Whether you're snowboarding in the Alps or raking leaves in Wisconsin, dressing right will not only keep you comfortable, but up your winter style game as well.
This article will offer some tips and tricks for dressing for winter style. We cover Business, formal, and casual style for men.
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When is Winter?
Great question. Much like our summer style article, we'll begin with the question of when "Winter" actually is. In the Northern Hemisphere, Winter begins on December 21st and ends around March 19th.
With that out of the way, let's do a quick breakdown of the best fabrics to stay warm in cool weather.

Fabrics to Stay Warm in Cool Weather

Wool is the first fiber many of us reach for in cool weather, and with good reason. It's a dense and insulating material. It is also quite breathable- which means we don't overheat. That's extremely important, even in winter!

Cotton is the second material we think of. It's readily available, often inexpensive, and will do the job of keeping you warm, especially in a dense knit. However, cotton holds on to moisture and doesn't breathe nearly as well as wool.
This moisture retention can cause quite a bit of discomfort and temperature swings- especially if you sweat. No one likes cold sweat clinging to them shoveling snow in the middle of January!

Cashmere is often-incorrectly- thought of as being a type of wool. It's actually the undercoat of Cashmere and Pashmina goats.
The largest producers of Cashmere are China, Mongolia, and other Asian countries, although the West has attempted to replicate the process with limited success.
Cashmere is especially soft and quite delicate. It's also fairly difficult to acquire, which often makes it extremely costly.
Raw Cashmere
Raw Cashmere is soft and fibrous!
However, it can be woven into socks, hats, glove linings- even overcoats! Mostly commonly, though, you'll find it in sweaters.

Polyesters and Synthetics
While we at Ask Andy usually encourage natural materials (like the above) whenever possible, manmade materials do have their place in a man's winter wardrobe.
Because they're hydrophobic, they repel moisture and keep the elements away from your body. They're also an insulator and trap heat. This also means, though, these materials don't breathe very well.
Even with that in mind, these materials still have their place in a man's winter wardrobe. They're hydrophobic, meaning they repel water very well. This makes them ideal for ski jackets, parkas, and other garment designed for winter sport.

Winter Style for the Office

Business Formal

Business Formal Suiting
In cold weather business formal, suiting is very much your friend.
For cloth, something in the 12-14oz range would be best. It's substantial, but not so heavy it becomes uncomfortable to wear.
Weaves in pure worsted wool are affordable and versatile. Merino wool is often used as well, but we find it better suited to sweaters.
The same goes for cashmere. While you can find suits in cashmere blends and even pure cashmere, the resulting garment is often so delicate you can't get more than a few uses out of it per year. And, what are good are clothes if you can't wear them?!
In this day and age, even in a business formal environment, a gentleman of style can wear a flannel suit. Not to be confused with lumberjacks or hipsters, this version of the cloth is defined by the milling process in which the wool is not combed and pressed, but instead left rather fuzzy and soft.
Brian Sacawa from He Spoke Style in a Grey Flannel suit
This results in a pleasing and interesting texture. However, bear in mind flannels tend to lose their crease and may require frequent pressing.

Business Formal Shirting
While open-weave poplin is de rigueur for most of today's business shirts, their light and airy texture won't stand up to winter's icy blast. Consider, then, investing in heavier, closer-knit twill shirts.
Twill fiber
The diagonal lines of Twill fabric
That weave (seen above) creates a unique diagonal pattern that reveals its intricacies only upon close inspection.
As for shirting styles, twill tends to work best in solid applications. However, you can get away with a thicker Bengal or London stripe if you prefer- a butcher or awning stripe only really works with breezy poplin.
Colors of white and light blue should be the foundation of your wardrobe.

Business Casual

Blazers and Sports Jackets
We encourage the well-dressed to add a jacket whenever possible, even in the grey area of "business casual."
A solid, navy blazer will always serve you well. Single or double-breasted is really up you.
Jackets with pattern are also especially at home in the business casual arena. Consider Windowpane, herringbone, puppytooth, or glen check in a tasteful size, and you'll be in great shape.

