The 6 Best Winter Jackets (That are Actually Stylish)

We all know there are endless options for stylish fall outerwear — waxed trucker jackets, Harrington jackets, field jackets — but once the temperature drops below freezing, it’s tough to find something that’s not a boring puffer or bulky, over-engineered ski parka.

After more than seven years of writing about casual, durable menswear while braving New York City winters — as an Australian transplant who really feels the cold, mind you — I’ve done a lot of outerwear experimentation and decided I’ve found the six best winter jackets that meet my criteria: long-lasting, warm, stylish, and with a certain cultural merit. (I’ll explain as we go through the picks.)

If you want a warm winter jacket (OK, a couple of these are coats) that actually looks good and will last a lifetime, we’ve not only got you covered (literally, har har) but I’ve also made sure they’re each a different style of jacket. For each category I’ll name the best option and then one or two cheaper alternatives that are still pretty dang good.

I can promise that all of these are warm enough for New York winters but just to make sure those snooty Canadians can’t tell me these are too weak for their Yukon snowstorms, I’ve even included one that’s worn by Antarctic researchers.

My Top Picks for Best Winter Jackets

• Warmest Leather Jacket: The B3 Jacket
• Warmest Casual Jacket: The N-1 Deck Jacket
• Best Wool Coat: Filson Mackinaw Cruiser
• Warmest Denim Jacket: Freenote RJ2
• Warmest Jacket of All Time: Canada Goose Expedition Parka
• Best Pea Coat: US Navy Peacoat

Warmest Leather Jacket: The B3 Jacket

• Popular with fighter pilots in World War 2.
• Made from shearling, offering incredible warmth in extreme cold.
• Available in a range of models.

Originally designed for Royal Air Force pilots braving 25,000-foot altitudes in uninsulated cockpits, the B3 jacket is almost totally made of shearling — made by tanning sheepskin with the wool still attached — making it exceptionally warm.

Ideal for anyone challenging the chilly climes of a Yukon Christmas, the B3 was famously worn by Rocky Balboa during his cold-weather training in the USSR.

There have been many versions of the B3 jacket throughout both military history and the history of civilian fashion brands being inspired by it, but we’re highlighting a replica of Mr. Balboa’s that will make you feel like you can beat up a roided out Soviet, seemingly convince the politburo to give up communism, suffer brain damage that forces you into retirement, and then 15 years later come out of retirement because I guess you weren’t that brain damaged after all.

Below is the link for the version Rocky himself donned, but if your heart is after another variation, give these a look.

What We Love:

• Heritage Rich: The B3 boasts a prestigious history, having been worn by RAF pilots during WWII.
• Warmth: Thick, shearling lining insulates and handles cold weather as well as high altitudes. It’s far and away the warmest way to wear a leather jacket.

What to Consider:

• Bulkiness: Between the thick wool and thick leather beneath it, it’s a bulky jacket.
• Price: High-quality shearling is expensive, especially when it makes up as much of a jacket as a B-3 does.

Cheaper Alternative

For those on a budget, consider the Bronco jacket by Thursday Boot Company. It’s got the warmth of an all-shearling jacket but a more modern aesthetic and more accessible price point.

Best Casual Winter Jacket: The N1 Deck Jacket:

• Originally designed for the U.S. Navy during WWII, built for harsh conditions.
• Made from a dense cotton “jungle cloth” shell for toughness and easy upkeep.
• Traditionally lined with alpaca wool for superior warmth.
• Great casual aesthetic that doesn’t look too vintage or dressy.
• Our pick has a lifetime warranty for repairs.

The N1 deck jacket is my personal favorite winter jacket.

This piece was built for the U.S. Navy in World War II when they had work to do and couldn’t wear their more formal, less expendable, less roomy, and harder to launder peacoats. (More on those later.)

Designed to withstand extreme weather on the high seas, the N1 has a cotton shell made with a textile you’ve likely never encountered: jungle cloth, sometimes called Bedford cord or whipcord, is an extremely dense kind of cotton that withstands all manner of wear and tear.

Traditionally, the deck jacket was lined with alpaca wool, which was used because the nation was running low on sheepswool during the war and found this as an alternative. Fortunately, due to the fibers having more hollow space to hold warm air, it’s said that alpaca turned out to have a greater thermal capacity than even sheepswool.

Many brands have tried their hand at perfecting the deck jacket but for our money, Iron Heart’s deserves its status as the best: relative to replicas (like the Buzz Rickson’s I also owned), Iron Heart’s is less itchy, better fitting, and has more functional pockets. Plus it comes in a range of colors!

What We Love:

• Durability: The hardwearing jungle cloth takes a beating.
• Classic Style: It’s casual but doesn’t look sloppy; a great piece to throw over a t-shirt.
• Heritage: Not only from the military history, deck jackets were also worn by James Dean, Paul Newman, and Chris Hemsworth in Extraction 2.

