4 Outfit Ideas for Winter | Men’s Winter Lookbook

Looking for some outfit ideas for winter? Here are four winter outfit ideas for men who want be warm and stylish during the cold season.

Just like fall, winter is all about wearing layers. Layering up is essential for staying warm when it’s freezing cold outside, and it also looks super stylish.

The big difference between winter and fall style is how much insulation you need. For many people, winter weather requires extra protection against cold temperatures, wind and precipitation.

This includes your feet, of course, and the best way to keep your feet feeling and looking great during winter is to wear boots.

You’ll see boots from one of my favorite brands, Thursday Boot Co., throughout this post. I love this brand and highly recommend checking them out if you need a new pair of boots.

If you’re trying to decide which type of boot is right for you, check out my video about the three best types of boots for men.

Another different between fall and winter is the color palette.

There aren’t any hard and fast rules about which colors you can and can’t wear during certain seasons.

But, in general, winter is usually associated with darker, less saturated colors and tones like grey, black, charcoal and navy. Camel is also a great color for winter.

You’ll see these colors appear throughout my outfits, both casual and formal.

There’s nothing inherently special about these outfits. They’re not trendy or anything like that. In fact, I’ve owned everything I’m wearing in this look book for years.

It looks good because it fits well, and the colors work together. And it suits my preferences and personality, so I feel great in wearing it.

Of course, you should use these outfits as a starting point. Put your own spin on these outfits by changing the colors or adding different accessories.

Okay, let’s get into the outfits, starting with the most casual:

Outfit #1: Casual Layers (dark)

Perfect for: winter walks, lazy Sundays, working from home

If I had to wear one outfit all winter, this would be it. The components are pretty simple: a flannel button up shirt worn over a cotton henley (mostly for warmth), with a slim fit parka on top and dark wash jeans on bottom – finished off with a sturdy pair of dark brown leather work boots.

Of course, you could thrown on a scarf, hat and gloves as needed, but with a parka like this one, it’s probably not necessary.

Outfit #2: Casual Layers (light)

Perfect for: casual Fridays, running errands, coffee date

Just because it’s winter doesn’t mean you have to wear all dark colors all the time.

This outfit is a slightly different take on the first one.

Even though the color palette is lighter, it has a slightly more dressed up feel, although it’s still very casual.

This getup is comfy, warm and effortless. Plus, it maintains the streamlined, low contrast look that flatters the shorter build (because the light grey sweater is similar in tone to the medium wash jeans).

I love wearing tan suede Chelsea boots with lighter wash jeans. They work for casual looks like this, and they’re very easy to dress up.

For example, just swap the parka for a camel wool top coat, add a couple of tasteful accessories, and you’re ready for date night!

Outfit #3: Smart Casual

Perfect for: going out, parties, date night

I know some people don’t like mixing black and navy, but I think it can be a sophisticated combo if done correctly.

This outfit, for example, uses charcoal grey, black and navy to create a mature, elegant feel that’s perfect for hitting the town with friends (or a date).

This double layer topcoat has a lining built in, but you could simulate the same effect by wearing a light vest under a regular, single-layer topcoat.

Simple, fitted, black wool gloves are the icing on the cake here.

Of course, if the midnight suede chukkas with black jeans aren’t doing it for you, you could swap them out for a pair of tan Chelseas.

Black and tan is a classic color combination that almost always looks great. You could play up this combo by wearing a camel top coat instead of a grey one.

The choice is yours, my friend!

Outfit #4: Business Casual

Perfect for: the office, holiday parties, church

This type of outfit – flannel wool trousers, merino wool v-neck, cotton dress shirt – was my go-to winter getup when I worked in an office.

The grey and navy color palette is always a safe bet, but you could change it up to suit your personality and skin tone.

You could also wear black leather Chelsea boots instead of black Oxfords.

But for this kind of outfit, it’s crucial to have a formal coat (like a top coat). Despite what you see a lot of guys doing these days, it’s really not appropriate to wear a casual coat (like a parka or ski jacket) with this kind of outfit.

A wool top coat creates a much more cohesive look, and it will set you apart from the pack, in a good way.

Similarly, a pair of plain black gloves works best. Just make sure to get a pair that fits your hands!

Your Turn

I hope this look book gives you some ideas and inspiration for staying warm and stylish this winter.

Questions or comments? Leave them below!