter outfits for men that will keep you warm and looking your best.

Best Men’s Casual Winter Jackets

A good jacket is the foundation of any effective winter wardrobe. When choosing a casual winter jacket, you’ll want to find one that is both stylish and functional.

A casual bomber jacket or a denim jacket are always good choices, but if you live in a particularly cold climate, you might want to invest in a thicker wool coat or parka.

The Bomber Jacket

A casual bomber jacket is the perfect piece of outerwear to take you from fall into winter. It’s great for layering over shirts and sweaters, and it will keep you warm without making you look too bulky.

Keep in mind that not all bomber jackets are perfect for winter weather. Suede is not the sort of fabric a man should wear during the colder months when rain and snow are on the menu.

However, a leather or waterproofed fabric bomber jacket can be a great option for guys who want to add a casual jacket to their winter wardrobe.

Parka Jacket

Parka jackets are awesome. They’re casual, they keep you incredibly warm, and they have that cool, casual vibe that every guy can pull off.

When shopping for a parka jacket, make sure to find one that is waterproof and has a fur-lined hood. These features will make it much easier to brave the cold weather in style.

For extra warmth, opt for a jacket stuffed with down. Down is a type of feather that is incredibly light and insulating, making it the perfect material for a winter jacket.

Don’t forget to pay attention to the length of the parka when you’re shopping. You want one that hits at about mid-thigh or lower, so it will keep your whole upper body warm.

Tweed Blazer

To some extent, tweed blazers are an all-year-round kind of garment. However, winter is when they really come into their own.

A well-fitting tweed blazer is the perfect casual piece of clothing to throw on over a shirt when it’s cold out. It will add an extra layer of warmth without making you look too bundled up.

When shopping for a tweed blazer, make sure to find one that fits well. Tweed can be a bit bulky, so you don’t want a blazer that is too big or boxy. If needs be, take your blazer to a tailor and have them alter it to fit your figure.

If you’re planning on wearing this garment when it’s REALLY cold, make sure to wear a thick jumper under your blazer when having your measurements taken. This will allow your tailor to make the necessary size adjustments without making your blazer too fitted to accommodate a thick knitted sweater underneath.

Pro tip: It’s also important to choose a tweed blazer in a dark color. Light-colored tweed just doesn’t suit the cozy vibes of the colder months!

Best Men’s Casual Winter Shirts & Sweaters

With jackets out of the way, it’s time to start thinking about what you’ll wear underneath. A casual button-down shirt is always a good choice, but if you’re looking for something a little warmer, a sweater is the way to go.

The choices are endless, so let me break out a few of my winter favorites below:

Knitted Turtleneck Sweater

A knitted turtleneck sweater is the epitome of winter style. It’s casual, it’s warm, and it looks great with just about anything.

Turtleneck sweaters are available in a wide range of colors and styles, so you’re sure to find one that suits your taste. Just make sure to avoid anything too bulky or heavy-looking. You want a sweater that will keep you warm without making you look like the Michelin Man!

One of my favorite styles of turtleneck sweater is the fisherman’s turtleneck. This style of sweater has a cool vintage vibe that look great with a tweed blazer and chinos!

It’s thick, textured, and warm as hell.

Merino Wool Sweater

If you’re looking for a smart-casual sweater that you can wear on its own or layered under a jacket, a merino wool sweater is a great choice. Merino wool is an incredibly soft and insulating fabric, making it the perfect material for a winter sweater.

When shopping for a merino wool sweater, look for one in a dark color. Dark colors are not only more flattering, but they also tend to suit colder weather better than lighter, pastel options. A dark burgundy merino wool sweater is one of my favorites to bring out when December rolls around.

As far as style goes, you’ve got two options:

1. Crewneck with a white undershirt
2. V-Neck with a button down underneath

Ultimately, the only difference between these two styles is formality. A crewneck sweater with a white undershirt underneath looks slightly less formal than a V-neck sweater worn with a shirt.

Cashmere Sweater

A cashmere sweater is the ultimate luxury item. It’s soft, it’s warm, and it looks amazing whether you’re wearing it on its own or layered under a jacket.

The same rules apply to cashmere sweaters as to merino wool sweaters. They’re similar in their styling, but cashmere is definitely more luxurious.

Wool Cardigan

A wool cardigan is another great option for men who are looking for a casual winter sweater. Cardigans are perfect for layering over shirts or under jackets and can be a great casual alternative to a blazer when worn with a button-down shirt and tie.

You don’t want a cardigan that is too loose or baggy as it will just look sloppy. The aim is to find a wool cardigan that look as though it’s been tailored to your body. Avoid anything that uses the term ‘oversized’ or ‘box fit’ as these garments will be too baggy for men interested in timeless style.

Best Men’s Casual Winter Trousers

As far as trousers go, you’ve got a few different options to choose from. The casual winter outfit with trousers I typically reach for consists of a pair of dark wash jeans, chinos, or wool trousers.

Let’s start with the most casual option first:

Jeans

Regardless of the season, jeans are always a good choice for casual style. They’re comfortable and they go with everything.

However, when choosing a pair of jeans for winter, look for a darker wash. Darker washes tend to look more formal than lighter washes and are also more flattering.

One of my favorite styles of jeans for winter is the raw denim jean. Raw denim is a type of denim that is left untreated, meaning it will age over time and develop a unique patina.

Raw denim jeans also tend to be more fitted than other styles of jeans, so they’ll look great whether you’re wearing them with a casual shirt or a more formal sweater.