As for cloth, both worsted and flannel are excellent choices for business casual. Tweed is becoming more accepted today, but we'd still exercise some caution here- the fabric was originally used for stomping through marshes while on a hunt!

Sweaters and Sweater Vests
Winter style works best with layers, and sweaters or vests are a great way to add depth and visual interest to your outfits.
Fabrics in cashmere, 100% merino wool, and cotton all work well.
For sweater style, you'll usually see one of four styles: a v-neck, a crew neck, turtleneck, or cardigan.
A v-neck is, of course, characterized by the "V" shape cut into the neck. Functionally, this allows for easily putting on or removing of the garment.

Aesthetically, it shows a little more of your neck or a well-built upper body. Stylistically, it allows you to display a necktie- and this is what style we'd recommend should you choose to have neckwear.

A crew neck is cut more closely to the neckline. Use it sparingly in the office, though, as it looks kind of odd with a collared shirt underneath.
Turtleneck for Winter

A turtleneck can take the place of neckwear in a business casual environment. It's gone in and out of style over the decades, but we believe a thin, merino wool or cashmere turtleneck can be a very rakish winter style look.
A cardigan can be nice to keep at your desk. It's got a button front, which means you can put it on and take it off more easily and without mussing your hair before the next meeting.
As for sweater vests, they may be best suited to the more traditional and seasoned gentlemen among us.

Business Casual Shirting
Like with business formal, heavier weight cottons are also your friend here. Again, twill may not play as well with pattern. But, in a business casual environment, consider tattersall, gingham in muted colors, and stripes.
Here, you can also include an Oxford Cloth Button Down. This quintessentially trad item in a heavy weave is perfectly acceptable in a business casual office.
Love Trad clothing? Join us in Trad Style where we discuss all things Trad related!
- Andy & Mike
Consider collars with a substantial "roll" to them and in light to medium blue.
Ratio Clothing Oxford Shirt

Looking for a brand? Check out our Andy's Favorite Brands page for our favorite shirt makers!

A charcoal to mid-grey pair of flannel trousers will always serve you well in business casual. We'd encourage you to invest in the best you can afford.
Navy and brown are classic choices as well.
If you choose to skip the jacket, you can have a little more fun with your "odd" trousers. As with the jacket, houndstooth, herringbone, and Glen check can work beautifully. The check in the latter can be any color you wish- cream, pale orange, or even a light pink can look particularly smart if done tastefully.
Of course, do make sure you're not wearing the same pattern as your jacket, should you choose to add one!

Winter Style Business Accessories

For socks, we'd recommend models in merino wool. It's flexible and warm, but still quite breathable. This can be useful if you tend to overheat.
We'd also recommend investing in over-the-calf socks. These will not only keep your legs warm, but will result in cleaner, smooth lines from you shoes up your leg line. Besides, no one wants to see hairy calves!

Undershirts are a matter of personal preference for the well-dressed. We're okay with them here at Ask Andy, though. They absorb sweat in summer and are an extra, insulated layer in the winter. Here are a few considerations when wearing an undershirt.
Opt for a V-Neck.
Too often, men go for thick, cotton shirts with crew neck collars. This looks sloppy when going tieless.
Fabric Matters.
Cotton is standard and will do just fine. However, you can also consider TENCEL, MicroModal, Silk, Nylon, or the super-insulating (and expensive!) -but potentially itchy -- Merino Wool. Looking for a wool alternative? Check out undershirts made from acrylic yarns.
Stick with Short Sleeves.
It can be tempting to choose a long-sleeved undershirt in the cool weather, but we'd advise against that. It's very hard to roll your sleeves up! And, it's easy to overheat. Short sleeves are still your best option here.
If you're considering winter undershirts, we'd recommend this guide here.

Winter Style for the Weekend
As much as we at Ask Andy love our suiting, there is a time and place for casual attire.

