At first, the cold weather that accompanies the changing of the season is a welcome relief from the heat.
The leaves start to change, the air turns crisp, and the first snowfall has an enchanted quality.
And these changes bring the well-dressed man's favorite time of the year.
I typically find myself so receptive to the first bit of cold weather that I just throw on my top coat and let it fly unbuttoned for the first couple of months.
But the freezing temperatures soon overstay their welcome.
By the time January rolls around, what was a welcome experience starts to seem more like a punishment.
At that point, winter attire becomes more about survival than experiencing and enjoying the season.
For the the most extreme weather, I rely heavily on my heavy duty parka.
But to extend its functionality well below freezing, some cold weather accessories are a necessity.
A Note on Materials
I've mentioned before how much of a gear junkie I am.
I'm an avid camper and hiker and have spent countless hours reading Backpacker Magazine, survival books, and outdoor websites.
A big topic of discussion in all of these sources is clothing material.
People get as extreme as to say, “you sweat, you die” and “cotton kills” in regard to moisture management.
I like to take what I learn to the trail and experiment with various materials and designs. I've been able to use this knowledge to help make better casual wardrobe choices.
Living in the city, choosing one material over another isn't exactly a life or death situation, but it can contribute greatly to comfort.
So in each category, I've included suggestions as to which material works best.
A Note on Patterns and Colors
A major deciding factor here will revolve around your chosen outerwear.
If you wear a topcoat with a prominent pattern or a boldly colored parka, it would be best to go with neutral colors and patterns for your accessories.
Alternately, if you have a solid navy, black, or gray peacoat or duffle, going with a striped or plaid hat and scarf in interesting colors would be a fine choice.
It's all about having the foresight to plan your wardrobe purchases and to strike an elegant balance between personality, functionality, and simplicity.
While the old belief that, “you lose most of your body heat through your head” may not be the most accurate, it sure feels like it.
Adding a hat to your winter wardrobe can help you handle temperatures 10 – 20 degrees colder than a coat alone.
For cold weather hats, synthetic or cotton works great because they can usually be washed without special care.
This is a necessary quality if you intend to wear your hat while shoveling snow or other sweat-inducing activities.
I would avoid something labeled “wool” unless it has a soft lining like the option from Coal below.
I had an unlined wool hat a few years back and it drove me absolutely insane.
The entire time it was on, I was constantly rubbing my forehead while wearing an annoyed expression.
However, if you opt for cashmere or merino wool, although still types of wool and more expensive, they'll be very comfortable and look luxurious.
If you're like me and want to (or need to) skip the hat hair, grab a pair of these. They actually work so well that I have to periodically take them off to let my ears cool.
To me, gloves are an essential component of a fully functional cold weather wardrobe.
Chicago gets so cold that my hands stay chilled even if I have them gloved and tucked in my coat pockets.
So leaving my digits exposed would likely mean frostbite before I could walk half a mile.
For elegance, there's no substitution for leather.
Leather gloves are durable, refined, and badass all at the same time. Plus, they get better the with age.
For a more casual look you could go with some type of knit wool, but really, leather is where it's at.
More often than not, leather gloves will have some type of lining in either wool, merino wool, cashmere, or a synthetic.
I haven't run into a lining material that didn't perform exactly as intended.
As a teenager, scarves were too fussy and feminine looking for my tastes. But I have changed my tune as I've grown older and wiser.
I really enjoy wearing scarves now and like to think of them as neckties for outerwear.
It's one of the more “safe” arenas for men to experiment with bold colors and patterns.
I'm actually amazed at how much warmth can be achieved by adding a scarf to your cold weather outfit.
Insulating those major arteries and keeping the wind from going down the front of your coat really has a bigger-than-expected impact.
This piece is going to be wrapped around your neck, so having a comfortable material is essential.
My biggest piece of advice here is to avoid low-priced wool scarves.
The cheapest scarf made from cotton, synthetic, or merino wool is going to be just fine and expensive wool or wool blend scarves will also be comfortable.
It's just the bottom shelf wool scarves that are going to feel like a military blanket rubbing your skin away.
One thing shopping for scarves has made me realize is that there are some really impressive synthetics out there.
Seriously, even when I read the label that says “cashmere feel” I still can't believe it isn't the real thing.
If you're working on a budget, a scarf labeled as “cashmere feel” would be my first choice.
I love a good pair of boot socks. They help turn an uninsulated pair of boots into something a little better suited to sub-zero conditions.
They also act as standalone slippers when the boots come off.
I've had bad luck with the vintage-inspired “camp socks”, the ones that are made of loosely knit wool yarn. These socks look great but they lack the elasticity of modern day socks.
It drives me completely crazy to have my socks sag, wrinkle, and fold inside my boots.
I've had much better luck with workwear socks or those made for hiking (if you can find tastefully styled options).
The only thing that should be avoided here is cotton.
I've had some really thick cotton boot socks in the past and while they felt cozy when first put on, it was downhill for the rest of the day.
Cotton doesn't handle moisture very well and a foot trapped in a boot for 8-12 hours is going to sweat.
The thick cotton socks I had became matted and wet feeling within a couple hours. This left my feet feeling cold and gross for the remainder of the day.
Wool, synthetic, or blends are the best choice for cold weather socks.
And don't worry, wool used for hiking and work socks isn't the itchy variety. They're designed to keep your feet dry and comfortable for up to 16 hours per day.
Items to avoid
For general purpose urban wear, there's no need to wear athletic clothing.
Sure, these items are comfortable and functional, but much more stylish options won't leave you wanting in either of those departments.
That means ski gloves, running beanies, and Under Armor items are best reserved for winter sports.
Enjoy the season
Rather than thinking of winter as a period of time spent confined to the indoors, approach it like a challenge by donning a few simple cold weather accessories.
Use this as an opportunity to take Mother Nature head on and look awesome doing it.
Soon enough we'll be back to sweating through our t-shirts while standing under the shade tree and wishing it was cool enough to wear a coat.
All the best,