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10 Winter Essentials to Upgrade Your Style

January 18th, 2022

Winter Must-Haves & Style Upgrades

This is not going to be just another run of the mill men’s winter essentials post. Because instead of just telling you that you need a coat, a scarf, and a hat–who doesn’t know that, right?–I’m going to be doing three things a little differently.

First, I’m going to get very specific with my recommendations.

Second, I’m going to tell you why I think these items are the things that you really need.

And third, I’ll go a little beyond the usual than some of the items you typically see in these types of roundups.

Let’s get started.

Top 10 Men’s Winter Essentials

1. Grey Flannel Suit

winter essentials men 2022

Winter essential number one is a grey flannel suit. It’s very important to have a suit that matches the season and if you’re only going to have just one, I recommend that it is a grey flannel suit.

Flannel is one of the best and most classic winter fabrics–it helps keep you warmer. And the grey color is very versatile so you can pair it with a wide variety of shirt and tie combinations.

But the best part about a grey flannel suit is that not only are you getting a full suit, but you are also getting a great stand alone jacket and a great standalone pair of pants, which expands the options that you have in your wardrobe exponentially.

And that is why a grey flannel suit is my number one winter essential.

2. Cashmere Sweater

cashmere sweater men's winter essential

Winter essential number two is a cashmere sweater. Like flannel, cashmere is a great fabric for the winter season. It’s very soft, it’s very warm, and a cashmere sweater is a garment that is instantly going to upgrade your winter style.

In terms of types or styles of cashmere sweaters, the one you choose kind of depends on what you’re going for.

A crew neck is a great casual or more laid back option. You could wear it by itself or easily layer it over a button-up shirt for a very simple and classic look.

Or you could go with a turtleneck for something a little more elegant and sophisticated.

Cashmere is always going to be a little pricier, but there are companies like Gobi Cashmere and Falconeri, for example, that do offer less expensive direct to consumer pricing.

With a cashmere sweater you are getting tons of style, sophistication, and a touch of luxury. And that is why it is one of my winter essentials.

3. Cozy Robe

Winter essential number three is a cozy robe.

It’s cold outside, which means it’s going to be a little colder inside as well, especially when you first wake up in the morning, so having a nice robe to throw on as an extra layer is not only practical in the sense that it helps keep you warm, but it’s stylish as well.

During the wintertime, I think it’s great to have a robe in a seasonal pattern, like a tartan plaid. I recommend checking out L.L. Bean because they have some great options, and they’re also very reasonable in terms of price.

Now, if you’re looking for something a little more “sartorial”, you might opt for what’s called a dressing gown. A dressing gown is meant to be worn over clothing so it should not be confused with a bathrobe.

In addition to being more elegant than regular robes, dressing gowns are generally more expensive than regular robes, but if you invest in one, they are nice to wear around the house this time of year.

And if you get a really fancy one, it’s a great way to make an elegant statement at a holiday party or winter cocktail party that you might host.

4. Leather Gloves

Winter essential number four is a stylish pair of leather gloves.

Typically when guys go to buy a pair of leather gloves, they’re going to go for either a black or brown pair–and that’s fine, I recommend that as well. But the style of the glove is often very simple because the simpler the style, the more versatile it’s going to be, right?

Not necessarily.

Take a look at this pair right here. It has a very intricate and unique woven back, which is such a cool standout detail, but it’s subtle enough–especially from a distance–that it doesn’t take away from your ability to style them many different ways.

For a more casual pair, you might consider something like this. These are made from genuine shearling leather with a warm wool inside and a suede finish outside. If you have a more casual, maybe rugged or outdoorsy style, I think these would be a great pair of gloves for you.

5. Dinner Jacket / Smoking Jacket

Winter essential number five is a dinner jacket and/or a smoking jacket.

Around the holidays, although they’ve passed now, it’s always a great time to dress up more formally. Typically, when wearing formalwear, I would recommend keeping it pretty simple and not calling attention to yourself.

But during the wintertime, and especially during the holidays, it’s always nice to have a little more fun and be a little more festive, isn’t it?

There are two ways I like to do that. And the first is with color.

Burgundy is a great color for a dinner jacket. It’s perfect for the holidays, perfect for the wintertime, and it’s definitely something that you could wear for other formal occasions throughout the year.

Second, is to choose a velvet fabric and opt for a slightly more eccentric smoking jacket style. Here, I’ve got on a double-breasted, shawl lapel version with great piping details around the button closures, on the sleeves, and on the edge of the lapel.

6. Silk Scarf

Winter essential number six is a silk scarf.

A silk scarf is a great elegant alternative to a wool scarf or a cashmere scarf. The fabric is much thinner than wool or cashmere so you have a lot more options in terms of how you can tie it and how you can style it.

For example, you can easily wear it practically for warmth under your coat, but it also makes for a really elegant accent with a suit or tuxedo.

Personally, I love a silk scarf with a simple polka dot pattern because it’s just so classic and timeless. Navy is a great choice for the most versatility. Black, if you plan to wear it more with your formalwear. And burgundy is always a great choice for the holiday season.

7. Casual Warm Coat

Winter essential number seven is a casual warm coat.

Even though we’ve been talking about mostly “next level” style items, I do think it’s important to have a really good casual coat also. In other words, a coat that’s not an overcoat.

Obviously, we want one in a thick, warm fabric. And my pick for the best casual yet very stylish winter coat is the venerable peacoat.

The most classic version of this is the navy peacoat, which is extremely versatile. But if you’re interested in something classic that’s a little different, I would choose something in a brown tone. It’s just as versatile as navy, but quite unexpected and very stylish.

8. All-Weather Footwear

Winter essential number eight is some all-weather footwear.

Now you might think, based on my selections so far, that I’m going to say that you need to get a pair of Hunter boots. But that is not the case.

I mean, don’t get me wrong, Hunter boots look great in all the idyllic heritage brand men walking together in the their best tweed through the hillsides and mud in Scotland photos, but that’s not reality and I’ve come to the realization that as much as I might want that l want to pretend that that is my life, it’s not, so it’s not practical.

What is practical, however, is what is my favorite pair of all weather footwear–the never out of style Bean Boot from L.L. Bean.

I actually have three pairs. I have the Mocs. The Gumshoes. And I have the 8” boots.

Between those three I’m covered whether I’ve just got to run out to let the dog do her business, split and gather some firewood from the backyard, or shovel several inches of snow from the driveway.

You could even pick up a flannel-lined pair for some added warmth.

9. House Slippers

Moving from utility to luxury, we have winter essential number nine–a pair of house slippers.

And I’m not talking about your regular old clunky slippers. No. Here, we are talking about a more classic, sleek, and old-school style of slipper.

These types of slippers–or house shoes–look and feel much more refined, and that is why they are one of my winter essentials

10. Statement Overcoat

One of the great ways to stand out from the crowd during any season, is to have a unique version of a garment that everyone is wearing. Which is why winter essential number 10 is a statement overcoat.

The first thing that stands out, obviously, is the pattern. It’s a big and bold houndstooth check. Patterns like this are great during the winter because they provide a big contrast to what is typically a more minimal and bleak landscape.

It’s made from a thick wool and also has a quilted inner lining–so it’s a very warm coat.

And it has a few more subtle details that help make it even more unique and special, like the Prussian collar, raglan sleeves, hidden button closures that go all the way up to the neck, and sleeve tabs.

Chime in: What do you think of these winter essentials?

Stylishly Yours,

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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