There’s never been a better time to be a pants-wearing human being. From a sheer selection standpoint, the current era is without rival. Whatever you’re pulling on, a cornucopia of fits and finishes awaits you. Options truly abound.
But abundance is a double-edged sword. The other day, I was talking to the head of men’s fashion at a major American department store, and he let me in on a secret: Men aren’t buying pants. They buy knits and jackets and sneakers—but nothing for their legs. The reason, I suppose, is that the volume of choices can leave some folks feeling confused. Paralyzed, even. Call it the tyranny of choice. You’d have to be some kind of borderline-obsessive pants enthusiast to come close to exploring all the stuff on the market.
Luckily for you, the Esquire office is full of borderline-obsessive pants enthusiasts. We’ve tried the skinny, the slim, the slim-straight, the straight, the baggy, and the ultra-baggy versions. We’ve played around with preferred rises. We’ve worn pleats—hell yeah, we have!—and flat fronts. Cropped cuts and ones that pool just so at the ankle. Wide legs and boot cuts. We’ve fixated, futzed, and failed to hit the mark a few times along the way. And we’ve done all that so you don’t have to.
If you’re in the market for a new pair of pants, this is where to start. We are going to lay out four essential styles—jeans, chinos, trousers, and suit pants—and steer you in the right direction. We’ll cover fabrics, washes, prints, and patterns. But most importantly, we’re going to talk about fit. And rather than leave everything open for interpretation, we’re going to put some guidelines in place so you can land somewhere near the happy medium—the sweet spot—of how any given pair of pants should look and feel these days. (You can veer outside of them, of course, but remember that understanding the so-called “rules” is the best foundation for breaking them successfully.)
Let’s get into it.
Jeans
A higher rise and straight leg will never go out of style.
Denim is the cornerstone of most wardrobes. It’s tough, it’s cool. Goes with pretty much everything. Which is why it’s a little frustrating that right now, it’s arguably the most confusing part of the market on the fit front. There’s no longer one style that reigns supreme. In fact, pretty much any cut your imagination can conjure is currently sold at a huge swath of stores across the entire spectrum of price points.
If you’re unsure what works for you, jeans-wise, it’s best to aim for the middle. A straight-leg cut with a medium to medium-high rise will work for pretty much any body type, and it has proven itself the most enduring of denim styles over nearly a century. Start with the Levi’s 501 as inspiration and expand your search from there. Wrangler’s Cowboy Cut leans a little more Western, but if you opt for the “original” instead of the “slim” version, you won’t look like you just stepped out of a honkytonk. Lee’s Rider jeans are narrower, but don’t get too skinny. There are also options from American lifestyle brands like Ralph Lauren, Todd Snyder, and Buck Mason as well as versions from denim specialists like 3Sixteen and OrSlow. A.P.C., Nudie, and Uniqlo were gateway drugs for a lot of committed denimheads for a good reason, and first-wave denim boom brands like Rag & Bone and Citizens of Humanity (check out the collab with Billy Reid) are still turning out very strong work.
Pairing with horsebit loafers is emphatically recommended.
Honestly, though, it’s less about maker and more about going for something that feels timeless. If you want to get narrower or wider with the fit, go for it, but know that when you start hitting the extremes—skinny on one side, ultra-baggy on the other—your risk of looking dated (or like you don’t know how to dress your age) increases exponentially. Take your pick of colors but remember that white is underrated and indigo will never do you wrong. Washes are best kept realistic, and holes and distressing minimal. Remember those shredded, calf-strangling biker jeans from years ago? Yeah, we don’t want to, either.
Levi’s 501 Original Fit Jeans
Wrangler Cowboy Cut Original Fit Jeans
Todd Snyder Vintage Straight Selvedge Carpenter Jeans
Nudie Jeans Steady Eddie II Indigo Nights
Chinos
A slimmer cut looks great, but make sure it doesn’t get too slim.
For a long time, we suffered under the mass delusion that the best way to modernize the chino was to shrink its proportions. When the legs started getting less billowy and the pleats started disappearing, it felt fresh. Youthful. Then chinos started getting skinny. Their popularity took off and early adopters watched them filter into the mass market. It didn’t take long before slim, stretchy chinos became the de facto business casual uniform for young professionals and middle-aged politicians alike. Which, naturally, made them feel a lot less fresh and youthful and a lot more like the anti-style signifier their baggy brethren were a decade or so prior. Call it the Great Chino Inversion.
Nowadays, then, the best move is not toward slimmer styles. All those “commuter pants” and super-stretchy riffs on chinos may be comfortable—they’re basically leggings, after all—but they pale in comparison to the genuinely fucking cool vibe you can get from a pair of chinos that take their cues from mid-century versions. We’re talking about heavier fabrics, wider legs, higher rises, and a feel that’s inspired by their utilitarian, military roots. That doesn’t mean you can’t get something that’s polished and office friendly. It just means that it shouldn’t look the least bit tech-y, and the contours of your calves should not be visible. Crisp cotton will look far better, especially over time.
Classic khaki is always a good idea, but if you want to mix it up, washed-down black is a fantastic casual option.
And speaking of time, when you’re off the clock, you can go for something a little looser—maybe even with a little wear and tear. (Once your work chinos are looking particularly well-loved, just turn them into casual chinos!) Wherever you want to wear your chinos, shopping for them isn’t thatdifferent from shopping for jeans these days. Todd Synder, Ralph Lauren, and Buck Mason do a great job with them, as do Alex Mill, Billy Reid, and—no surprise here—the team at Dockers, though you should avoid non-iron options. If you want to get a little preppier, J.Press and Brooks Brothers are always there for you. If you prefer your prep with a little skate influence, there’s Noah. And we can’t talk chinos right now without talking about J.Crew. Brendon Babenzien (also the creative director of Noah) is the men’s creative director, and he’s leading a new era of menswear that includes the smash-hit giant-fit chino, which is actually not all that giant but loose and cool and well worthy of your consideration.