Chinos

Chinos are a great option for men who want something that is casual but still looks put-together. Chinos are typically made from a cotton-twill fabric and have a casual yet slightly dressier feel than jeans.

As with jeans, when choosing a pair of chinos for winter, look for a darker color. Darker chinos will be more flattering and will also go well with the rest of your casual winter outfit.

To avoid looking too formal in your chinos, avoid anything that is too slim-fitting. Instead, opt for a pair of chinos that are more slim-straight in their fit.

Wool Trousers

Wool trousers are another great option for casual winter style. They’re warm, they look great, and they can be dressed down if you ensure the rest of your outfit is casual in appearance.

When choosing a pair of wool trousers, make sure to find a pair that is fitted but not skin-tight. You don’t want anything too baggy or loose as it will just look sloppy.

As far as design goes, you’ve got two options: flat front or pleated. I personally prefer a flat front as it looks more modern, but ultimately the choice is up to you.

Best Men’s Casual Winter Shoes

When considering which men’s shoes are best for the colder months, you’ve got a few different options to choose from: sneakers, boots, or shoes.

It seems obvious, but when it comes to winter shoes it’s essential you consider how waterproof and warm each style of footwear is. After all, sandals are great at the beach, but could cause you to catch frostbite if worn during the winter months!

Winter Boots For Men

As far as casual winter footwear goes, boots are always a good choice. Not only will they keep your feet warm and dry, but they can also be dressed up or down depending on the occasion.

There are a few different types of casual boots you could consider:

• Chelsea Boots – a classic style of boot that has been around for centuries. Originally designed as riding boots, Chelsea boots typically have a lower heel and an ankle-high shaft.
• Leather Chukka Boots – another classic style of boot, chukkas are typically made from suede or leather and have a casual, desert-inspired look. Obviously, opt for leather during the winter – suede won’t hold up against the harsh rain and cold.
• Derby Boots – Derby boots are characterized by their open lacing system. They have a timeless look that never goes out of stylish and act as a more formal option for guys looking to add some smart-casual flair to their outfit.

Winter Sneakers For Men

While sneakers might not be the first thing that comes to mind when you think of casual winter footwear, they can actually be a great choice.

Look for a pair of sneakers made from waterproof materials such as Gore-Tex or neoprene. These materials will help to keep your feet dry and warm even if you step in a puddle or snow.

As far as style goes, you’ve got a few different options:

• High-Top Sneakers – provide more coverage and therefore more warmth than low-top styles. They also tend to have a more rugged look which makes them ideal for casual winter outfits.
• Low-Top Sneakers – a more casual style of sneaker that can be dressed up or down depending on the rest of your outfit. A better option for gents looking to dress down their wool trousers.

Winter Shoes For Men

Shoes are a great option for casual winter style if you don’t mind sacrificing a little bit of warmth. There are a few different types of shoes you could consider:

• Loafers – a slip-on style of shoe that is typically made from leather. Loafers come in both casual and formal varieties, so make sure to choose a pair that will complement the rest of your outfit. For winter, I’d stick to chunky sole, leather loafers.
• Oxfords – Oxfords are characterized by their closed lacing system. They tend to have a more formal look but can be dressed down when worn with the right outfit. As with loafers, make sure to choose a casual pair of oxfords with a chunky sole.
• Brogues – Brogues are a type of casual shoe that is characterized by its perforated detailing. They come in both low and high-top varieties, so again, make sure to choose a style that will complement the rest of your outfit.

Casual Winter Outfit Ideas For Men

Putting all of these different winter garments together can be tough. After all, there’s plenty of option when it comes to casual cold-weather clothes, and creating the perfect casual winter outfit for men can seem impossible.

Don’t worry gents, I’ve got you covered. Below, you’ll find a few of my favorite cold weather outfits that incorporate many of the garments I mentioned above. Copy these exactly or use them as inspiration for your own style – either way, this should give you the winter outfit jumpstart you need.

Weekend Casual Winter Outfit

This casual winter outfit is perfect for running errands, grabbing coffee with friends, or just relaxing on the weekend. It’s comfortable, stylish, and most importantly – warm.

Start with a pair of charcoal-gray jeans and a navy blue wool sweater. Next, add a pair of brown leather boots and a black parka coat. Finally, accessorize with a beanie and scarf in complementary colors.

Casual Date Night Winter Outfit

Looking to up your date night game this winter? This casual date night outfit will do the trick. It’s dressy enough to impress your date but still casual enough to keep things relaxed.

Begin with a pair of dark blue jeans and a white oxford button-down. Add a grey blazer and a burgundy scarf to finish.

Casual Winter Office Outfit

This casual office outfit is ideal for days when you need to dress down your usual workwear. It’s comfortable, stylish, and professional – everything you need to get the job done.

Start with a pair of navy blue chinos and a checked Oxford button-down shirt. Add a light grey sweater and a pair of brown leather brogue Derby shoes. Then, accessorize with a patterned tie and a leather jacket

Snow day casual outfit

There’s nothing better than a casual snow-day outfit. This one is perfect for playing in the snow or just relaxing at home.

Start with a pair of black jeans and a white thermal Henley shirt. Add a navy blue parka coat and a pair of black boots. Finally, accessorize with a beanie and scarf in complementary colors.

To summarize, men’s casual winter appearance is all about balancing functionality and style. Carefully select pieces of clothing and footwear that not only keep you warm but also maintain a sense of personal style.