Winter menswear brings an elevated sense of texture, layering, and tone. I believe that the Fall and Winter months afford men the best opportunities to augment their style, and this article will describe what you can wear this Winter to stay cozy, comfortable, and stylish until Spring comes around.
1. BOOTS
Yes, boots are often as essential during the Winter as they are for the Fall (perhaps even more so). To keep things simple, everything I mentioned about boots in my Fall Wenswear article holds up a few months later; however, I want to reinforce the necessity of investing in a quality pair of boots.
2. WOOLEN SOCKS
It may seem silly to add this to the list as a standalone entry, but if you get a lot of wear from your boots out of necessity, here is my plug for why woolen socks are often better than cotton socks.
Woolen socks are antibacterial, so your feet will be better protected against infections and the stench that often precedes them. Additionally, wool traps the heat and keeps it closer to the skin, allowing for better insulation in frigid temperatures. Woolen socks also breathe better than cotton socks, and if you enjoy hiking, you'll quickly find that wool will allow your feet to stay dryer much longer.
On top of that, woolen socks are just less maintenance overall, thus (in my opinion) the superior all-around option for socks when paired with hardy service or work boots.
3. DARK DENIM
Dark denim jeans will stand the test of time, ensuring you look stylish for years.
Denim has cemented itself as a workhorse material in the fashion world, and it isn't going anywhere anytime soon. As I had previously professed for the autumn months, darker denim is typically the best and most versatile option for men during the Winter because the texture and tones harmonize well with all of the other entries on this list.
Dark wash indigo denim is always handsome and versatile, especially with various browns, greens, and charcoal tones/shades. Even black denim is surprisingly interchangeable and looks excellent during the colder months.
I believe that denim trucker jackets also have a place in the wintertime, despite not affording much extra warmth; however, if you're residing somewhere that doesn't get too cold, a nice sweater and a classic denim jacket will look excellent, provided it fits you well.
3. DARK CHINOS
As the most versatile pant option any man can have in his closet (you can quote me on that), chinos unquestionably belong in a Winter wardrobe. The various color options make the latter months unique for chinos: black, burgundy, dark olive, brown, navy, etc. Darker and often earthier chinos fit right in with the colder, often bleaker weather commensurate with the late-year lull.
4. FLANNEL
Flannel trousers and shirts can come in a variety of tones and patterns.
Flannel is a versatile and practical material that has become a staple in menswear for several years. Whether it's flannel shirts, trousers, or even suits, this material provides warmth and a lovely texture that compliments each of the other entries on this list. The softer flannel texture also provides a bit of visual intrigue that adds extra flair to most ensembles.
Just be sure not to go too crazy with the patterns. We want to dress elegantly, not overly "loud."
6. SWEATERS
This entry shouldn't come as much of a surprise. Sweaters are timeless, cozy, and comfortable ways to level up your style for the winter months. Chances are, you already have at least one or a few crew neck sweaters in your closet, but if you're looking to expand your collection, I recommend a few additional variations of sweaters.
TURTLENECKS
A well-fitting turtleneck is one of the most elegant things any man can wear, provided you make a point to keep in shape.
Turtlenecks are a great way to quickly elevate a classic two-piece layered look while lending the wearer extra warmth. If you don't own a turtleneck, you can't go wrong with a black, charcoal, or navy blue color. You will quickly find that these options can pair well with most items you probably already have in your closet.
CABLE-KNIT SWEATERS
I'll let you in on a little secret: rocking a chunky sweater, often in a cable-knit weave, is a surefire way to take your style game to the next level for Winter. There isn't much else that personifies coziness and elegance quite like a cable-knit sweater. When you combine a cable-knit sweater with other forms of outerwear, you'll be even more of a force to be reckoned with.
V-NECK SWEATERS
A v-neck sweater is like pairing Steven Spielberg and John Williams together; it just works. Few pieces lend themselves better to layering than v-neck sweaters, and if you've yet to acquire one, I recommend charcoal, gray, or navy blue. Throw on a crisp collared button-down shirt underneath with a classic outerwear piece, and you'll look smart for any occasion.
7. PUFFER JACKETS
Also known as the "down" jacket, a puffer jacket is an excellent example of doing more with less for the Winter. This piece looks particularly dapper when layered with sweaters. Still, you'll find that even with a classic oxford-cloth button-down (OCBD) shirt or standard polo, this piece keeps the wearer warm, insulated, and comfortable. Puffers rarely restrict movement and are incredibly lightweight, requiring little maintenance in the long run.
8. OVERCOATS
What can I say? Overcoats work so well during the Winter, and any man wondering if he can pull one off should stop questioning himself immediately. I can't tell you how many compliments I have received wearing my overcoats when the weather warrants one.
The color options of camel, gray, navy blue, or charcoal are nearly limitless in the combinations they can afford you; however, I would like to warn against purchasing a black overcoat as your first (or even second and third) one because much like suits, black is painfully overrated. Instead, consider opting for a charcoal overcoat, which goes well with black and many additional colors.
Camel overcoats are versatile and look brilliant with virtually any darker-toned color.
9. SCARVES
You can't go wrong with a classic charcoal scarf as your first one.
If you think wearing a scarf isn't stylish, think again! When the weather is cold, wearing a scarf lends you more warmth and can quickly elevate your layered look considerably. When acquiring your first scarf, I recommend keeping things simple. Any neutral-colored scarf in a solid pattern (gray or charcoal) will look excellent with any garments you layer underneath.
Even when wearing a scarf isn't essential, as long as the weather still merits one, using it as a style affectation will help you stand out. Just remember to always dress for the occasion!
10. GLOVES
Often reserved for the coldest climates, gloves are more practical than anything, but for any modern gentleman, a well-crafted pair of knit or even leather gloves can do wonders to bring your look together. Gloves can make you look much more sophisticated, especially with darker, monochromatic ensembles.
11. BEANIES (A.K.A. WATCH CAPS)
Beanies for civilians and watch caps for my military friends. Regardless of what you call them, they are often necessary for the Winter months (depending on where you live). I recommend snagging a few of these in various colors so you're covered for every situation or outfit combination. Great options for starting are charcoal, brown, navy blue, dark green, and burgundy.
WHAT ABOUT SNEAKERS?
Absolutely! If you're someone who lives in a place like Southern California, where it never snows along the coast and rarely ever rains (and thus the necessity for boots is pretty low), you can swap them out for a pair of sneakers and rest well in knowing that you'll still look great.
A great pair of white sneakers can easily compliment Winter wear such as coats and scarves!
