Where should we even start? No doubt the most popular pant design in the world, the 5-pocket jean is beyond a wardrobe essential—it is a fundamental necessity. Referring to the iconic silhouette—two rear pocks, two side pockets with a small hidden “coin” pocket hidden within the right hand side—the 5-pocket jean is the cornerstone of modern menswear. While the pants’ origin is far too long to adequately summarize here, what is actually crucial is owning a pair. Whether vintage, designer or simply a solid pair of Levi’s 501s, if you don’t own a pair of classic 5-pocket jeans, your wardrobe is incomplete.

Fit
How 5-pocket jeans are supposed to fit is a tough question, especially considering the sheer variety of styles and shapes. While we currently gravitate towards straight leg denim, each body is different. Our tip is to start off with a pair of straight or slim-straight denim and experiment from there. Conversely, our denim fit guide breaks down each and every fit so you can find exactly what you’re looking for.

Recommended Brands
$: Levi’s, Wrangler
$$: Acne, A.P.C.
$$$: RRL, Dior

For additional recommendations, check out our favorite jeans here

While work pants have been trending in general as of late, the carpenter pant stands above the rest. Whether in denim or the ever-sturdy duck canvas, the workwear standard is prized for its blue-collar origins and utilitarian qualities. Boasting an impressive number of pockets intended for various purposes—from holding pliers to a hook to hang a hammer–the pant crossed over from mechanics to the fashion realm precisely due to its incredible practicality. While the Dickies Double Knee pant is an unimpeachable classic, high-fashion iterations from the likes of Junya Watanabe and Helmut Lang are proving that carpenter belong in more than just your car-obsessed uncles garage, but your closet as well.

Fit
While some fashion forward takes on the carpenter pant come in comical proportions, are advice is to stick to the classic straight fit. This is a garment intended to be worn while working in a shop, so anything restricting—or conversely, baggy and likely to get caught—is a no go. Carpenter pants should be fitted at the waist, wide at the thigh and straight through the rest of the leg. Whether you’re working on your car or just going for a coffee run, a greater pair of carpenter pants will do just fine.

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

Of the countless ways military style has influenced civilian wardrobes, the cargo pant is arguably the most prevalent. Between the BDU cargo and the fatigue pant, since the introduction of the G.I. Bill, military issue cargos have been a central part of the male wardrobe. While military surplus options are great, nearly any menswear brand worth it’s salt has embraced the cargo and the relaxed fit—not to mention the sheer number of pockets—are a stellar edition to any wardrobe. From skaters to runway diehards, nearly everyone is wearing cargos (and you should too).

Fit
A great pair of cargos should fit as the army intended—baggy. That said, for those with a shorter stature or leaner frame, a slimmer silhouette may work just as well. The most important aspect of any great cargos is material (preferably ripstop, but nylon will suffice) and length, which should be a traditional break, meaning the hem should hit right above the sole of your shoe.

Recommended Brands
$: Rothco
$$: Engineered Garments
$$$: WTAPS, Julius

Though the “transitional” wardrobe concept–clothes ideal for the office and drinks afterwards—is a tad dated, its critical component is not. The chino is, at it essence, a pant for all occasions. As easily dressed up as it is down, you will find yourself pulling it out of your closet time and again for any number of reasons, from a day at the office to an easy pant for vacation. While straight leg khaki iterations may feel staid, more modern pleated, slightly cropped iterations in a wider variety of colors have given the pant new life.

Fit
While classic chinos such as Dickies 874 work pants fit straight or relaxed, other takes on the closet staple vary greatly. Considering how versatile the pant is, there’s no wrong option here and a slim pair is just as suitable as Japanese ultra-wide version depending on your personal style. If you’re not sure which direction to go, stick with the classic and try a good old Dickies 874—they’re a classic for a reason.