As for colors, you can’t go wrong with classic khaki. (We like it a little darker, closer to sand or caramel than bone white.) Olive is great. So is navy, especially if you want something that works nicely with a textured sweater and a white oxford shirt. On the embellishment front, pleats are absolutely acceptable. Critter embroidery—think tiny lobsters or horses or what have you—is largely to be avoided, unless you’re a preppy pro.
Polo Ralph Lauren Salinger Straight Fit Chino Pants
Buck Mason Paperback Twill Full Saddle Chinos
Brooks Brothers Advantage Chino Pants
Alex Mill Standard Pleated Pants in Chino
Trousers
As seen here, trousers don’t have to look like something you’d wear to the office.
There are a lot of places you can go with trousers right now, but as with jeans and chinos, the biggest piece of advice we can offer is to avoid something too skinny. You know those guys in trousers with a pattern that distorts as it makes their way down their legs? It’s all skewed lines and geometric confusion here, pulling seams and scrunching pockets there? It’s because their trousers are entirely too tight. The skinny-fit-everything mania that’s still causing problems throughout the style world might be even worse for your overall appearance in tailored clothing than casualwear. Lighter fabrics and more use of prints and patterns mean that every place your pants are pulling and bunching is all the more evident to the naked eye. Luckily, there are two easy ways to fix it, both of which we heartily endorse.
The first is, of course, to ensure your trousers fit. A lot of people wind up sizing down in search of a slim leg, which throws everything else—most notably the waist, seat, and crotch—all out of whack. The pockets scrunching up and forming little Dumbo ears at your hips? It means your trousers are too tight. So start with the right size and then search for the right cut. We can’t stop you from going slim or low-rise here, but we can point out that the line created by a fuller leg and a higher rise creates a more flattering shape for pretty much everyone, elongating and slimming your silhouette instead of making you look stumpy. Part of that equation is finding the right length. While cropped has been the move for a while and experimental types sometimes opt for extensive inseams, you can’t go wrong now and in the near future with a light-to-full break, where the front of the pant actually meets the top of your shoe, whether just skimming it or sitting heavily enough to produce a full (single!) fold.
If you’re going with a looser leg, feel free to wear them a little longer.
After that, you can opt for a fabric that’s got enough heft to give your trousers the proper drape (and a little more durability). Ultralight, technical fabrics or thin wools may sound fancy, but in practice they don’t tend to wear well. They’ll crease. They’ll pucker. They just won’t look as good as something with the necessary degree of oomph. Prints and patterns work, as do solids, but the guiding principle here is that a mid-gray is going to be one of your best bets to work with tailored clothing, while darker colors (say navy or black) tend to work better with casual or—dare we say it?—fashion forward looks. Wild colors and loud prints shouldn’t even enter the beginner-level discussion.
While we love natural fibers, if you’re looking for something inexpensive to start your trouser journey, Uniqlo makes a particularly affordable wide-leg pair with a hidden stretchy waist out of a polyester/rayon blend that does a commendable job of mimicking the look and feel of wool. Cos does a great job with more accessible trousers, too, though the selection of styles changes more rapidly than it does at Uniqlo, so if you’re in the market and you like what you’re seeing, hesitation is not your friend. In a similar bracket, price-wise, but far more traditional is the offering at Spier & Mackay. Stepping up from there, you’ve got all the lifestyle brands we’ve mentioned before to explore, plus cool-guy players like Our Legacy, Officine Générale, Lemaire, Stòffa, Studio Nicholson, Loewe, and more. Brunello Cucinelli makes a mean pair, of course, as does Canali. And then there are the legacy luxury fashion houses like Louis Vuitton, Gucci, Burberry, Dior, Hermès, Armani, Loro Piana, Versace…the list could go on and on.
A cuff adds some visual interest as well as weight to ensure your trousers hang properly.
Suffice it to say: A lot of folks are making very good trousers right now, from the impulse-buyable all the way up to the investment level. Make sure you have enough room to move comfortably and keep the rise high enough that you’re nowhere near plumber-butt territory, and you’re pretty much golden.
Uniqlo Pleated Wide Pants
Cos Turn-Up Wool Blend Pants
Brunello Cucinelli Tapered Pleated Virgin Wool Trousers
Suit Pants
Whether loose or slim, it’s all about striking a proportional balance with the suit jacket.
Really, suit pants are just trousers that are made of matched fabric alongside a suit jacket. So most of the stuff we just described above holds true for them. That said, the biggest thing to consider here is how the trousers interact with the look of the suit. If you’re quite slim and opting for a slimmer cut on the jacket, you don’t necessarily want wider-leg pants. It’s all about balance.
A wider leg will prevent you from looking like a box perched on a couple of toothpicks.
For most people—we’re talking the vast majority, here—it’s still advisable to shoot for something with more classic proportions: a jacket that drapes but doesn’t pull, and trousers cut straight enough to continue the elegant lines of said jacket all the way down to your feet. You know those guys in bigger jackets with tight pants? You know how they look like a box sitting on top of a couple of toothpicks? That’s exactly the sort of shape you want to avoid.
As for where to get these trousers? Check the trousers list above first, then supplement your list—and your tailoring knowledge—with our story on the three suits every man should own. Happy hunting.
Boglioli Straight-Leg Cotton-Blend Suit Trousers
Suitsupply Wide Leg Straight Pants
Abercrombie & Fitch A&F Collins Tailored Suit Pants
