Men’s Winter Hats – The 5 Best Men’s Winter Hats to Buy Right Now

Nothing pays more dividends in the menswear world (and indeed, in life) than the art of preparation, and that’s why we’re recommending you start diving into the world of men’s winter hats right now. It might be the middle of summer (where we are, at least), but getting ahead of the game is as crucial as ever. And although it’s mighty tempting to stick your head in the sand and hit the coast, spare us a few moments before you hit the road to the beach. Think ahead, if briefly, to the depths of winter.

Be grateful for the chance to get away this summer, sure, but know that you can rest a little easier if you’ve already started stocking up on the best men’s winter hats (because you do need more than one). Think of it like investing in your future self, or at least, investing in your future wardrobe before you even need to do so. Again, remember what we said about dividends?

Men’s winter hat options abound, with both luxury options and hard-wearing, rugged winter hats up for grabs.

When that first snowfall hits, when the first flakes on the edge of a blizzard roll into town, you’ll already be well-stocked. There’s also no time quite like the present to do even more additional planning. Take, for instance, the art of searching for one of the best men’s peacoats or stocking up on the best leather dress boots. Those are just two of the right style moves to make come fall and winter, but it’s all for naught if you can’t keep your noggin warm with one of the finest men’s winter hats out there.

There are options aplenty out there, from heritage brands and from companies that are a bit newer to making men’s winter hats. You’ll find reliable pieces best worn out in the field when hiking or camping, and you’re also bound to come across hats that are best paired with cardigans and chambray shirts for more casual wearing occasions. The coolest winter hats even straddle the line a bit between the two (for instance, the Filson Watch Cap we’ll talk about works with a thermal base layer and a flannel shirt for grabbing a pint, and it also wears easily on outdoor getaways and weekend strolls). You can make anything your own — or just about anything — in the winter wonderland of men’s headwear.

One added incentive to doing a little bit of advanced planning? You’ll find discounts aplenty right now on the best of last season’s gear. And for the trained shopper, it can also be a bit of a primer: Brands are due to start releasing their fall collections in just a few weeks’ time, and there very well might be one of your new favorite men’s winter hats in that assortment, too. If you just can’t wait to pull the trigger as you dream of a reprieve from the mania that is a summer heat wave, you’re in luck.

It might even serve as some winter style inspiration to start shopping right now. Think of it like planning out your own Pinterest board of sorts, starting from the top-down (or mixing and matching your favorite winter style staples). After all, the right winter hat can add a pop of color — a la Bill Murray’s red wayfarer cap on the silver screen — or it can simply protect you from the elements (see: Any film involving Liam Neeson). You’ve got choices, and that’s a great thing.

Men’s winter hat options abound, with both luxury options and hard-wearing, rugged winter hats up for grabs. If you know where to look and what to shop for, you won’t come up empty-handed (and your head and ears will stay a heck of a lot warmer when temperatures really start to plummet). First, a few tips on finding the best winter hat for you.

How to Shop for a Winter Hat Right Now

  • Think boldly: What does being bold have to do with shopping for a winter hat? Well, more than you might think. Right now, brands are looking to offload remaining winter hats as they make way for new and ever-more-stylish inventory. That means you can find unexpected deals and top-notch quality on the coolest men’s winter hats, especially from brands that might be a bit pricier the rest of the year. It also means quality fabrics and neat patterns are also well within your reach, and again, this is true even of brands that might not normally be all that accessible. So go on: Think boldly and search out a new frontier with the warmest winter hat around.
  • Dress for the occasion: Just as there are different types of, say, combat boots to help you tackle fall and winter, there are different types of winter hats out there, as well. Some winter hats are made with a thick and close-weave, textured knit from heavy wool, all the better to provide maximum insulation in frigid temperatures. Other winter hats are woven from luxurious materials like cashmere, which is like a hug for your cold ears when it gets blustery. Winter hats made from more fine materials, like cashmere, are a reliable way to top off your ensemble if things tend to go a bit dressier (say, if you’re wearing a camel topcoat, slim blue jeans and dress boots). Consider adding both to your rotation.
  • Keep it simple: Way back in the day, as a young fella, perhaps you wore a winter hat with a zany pattern or some added bells and whistles (ear flaps and tassels, anyone?). We’re here to say that these days, it’s best to keep your winter hat mostly unadorned and more straightforward than wild. That means mostly solid colors and stripes are welcome, but overly loud and garish patterns aren’t all that favorable if you want a stylish winter hat. By all means though, if you need to wear a neon winter hat on the job site, go for it — seriously. But off-duty, opt for something a bit more stylish, rugged and functional — for instance, a classic, solid winter hat never let anyone down, not even Daniel Craig.

Now that you have a better idea of what to shop for as you search for men’s winter hatsa, let’s dive into the real business of today: Our favorite winter hats to buy now. These won’t be around for long, so shop accordingly.

Our Favorite Hats to Buy Right Now

Filson Watch Cap Beanie

Filson Watch Cap Beanie

If ever there were a brand to count on when it comes to rugged winter gear, it’s Filson. We love the Pacific Northwest retailer’s penchant for outfitting those in all walks of life, from rough-and-tumble explorers to those who are more comfortable exploring a Brooklyn taproom (guilty as charged). The Filson Watch Cap Beanie is versatile enough to do both, made from a thick knit in some versatile colorways. The fact that it’s crafted from USA-sourced wool is an added bonus.

Mack Weldon Tech Cashmere Hat

Mack Weldon Tech Cashmere Hat

On the other end of the spectrum from the more rugged Filson Watch Cap Beanie sits this super-soft, sleek Mack Weldon Cashmere Hat. It’s designed for the guy on the go, and ideally, one who layers his Mack Weldon Oxford shirt underneath a Mack Weldon cashmere sweater (each of these pieces are worth looking into on their own, for what it’s worth). This cashmere hat is sleek enough to act as a stylish hat alongside tailored ensembles, but you can also wear it on early morning runs when the thermostat plummets.

Huckberry Beanie

Huckberry Beanie

Don’t want to break the bank right now when shopping for a winter hat? Well, we noted above that you’d find some standout deals on winter hats, and this is one of them. It’s produced and designed by the team behind excellent and hard-working retailer Huckberry, which means that you can count on the quality, the versatility and the price. There aren’t all that many color options left at the moment, but it’s sure to be restocked as we roll into fall and winter. Get ahead of the game and pick it up right now.

Lands’ End Rib Knit Beanie

Lands’ End Rib Knit Beanie

Here’s another fine example of a hat that’s worth picking up right now, although you might be more interested in Lands’ End summer gear. The Rib Knit Beanie, a straightforward classic available in an array of colors, is available for under $20, and is an utterly classic winter that’s quite well-made. It’s what you should expect, after all, from a retailer that knows how to outfit hard-working men and women through coastal storms and sunny days alike.

RoToTo Bulky Watch Cap in Black

RoToTo Bulky Watch Cap in Black

As stocked and sold by menswear design luminary Todd Snyder, this durable and thick watch cap fits within the best of both worlds. Warm enough to wear on a winter hike, cool enough to wear downtown at that hip cocktail bar. The versatile black colorway is a cool-kid move when you wear it alongside a navy peacoat and slim blue denim, kind of like our man Mr. Daniel Craig might do. And while you shop for your new favorite winter hat at Todd Snyder, you can get a few new pieces from the brand to complement your forthcoming winter style mood board. Preparation makes perfect, you see?

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Beau is Brooklyn-based style and lifestyle writer. He covers menswear, gear, spirits, craft beer and music. When not writing, Beau can be found shopping for vinyl or sipping on a Brooklyn beer.

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