If you don’t own a denim jacket already, stop reading now and purchase. They’re that good. Whether it’s a beat-up hand-me-down Levi’s Type-E you found in dad’s closet or a high-fashion Tom Ford iteration, the denim jacket is a critical component in any man’s wardrobe. They’re perfect for fall, work with pretty much any pant that’s not the exact same wash and during winter can be worn under a coat akin to a heavyweight Western shirt. Alternatively referred to as a Trucker jacket due to its traditional Americana heritage, the denim or jean jacket is a workhouse that will last for years.

Fit

A denim jacket (when new) should be tight in the shoulder and arm, as over time the denim will break and mold to the wearers body. Generally cropped, most denim jackets hit your true waist slightly above the hip, and will hug back before gently giving and squaring off towards the hem.

Recommend Brands
$: Levi’s
$$: Acne, RRL
$$$: visvim

Although last year’s fleece trend hit a fever pitch, the jacket’s popularity will no doubt continue through this fall well into winter. Popularized by outdoor brands such as Patagonia and The North Face, the fleece is one of the most versatile jackets in the menswear arsenal. Available in a slew of fabrications, the surprisingly technical “pile” fabric is famous for its breathability and warmth, as suited for a breezy 50 degree fall evening as a chilling sub-zero mid winter freeze. For those seeking a comfortable, practical and stylish jacket, the fleece is it.

Fit

A good Fleece should be roomy, slightly oversized for additional warmth but never overtly large—unless you are buying a fashion-forward Martine Rose iteration and that’s the desired aesthetic. The shoulders will be relatively fitted however sleeves will have room to spare to make room for sweatshirt or hoodie. Don’t worry about going a bit large, as most have cuffed sleeves regardless.

Recommended Brands
$: Patagonia
$$: Supreme, Palace
$$$: Alyx

More than your high school letterman jacket, a varsity is as classic an example of American style as any. Most often sporting a felt body with leather sleeves, the jacket reeks of nostalgia while still offering next level comfort, warmth and looks undeniably cool to boot. Originally designed to keep athletes warm between plays, the jacket is ideal for the cold winter months. Today a streetwear staple, the item is constantly gracing the backs of skaters and downtown impresarios, but due to the genre’s surging popularity and high-fashion crossover, the runway letterman is more common than ever.

Fit

As opposed to your high school hand-me-down, the modern varsity is far less raggedy. Either in felt or leather, the sleeves should be bulky and fit relatively straight, while the shoulders will be fitted and body somewhat wide. A great varsity will hit somewhere below the waist a bit more substantial of a jacket suited for the end of fall or even winter.

Recommended Brands
$: Golden Bear, Nike
$$: Supreme
$$$: Louis Vuitton

It may seem obvious, but most be noted nonetheless—you need a raincoat. No matter where you live, it’s bound to rain and even the most luxurious of umbrellas eventually will not cut it (not to mention, it’s impossible to look cool with an umbrella). Instead, consider a taped-seam, waterproof alternative. Either cropped at the waist or 3/4 length—somewhere between mid-thigh and back of the knee—a true rain coat provides the sort of protection that only technical innovative fabrics can. If you’re really looking to splurge, search for higher end renditions featuring Gore-Tex.

Fit

Whether short or full length, raincoats should fit loose, as the further from your body the water the better. Remember, no matter how good a raincoat is, eventually water will seep through, so anything tight to the body will inevitably bleed through to the layers underneath. As for basic principles, as long as the shoulders sit snug and the hood is large enough to cover your head, you should be good to go.

Recommended Brands

$: Rains
$$: Stutterheim, Acne
$$$: Acronym, Veilance

An eternal symbol of cool, few items are as unabashedly bad ass as a great leather. Since Marlon Brando donned a Schott Perfecto in The Wild One, the leather jacket has been a symbol of unbridled machismo. Yet, despite the jackets overtly masculune connotations, numerous styles and an inherent warmth have transformed the leather jacket into an undeniable essential—literally any men’s wardrobe guide says as much. While the “perfecto”—otherwise known as a Rider jacket or moto—is the first and most prevalent, other styles, including the cafe “racer” jacket or flight jacket with shearling collar, may be more suitable for those looking for a less aggressive look. Any of the three is well-suited for fall and over a sweater or under a heavier piece of outerwear is a shield naturally designed to withstand winter, literally.

Fit

Motorcycle Jackets should be tight—and we mean it. For those buying vintage it’s a different matter altogether, but anything somewhat new (even if used) will have a significant amount of stiffness, which will inevitably break and fade over time. The usual guide is if you can just barley close the zipper, with due diligence and adequate wear, the jacket will be perfect.