What to Consider:

• Fit: Modern versions, like Iron Heart’s, have a more tailored fit. If you get a reproduction, expect something boxy.
• Closure system: The first thing that drew our eyes was the way you zip up the jacket and then close buttons over it. It’s more water resistant this way and was designed to keep zippers from jamming with frozen saltwater, but it can be time consuming to close this jacket. Especially with gloves.
• Pretty darn casual: I have trouble wearing mine with a button up, unless it’s a flannel.

Cheaper Alternative

Triple Aught Design offers a budget-friendly version under $400, maintaining the authentic jungle cloth shell with a synthetic lining for cost efficiency. Polyester’s still pretty warm, and it’s a good price for made-in-UK.

Best Wool Coat: Filson Mackinaw Cruiser

• Made from nothing but 24-ounce heavy-duty wool for exceptional warmth and durability.
• Unlined, so it’s breathable and comfortable across a wide range of temperatures.
• Once the official jacket of the U.S. Forest Service.
• Antimicrobial and naturally insulating wool is ideal for outdoor adventures.
• Lifetime warranty.

The Filson Mackinaw Cruiser is one of the most famous and recognizable coats on the market. I’ve gone as far as calling it the best wool coat of all time. If you haven’t worn an unlined wool jacket before, this is the one that will make you finally “get” the hype around wool.

That it’s unlined means it brings wool’s full powers of insulation and breathability to bear: it insulated when it’s colder and breathes when it’s warmer, so it’s a fantastic piece to wear when the temperature will vary a lot — or when you just don’t really know how cold it will be.

The buffalo plaid appears everywhere, from classic films like “On the Waterfront” to survival games such as “The Long Dark,” and it was even the uniform of the US Forest Service for a while.

Downside, but not a deal breaker

Because it’s unlined, you will notice the 24-ounce wiry, scratchy wool. It is the kind that makes you think of frontiersmen and makes you wish it did have a lining, but the lack of lining means it breathes as well as it insulates, so there’s a much wider range of temperatures you can wear it in. So long as you wear long sleeves, it’s not too itchy.

But if that sounds like a dealbreaker, Filson’s Lined Jac Shirt is the same wool and same weight with a simpler design. (So it’s actually a little cheaper.)

What We Love:

• All the Powers of Wool: Tough, antimicrobial (you’ll likely never need to wash it) and above all breathable and able to be worn in a wide range of temperatures.
• Longevity: Lifetime warranty, even if you buy it used.
• Lots of pockets: Two on the chest, two at the cuff, handwarmers, and even a game pocket on the back where you can keep a beanie and gloves.

What to Consider:

• Comfort: The thick, scratchy wool isn’t for everyone.
• Style: It’s very casual.

Cheaper Alternatives

Heat Straps sells a similar jacket that’s cut a little shorter. The Lumber jacket is cheaper, but actually made with a heavier wool that’s also less scratchy; I can wear it with a t-shirt without issue. Stormy Kromer also sells a Mackinaw jacket, pictured right, made out of a 26-ounce 100% Virgin Wool.

Warmest Denim Jacket: Freenote RJ2

• Heavy 20-ounce Japanese selvedge denim.
• Lined with warm shearling.
• Bi-swing gussets provide mobility.

Transitioning from traditional to trendsetting, the Freenote RJ2 emerges as the pinnacle of winter denim jackets. We’re not entirely sure why, but it is next to impossible to find any other denim jackets on the market that are lined with shearling or even just regular wool; all those denim “sherpa” jackets are lined with polyester that just looks like wool.

So it wasn’t hard to make the warmest denim jacket but Freenote went as far as they could anyway, not only opting for ultra warm shearling over wool but also picking 20-ounce Japanese selvedge denim. This jacket is perfect for those who love a denim jacket but need something warmer.

Paired with heavy canvas pants (like Freenote’s!) or 21-ounce Iron Heart jeans, the RJ2 makes a formidable addition to any winter wardrobe. One thing’s for certain: you don’t need to worry about this jacket being warm enough!

What We Love:

• Stylish Warmth: Combines the classic appeal of denim jackets, including its ability to fade with wear, with the functional warmth of shearling lining.
• Rare: It’s incredibly uncommon to find a denim jacket made for cold winters.
• Good mobility: Includes design elements like bi-swing gussets and hidden elastic bands for ease of movement.

What to Consider:

• Very Warm: If it’s not cold enough, you’ll sweat as soon as you put it on.
• Price: As a niche, high-quality product, it commands a premium price.
• Sleeves aren’t lined with wool: But trust me, you won’t wish this jacket was warmer. Plus the sleeve lining is a half cotton half viscose blend; unusually “natural” for sleeve lining, which is usually where brands put synthetics.

Cheaper Alternative

It’s challenging to find any other denim jackets for cold weather. Nothing out there is as warm as this one, but for decent (if less effective) alternatives:

• Filson sells a denim Cruiser lined with a wool/poly/rayon blend.
• Iron Heart sells a denim Rider jacket lined with a cotton/wool blend.
• Or search for wool-lined denim jackets on eBay. For whatever reason, they used to be more common than they are now.