Recommended Brands
$: Dickies, Carhartt
$$: Carhartt WIP, Ami
$$$: Junya Watanabe, Undercover

Considering the countless variations on the silhouette, trousers arguably warrant an entire article on their own. Between suit pants, wide low-rise avant-garde iterations and slim modern designer cuts the category is exploding with options. In general, a trouser is any wool or cotton pant featuring a flat front and designed with at least an air of formality. Recently trousers have become a streetwear favorite, with brands from Stussy to Supreme regularly including them in seasonal collections. Plaid is currently on the rise, but for those looking for something more versatile, a wool blend will work all year long.

Fit
Following current trends, wide and baggy trousers are currently extremely prevalent, both on the street and runway of Grailed favorites including Maison Margiela and [Jil Sander](https://www.grailed.com/designers/jil-sander]. While we recommend a pair of wide trousers—fitted at the waist and hem but huge everywhere else—we realize the silhouette is not for everyone. For those looking for more reserved option, a slim straight cut with a taper below the thigh is timeless.

Recommended Brands
$: Stussy, Supreme
$$: Lemaire, Our Legacy
$$$: Maison Margiela, Yohji Yamamoto

Essentially trousers with an elasticated waist, the “easy” pant went from grandpa’s favorite to one of the most prevalent bottoms in fashion. With the rise of normcore and dad style, the lightweight silhouette began picking up steam over the past two years and is now a bonafide wardrobe staple. Packable, durable and surprisingly formal, the pant is no longer just for geriatric activities but perfectly suited for damn near everything.

Fit
As the name implies, the easy pant should fit... well, easy. Consider sizing slightly down—the waist is elastic—but for those who feel that wide leg trousers are too aggressive, this is your opportunity to inch out of your comfort zone. Brands that toe the line between athletic wear such as Snow Peak and White Mountaineering specialize in the cut, a wide and heavily tapered leg with a snug waist, simultaneously fitted and baggy.

Recommended Brands
$: Club Monaco
$$: Ami
$$$: Lemaire, Martine Rose

While the tracksuit trend may have peaked over a year ago, the style—while perhaps slightly overdone–is still just as relevant today. Once relegated to soccer chads and dad’s attempting to relive the glory days, the track pant entered the fashion consciousness with the proliferation of English hooligan and roadman style over the past five years. Brands such as Kappa and Puma both underwent a massive resurgence, and suddenly the football staple began appearing on Margiela runways. While the slim and sporty cut is best left on the field, modern straight leg interpretations are exceedingly comfortable and are a perfect alternative to trousers or easy pants. If you need a new pair of pants to pair with sneakers, the grosgrain stripe on most track pants compliments kicks perfectly.

Fit
As noted above, the traditionally skinny warm-ups aren’t doing any of you any favors. Instead, consider a slim or straight leg cut in a more luxurious material rather than an entry-level cupro or modal. For those willing to push boundaries, a straight leg fit track pant paired with boots is a wild combination that surprisingly stuns.

Recommended Brands
$: Kappa
$$: Needles, Yeezy
$$$: Maison Margiela, Grace Wales Bonner

It’s no secret that sweatpants have transformed from a lazy Sunday favorite to a core part of the male wardrobe. More than simply a consequence of our increasingly casual dress code, quality sweatpants are inarguably the most comfy bottoms in any man’s closet. While brands like Reigning Champ helped elevate the casual sweatpant via premium cotton and higher-end fabrication, the garments transformation is largely due to street style stars like Kanye West to Jerry Lorenzo who not only regularly wear the garment, but made them a permanent fixture in their respective seasonal collections. Today, sweats range from $15 Champion basics all the way to four-figure versions by the likes of Chanel and Dior

Fit
Modern sweats tend to skew towards slim, however we recommend going an alternative route and buying a more straight cut or baggy pair. Considering with sweats comfort is key, don't be afraid to go a size up. In this case bigger is better.

Recommended Brands
$: Reigning Champ, Champion
$$: Yeezy
$$$: Haider Ackermann, Fear of God