For weekend shirting, flannel is a go-to for many of us. We'd recommend a heavy weight cotton.
Flannel Shirt Winter Style

Flannel, of course, comes in a variety of patterns, but Black Watch plaid and Buffalo check are some of our favorites.
Oxford Cloth Button-Downs (OCBD) are also a wonderful piece of weekend wear.

Sweaters & Sweatshirts

Much like with business and business casual, V-Neck, Crew, and Turtleneck sweaters all work well in casual settings.
A V-neck over an OCBD and worn with some dark denim is a failsafe option for evening get-together at a friend's house.
A turtleneck, though, can make for a fun layering option- especially if it's a thinner one.
Denim jacket winter style

Consider pairing with a denim jacket and a topcoat, as we have here!
Looking to learn more about winter coats? Be sure to check out our comprehensive Men's Winter Coat Guide article.

Sweatshirts are a trickier option for the classically-styled gentlemen, as they were, of course, originally gymwear. Today, they're most often oversized, with floppy hoods and large sports team or brand logos splashed across the chest. We'd certain not advocate that out in public!
However, fitted, hoodless options in navy, oatmeal, medium grey, or olive (the best colors for men!) are excellent options for you.
Consider pairing this type of sweatshirt with dark or light wash denim, corduroy or twill pants, or heavyweight chinos.

Casual pants are another broad category of men's winter style. We'll try to give a brief overview below.

Denim is, of course, the most ubiquitous of casual pants these days. It comes in a wide variety of weights, and we'd certainly recommend a heavier weight for winter.
How heavy? Anything from 14 to 17oz should be more than sufficient for winter wear-although denim can get well above 20oz!
Most of the heavy denim is raw - meaning unwashed. If you'd like to learn more about raw denim, you can check out this raw denim community discussion here.
However, denim does tend to retain moisture, so if you're doing heavy physical activity, shoveling snow, or things of that nature-we'd avoid wearing it!

Corduroy is a cotton fabric with a tufted, vertical pattern, or 'cord.'
The vertical channels trap heat within, keeping the wearer warm and insulated.

Originally a working-class fabric in the 19th century, it was adopted by the trad and prep students of the 1960s and even made its way in the grunge scene of the 1990's.
Today, it's the perfect pairing to a flannel shirt, but you can also find even causal suits made from it!

Not derived, of course, from subterranean mammals, moleskin is a heavy, but soft, cotton fabric is that is woven and then sheared to create a nappy, brushed finish.
Moleskin Fabric

While it has applications beyond clothing (medical devices and microphone covers), it plays very well for winter style for men. Consider a pair of pants in brown, navy, or even emerald green or burgundy!

Boots and Shoes
Proper footwear is essential for winter style and comfort. We'll give a brief overview below- a deep dive requires it's own piece!

Boots for Winter Style
We'd recommend five boots for the well-dressed gentleman
  • Brown Leather Wingtip Dress Boot
  • Brown Leather Chukka Boot
  • Burgundy Cap toe boot with a Rubber Sole
  • Black Sleek Chelsea Boot
  • Rubber "Duck" or Snow boot
We'd recommend your boots come with a six-inch upper to keep out rain, snow, and sleet.

The rules for shoes follow the same as summer. Oxfords, derbies, and the like are always in style!
Loafers can be okay, but consider only breaking them out on the cooler days without snow and ice in the forecast.
Dainite Sole

For added traction, we also recommend considering models with Dainite rubber soles or with a double sole.

A Final Note on Winter Style: Protect Your Face!
A gentleman is more than the clothes he wears. Skin protection is paramount. Consider a moisturizer for your face, and do remember petroleum jelly to prevent or heal chapped lips.
Sunglasses have use all year round. Reflections from snow, icicles, and and ponds can damage your eyes.
And, of course, this is only a guide and not intended to be all-inclusive.
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If you're looking for more winter style inspiration, consider any of our community discussions on:
Thanks for reading, and stay warm and dry!