Best Peacoat: Buzz Rickson’s USN 1910s Peacoat

• 36-ounce Melton wool: warm, durable, and resistant to water and wind.
• Very versatile; great with a crewneck or a button down and tie.
• Replica of WW1 peacoat; will last another hundred years.

Next on the list is the peacoat, and we’re going with a replica of the version worn by the US Navy in World War 1.

Made by well regarded reproducer of historical garments, Japan’s Buzz Rickson’s, this is an authentic replica of early 20th-century naval peacoats, providing a great option for enthusiasts who appreciate historical accuracy — but it’s also just the warmest peacoat on the market.

Believe us, we’ve looked. The Filson Mackinaw was 24-ounce wool, this coat is 50 percent heavier at 36 ounces. It’s true that just about every clothing company has released their own version of the pea coat, but while we’re sure one exists, we haven’t found any alternatives that are thicker than the original.

So, it’ll last for a hundred years, it’s barely a hundred bucks more than the Mackinaw, it’s warm as all hell, but above all, it’s the smartest and most versatile jacket (or coat, whatever) on this list.

What We Love:

• Historical Accuracy: Buzz Rickson’s replica offers an authentic take on early 20th-century naval wear.
• Function: The 36-ounce Melton wool will keeps you warm in almost any conditions, plus that handsome collar protects your neck pretty well when popped.
• Versatility: The pea coat may be the most widely worn military garment. It’s just worn because it looks great and matches anything; we doubt most pea coat owners even know that it’s a naval piece.
• Not Itchy: This is melton wool, a super dense form that’s not only more water resistant, but less itchy than some of the coarser wool you’ll find on outerwear.

What to Consider:

• Weight: The heavy wool construction takes some getting used to.
• Fit: They’re quite trim, designed to emphasize (or appear to emphasize) broad shoulders and small waists. Heavier guys will want to size up, but even then the silhouette may not be quite right.

Cheaper Alternative

Schott NYC’s Peacoat is among the best known pea coats and it deserves the accolades it receives. Buzz Rickson’s is $685 — seriously, a great price for a versatile piece that will outlive you — while Schott’s American-made coat is just $390.

They managed this by dropping the wool density to 32oz and using an 80/20 wool/nylon blend. We’re not complaining when the price is this reasonable.

Warmest Jacket Ever: Canada Goose Expedition Parka

• Likely the warmest jacket you’ll ever find; it’s worn by Antarctic scientists.
• Packed with 625 fill power, responsibly sourced down.
• Modern and technical materials like a water-repellent polyester shell, nylon snow skirt, and velcro closures.

The Canada Goose Expedition Parka can handle even the most extreme weather conditions. It’s so effective that scientists at Antarctica’s McMurdo Station even use it to stay warm.

Filled with high-quality down, this parka is featured in pop culture (The Day After Tomorrow, of course) and rugged environments alike, earning its reputation as one of the warmest winter parkas on Earth.

We have a bias for natural materials here at Stridewise, and while the water-repellent shell is mostly polyester, there are all sorts of extra tech, like a nylon snow skirt and velcro closures.

The filling is where the wonderful natural insulator down comes to shine. Each ounce of Canada Goose’s 625 fill-down has approximately two million fluffy filaments that overlap to create insulating pockets of air that keep you warm.

Also, Ryan Reynolds donated several hundred to an Inuk community in the Canadian Arctic, where they were considered top notch for the incredibly harsh environment.

So, it meets our criteria of famous, cool, and warm. It does cost 1,700 bucks, and buddy, you probably don’t need something this warm. But if you do, now you know where to look.

What We Love:

• Extreme Insulation: Designed for the coldest environments on Earth, ensuring maximum warmth.
• Cultural Impact: Worn by scientists and celebrities alike, adding to its prestige.
• Functional: Packed with Arctic essentials like a down-filled hood, chin guard, snow skirts, six exterior pockets and three interior ones.

What to Consider:

• Overkill for Mild Winters: It’s likely too warm for less extreme climates.
• Investment Piece: Technical down jackets are expensive, it may be an unnecessary expense for a lot of people.

Cheaper Alternative

Multiple brands offer down parkas that are less expensive and still provide considerable warmth from cozy down. I recommend the Polar Expedition from Fjallraven or the Moose Knuckle Original Stirling Parka, with real fur. For a significantly cheaper alternative there’s always the classic North Face Down Parka.

Wrapping Up

These aren’t your one-season-and-done winter jackets. These cultural icons will never go out of style or leave you freezing.

With any of these choices, you are turning the cheek to fast fashion, standing firm on tradition, and demonstrating the incredible warmth of natural materials like shearling and down.

Overall, these highly functional, relatively minimalist takes on outerwear are at home anywhere from ice fishing with your cousin, who always has something to say about what you are wearing, to taking your date to a holiday market in the city. So, even if your closet is limited by size, we are confident these coats are worth buying, keeping, and strutting in for seasons to come.