Baby, It’s Cold Outside. Dress for It.

Winter is a pain in the ass. Whenever you go somewhere, it involves putting on layers, then taking them off, then doing it all over again when you go back home or to the office. And when you go to a restaurant that doesn’t have coat check, all the coats, scarves, hats, gloves and other bulky winter gear takes up space around the table. Then there’s losing gloves, scarves or hats, often in a taxi. I’ll say it again: it’s a pain in the ass.

The alternative to this ass pain is to white knuckle it and wear wispy layers like thin a thin jacket or just a scarf or gloves. Hats are the trickiest, since they mess with our vanity. The young ones among us are bigger fans of this route. In my experience, white-knuckling the cold for the sake of vanity isn’t worth it. For ages, I put off getting a proper topcoat and puffer jacket until I caved and snagged the good ones I’ve had for years. Nowadays, I’m amused by guys who unnecessarily suffer low temperatures out of vanity or a perceived notion of saving a hassle. These guys always seem to be the ones with runny noses or colds.

The good news is that dressing for the cold need not be a sacrifice of aesthetics. In fact, guys properly and handsomely dressed for the weather probably look a bit smarter than guys who don’t. Below are some tips and observations as well as some of my own tricks with my winter kit.

Topcoats and Overcoats

Many men think of topcoats as overcoats, which are not necessarily interchangeable by definition. They are both “over” coats that are typically worn over suits, but can just as well be worn in casual situations over jackets, shirts and jeans. Topcoats are typically lighter in weight and fall above the knee in length. Overcoats are usually made of heavier wool or cashmere and fall below the knee. I don’t own a full-blown overcoat, since I don’t really spend enough time outdoors between buildings to warrant such a heavy coat. I have a topcoat, which seems to do the trick, particularly in terms of length when riding my bicycle.

A common mistake many men make with the topcoat or overcoat is same as the common mistake made in suits: the fit. American men tend to go too large, thinking a bigger chest/shoulder makes them look more formidable, when in fact it has the opposite effect. It’s like the hairpiece illusion: we can tell. When you’re not big enough to fill that jacket or coat, you’re not fooling anyone. For all jackets and coats, go snug in the shoulder. For overcoats and topcoats, there is a myth that one should go one size up from their suit. Not true. Presuming your jacket is the right fit, choose a topcoat or overcoat in the same size, not one larger. Off the rack, I’m close to a 38R. My topcoat is also a 38.

Scarves

For real warmth with a scarf, you want wool, cashmere or a blend thereof. The numeric measurement of a good length and width of a scarf is like porn to me. I know it when I see it, in the same way that I can tell between good cartoonporno videos and ones that aren’t worth my time.

My favorite way to wear it is by folding it in half lengthwise, throwing it over my neck so both ends hang over my chest, then slipping the double end through the folded end, essentially creating a casual knot around my neck. Another simple way is to just tie it in a simple knot in the front. Just as long as it doesn’t look too affected or like you’re trying too hard. I wear scarves out of necessity, not adornment. That said, the necessity must be met with a simple sense of style.

As far as color and pattern, my scarves are like my ties. Simple and understated; nothing too loud or “conversational.” I like something that goes well with my coat, and something that complements my suits and jackets well in the (warmer) event I wear just a scarf with no coat. Over the years, I’ve bought, loved and lost many. Currently, I own two scarves. One is a solid, dark olive green wool cable knit scarf that resembles an extra long sleeve of a sweater. My other is charcoal with tan, dark blue and light blue stripes on it. It goes well with much more than I anticipated when I bought it years ago.

The only tricky thing about scarves for me is stubble. Wool and cashmere scarves get snagged on my beard if I haven’t shaved, sometimes causing the scarf to pill off onto my whiskers. Scarves, for me, are best enjoyed with a clean shave or a full beard.

Gloves

These are a no-brainer for me. The simpler, the better.

My current pair is the classic pair of black gloves made with buttery soft leather and a nice cashmere lining. No straps, no snaps. They go with everything. If I had the budget or the desire, I’d get them in other colors, too, but I’m just not that breed of cat.

Hats

A lot of guys hate hats. I get it. They mess with our hair and, subsequently, our vanity. But when it’s 16°F outside, I kinda don’t care. Thankfully, there are some fun faux fur* options of which I’ve taken advantage. I’m personally partial to trapper hats, and I have two of them: one full gray faux, and another with a camouflage shell and a faux fur lining. My third and only other hat is the classic black, ribbed wool cap. Where and how I rotate my hats depends on what I’m wearing at the time, how I’m feeling, where I’m going and how cold it is outside.

Puffers and Vests

As I said earlier, I put this one off for years. Like an idiot, I braved the cold miserably in insufficient outerwear, for what reason I really can’t recall. The cold would always catch up with me, causing me to practically mainline Theraflu and Emergen-C. I finally found a jacket I liked. Dark navy with a snug fit, ample pockets and a detachable faux fur-trimmed hood. I’ve had it for about six years, and it saves my hide every winter, especially when walking the dog in extreme cold. I also have a simple, black, down-filled vest, which also comes in handy on its own or as an extra layer.

As I see it, these jackets and vests are for casual only – with jeans, chinos, cargos or other casual fare. I often see images in magazines where fashion editors try to push this look in which guys wear a down vest or puffer over a suit. I can’t.

The Pea Coat

I’m a sucker for these. A well-made, fitted pea coat delivers a classic, structured and decidedly masculine silhouette. A good one fits in the shoulders like your suits and jackets, and it hugs the form well. A genuine pea coat is made with a densely woven, heavy 100% wool shell in dark navy or black and adorned with six anchor buttons.

In the late ’90s, I was lucky to find an original, perfectly-fitting (38), Navy-issue pea coat at a flea market. It belonged to an actual seaman named Charles “Charlie” Way, service number 492-98-21. After a little research online at navylog.org, I found the record of a Charles Way from Enola, PA (born January 19, 1940) who served from June of 1958 to June of 1960.

Mr. Way, if you’re reading… I have your 55 year old pea coat. Over the years, some buttons have come off (all original and saved) and some seams have come out, but I’ve had them all repaired. The coat is in great shape, well taken care-of and worn proudly. If you ever want it back, let me know.

And so…

That’s the story of the winter kit for this city dweller. There are surely other solutions that work well for many guys, but in terms of form and function, this is what has worked very well for me for many years.

* A word about fur… We’ve come a long way since living in caves. We don’t need animal fur to make a coat, an accessory or a vulgar statement that projects prestige. As a proud friend to animals, I do not now and nor will I ever endorse real fur. The fur industry is a soulless and inhumane (and inhuman) industry that should be burned to the ground.