Recommended Brands

$: Schott, Falcon Garments
$$: Acne
$$$: Undercover, Rick Owens

From dad’s old Alpha Industries to actual vintage B-1 flight jackets, the bomber is the textbook example of how military garments invaded civilian style in the aftermath of World War II. Today, the jacket is a streetwear staple and while its air force connotations are lost on many, its latent technology is not. Originally designed to be worn by fighter pilots at high altitude, these jackets are engineered to keep you warm—plus look great on top of your favorite hoodie. If you’re interested in a jacket that will last from fall through spring and onwards, buy a classic bomber. There's a reason eternally stylish men from Shia Labeouf to Kanye West rarely leave the house without one.

Fit

A true “bomber” jacket should be short and wide, sitting at your waist and snug to your shoulders. While modern or high fashion iterations may run a tad slim, considering opting for something with more spacious sleeves to allow for layering. Though these jackets are designed to sit wide, try and avoid anything with too much body, or you will look like you’re swimming in your own clothes.

Recommended Brands
$: Alpha Industries, Supreme
$$: Acne, Our Legacy
$$$: Maison Margiela, Rick Owens

From your little league coach to Otter’s baby blue Members Only jacket in Animal House, the coach’s jacket is an American icon. Alternatively referred to as a blouson, the lightweight jacket—most often in nylon but regularly available in other materials including wool and leather—has been a canvas for menswear designers for decades. Slim, lean and with few embellishments, it’s the perfect early fall or spring workhorse, regularly made from sturdy ripstop and able to take a battering. If you find yourself in a climate where it gets cool, but never too cold, a coach’s jacket is the perfect solution.

Fit

Coach’s jackets should fit relaxed, never too slim or oversized. Designed for a streamlined look, any jacket that sits too wide on the shoulders or to snug on the back will not only be uncomfortable, but look awkward as well. For best results, stay true to size and pair with a minimal wardrobe.

Recommended Brands
$: Member’s Only, Stüssy
$$: Palace, CDG Comme Garçons](https://www.grailed.com/designers/comme-des-garcons)
$$$: Needles, Stone Island

At the center of workwear stands the, well, work jacket. Composed of sturdy duck canvas with reinforced elbows and two hidden pocks at the waist, the pride of every mechanic and contractor's uniform has worked its way into guy's closets everywhere. Though intended for doing actual manual labor, the jacket's simple construction and utilitarian nature helped it transform into a fashion favorite, particularly as of late. Additionally, a fully lined interior means that when fully zipped the work jacket functions just as well in fall as in the dead of winter.

Fit
Work jackets should be slightly cropped, relatively straight and sit tight at the shoulder while framing the back. More fashion forward iterations will fit slimmer through the torso, but in general as the fabric "breaks" the jacket will expand, so consider sizing down until the jacket perfectly molds to your body.

Recommended Brands
$: Dickies, Carhartt
$$: Carhartt WIP
$$$: Junya Watanabe, Helmut Lang

Of the countless ways military has influenced the male wardrobe, one of the most enduring is the M-65 jacket. What was once standard issue for U.S. troops is now a perennial style staple. In the best shade of olive, the jacket has donned the backs of beatniks, hippies, punks and skaters, subverting it's intended purpose numerous times over. Today, it's simply a great layering piece that adds a bit of edge to your wardrobe without going over the top.

Fit
M-65 jackets should be fitted at the shoulders however sit loose in the waist. Designed to be worn over a military uniform, the jacket will be wide in the arms, perfect to wear over a hoodie in the early fall.

Recommended Brands
$: Rothco, J. Crew
$$: Needles
$$$: visvim, WTAPS

When it's cold—and we mean really cold—you need a down coat. Whether synthetic or goose, down is truly the only fill that can withstand sub-zero temperatures, and few jackets utilize it better than the puffer. While Seinfeld meme's may be top of mind, the modern puffer is anything but Costanza's massive parka—though Gore-Tex may be involved. A pervasive trend throughout the '90s and a strong association with the New York hip-hop scene helped the puffer enter the streetwear canon and through brands like The North Face and Canada Goose the jacket went mainstream. Though some are better than others, if you stick to a clean silhouette, you won't be sorry.

Fit

While puffers are traditionally oversized, in this case we encourage the opposite. Size down to the point where the jacket hugs you similar to a fitted bomber—you'll avoid the Costanza associations while still keeping just as warm.

Recommended Brands
$: The North Face
$$: Supreme, Palace
$$$: Moncler, Alyx

Tracing its roots back to the 18th century Netherlands, the peacoat transformed from standard issue naval uniform to menswear go-to in much the same way other military garments did. After generations of vets began wearing the heavy coat off-duty, the style picked up and eventually was adopted by beatniks before picking up steam with the menswear set as an enduring symbol of Americana—Dutch lineage notwithstanding. While the cropped coat is not for everyone, for those of you who feel that a full length trench is simply unnecessary, the mid-calf cut Pea Coat is your best option. Made of a thick-gauge wool ideal for harsh open-ocean climates, a great peacoat will literally survive a perfect storm.

Fit

Originally designed for active seaman, Peacoats sit wide on the body with fitted shoulders and wide arms allowing for heavy lifting. While traditional replicas by Schott or Spiewalk will fit much the same, more modern luxury iterations made from cashmere or lambswool will be decidedly more fitted.

Recommended Brands
$: Schott
$$: Comme des Garcons Homme, Helmut Lang
$$$: Brunello Cucinelli, Maison Margiela

An outdoor staple, the hunting jacket has been an icon of rugged style for decades, the most famous of which is the Barbour jacket. Dating back to 1894, the Barbour jacket originated in Simonside, South Shields in northeast England. Utilizing a water resistant waxed cotton exterior, the jacket brilliantly repels rain and perfectly blends into the forest, ideal for hunting quail and big game. Despite it's sportsman origins, the jacket became closely associated with WASP culture and Ivy style, and over the course of a century wound up in nearly every man's closet throughout the northeast United States. With the resurgence of prep, the jacket has once again entered the mainstream, a timeless symbol of Americana. More than simply a raincoat, a waxed cotton jacket is a symbol of the outdoors.

Fit

A classic Barbour jacket was oversized, worn over a hunting vest and various other layers. To that end, while modern day versions are cut substantially slimmer in the sleeves and body, do yourself a favor and buy this jacket a size up. As long as the shoulders fit, for this particular silhouette, the bigger the better (within reason).

Recommended Brands
$: Polo
$$: Barbour
$$$: Belstaff

Most often associated with fighter pilots, the shearling jacket is in fact the oldest garments on this list, considering humans have worn animal hides for generations. Technically speaking, a shearling is a lamb or sheep hide with the wool still attached and formed into a coat. Rather than stretching and tanning the hide to create traditional leather, the jacket is left essentially raw for a rugged effect. While there are numerous styles and fits, they all have one thing in common–they're incredibly warm. For those who aren't interested in a full length coat, a cropped shearling bomber is the way to go. Though they may look menacing, they are surprisingly easy to pull off.

Fit

Of the countless shearling iterations, the B-3 bomber is by far the most popular. Originally worn by Royal Air Force pilots, the jacket was painfully reproduced by Schott in near identical proportions. The fit, as was intended, is cropped and snug. You would be wise to stick to those proportions. Consider sizing down when buying an unworn jacket, as the leather starts stiff and breaks with age.

Recommended Brands
$: Schott
$$: Acne
$$$: Saint Laurent, Maison Margiela

If a modern rain jacket (see above) is too technical for you, a trench coat is the clear choice. Though named after the trench wars in World War I—where many soldiers wore the jacket while fighting in the trenches—the jacket was in fact created more than thirty years prior, when Burberry founder Thomas Burberry supposedly invented water-resistant gabardine twill. Fusing the then revolutionary fabric with a traditional officer coat, the trench coat was a revelation, military de rigueur for generations. Eventually, like many military garments the jacket found its way into the mens wardrobe, not only due to utilitarian practicality but aesthetic appeal as well. In the 100 years since, the jacket has wound up on more "men's essential" list that you could possibly count, considered by many the cornerstone of a man's wardrobe. While those opinions are slightly dated, the jacket itself it still a menswear hallmark.

Fit

The original trench coats were designed for soldiers and as such are inherently practical, cut fitted throughout with a slight flare at the bottom hem for added mobility and many modern interpretations fit in much the same way. For those with a more classic sense of style, that's your best bet. Still, more avant-garde iterations can be tempting, whether they are on the verge of skinny (Saint Laurent) or downright gargantuan (Maison Margiela). Regardless, make sure the shoulder and the waist fit accordingly, and the built-in belt never hurts.

Recommended Brands
$: Burberry
$$: Junya Watanabe, Supreme
$$$: Maison Margiela, Saint Laurent

The overcoat is an all encompassing category, ranging from the almost too slim topcoat to the slightly outdated car coat. Predominantly made from wool or wool blends, most overcoats contain slight canvassing and structure in the shoulders—through increasingly brands such as Marni are doing away with structure entirely. Usually at least somewhat formal, the category can feel overwhelming, except for one outlier: the camel coat. Sitting leagues above the rest, the double-breasted camel coat is at the pinnacle of outerwear, an easy throw-on that the works with seemingly everything in the wardrobe. Whether it's the infamous Polo camel coat that started it all of a lush mohair blend from Louis Vuitton, if you need a coat for every occasion from job interview to wedding reception and everything in between, this is it.

Fit

The beauty of a double breasted coat is that by its nature its structured to accent your best features. Stiff shoulders add width to your frame while the wide body is masked by the overlapping dual buttons. Essentially, as long as the shoulders fit and you can comfortable close the jacket, it will fit just fine.

Recommended Brands
$: Polo
$$: Ami
$$$: Louis Vuitton, Rick Owens