Somehow, tailoring is both simple and complicated. You can spend thousands and look terrible, and you can spend far less and look like a million bucks. It’s all down to the little details. The care you take over the fit on the shoulder, the way you wear your trousers, and the shoes you choose to finish it all off.
There are countless tips for getting it right—and you can find them all on Esquire—but sometimes it’s easier to talk about what not to do, which is why I’ve pulled together this list of tailoring peccadillos. All the little mistakes and bad habits that turn good tailoring, which is truly a man’s best friend, into bad clothing. After all, we learn more from our failures than we do our triumphs.
How Your Jacket Should—and Shouldn’t—Fit
The most common tailoring mistake I see is a too-short jacket. Over the past decade or so, the hems of store-bought tailored jackets have been creeping upward, and where once they easily covered one’s backside, they now often don’t, which is a great shame as it kind of defeats the object of the garment altogether. A great jacket will elongate and slim you with a swooping shape, and the shorter and boxier the jacket, the less likely that is to happen. A good rule when trying something on is to make sure the hem runs as low as the centre of your palm (with your arm at your side), but if you’re not sure, just look in the mirror. The jacket should cover most, but not all, of your ass.
Way too short on the jacket, Matt.
There are exceptions. The house style at brands such as Ralph Lauren and Thom Browne is purposefully short (in fact Browne’s is downright skimpy). And modern, more casual, workwear-skewed ‘suits’—like those at Uniqlo or Arket—tend to be cut shorter and boxier than classic tailoring. But they look better with a T-shirt and sneakers than they do a shirt and tie.
A workwear-leaning jacket from Buck Mason.
Overall, it’s better a jacket be slightly too big than too small, because you can always take away, but you can’t add. You’ll know if a jacket is too small if there’s a crease running horizontally at the top of your back—which means it is pulling too tight between the shoulders—or if there is a gap between shirt collar and jacket lapel at the back of your neck.
A correctly fitting jacket should button easily without pulling or creasing, and without the lapels bowing outward from the body. Sleeves, which are a subtle signifier of a correctly (or incorrectly) fitting suit, should be smooth and uncreased, and finish just above your wrist bone, allowing for a glimpse of shirt cuff.
The perfect fit.
Broadly speaking, a jacket can be structured or unstructured, referring to the type of padding, architecture, and finish at the top of the chest, arms, and shoulders. I have quite broad, square shoulders so prefer the comfort and ease of movement of unstructured (and if possible, unlined) tailoring, but you do lose some smoothness in the fabric, so it tends to be more casual. If you want that classic, Barack Obama, presidential finish, go for something more structured.
Muscly dudes—and there are more than ever—tend to assume that tight tailoring will accentuate their muscles, but you just look like a beefy guy in a bad suit. A great suit is flattering in its evenness and consistency, so if you’re super jacked, maybe just opt for a knit polo and dress trousers. It works for Dwayne Johnson.
Can Conor McGregor even move his arms in this suit?
Other little things to look out for include the crossed basting stitches on the cuffs and vents of a jacket when you buy it. They are just to hold the shape of the jacket in transit, in store etc., so snip them out as soon as you can.
Look out for skinny lapels, which were cool for indie-band frontmen 15 years ago, but now just look trash. Super wide lapels are kind of ridiculous, too, but generally, a wider lapel (be it notch, shawl, or peak) pertains to higher (or at least more considered) quality. And never fasten all the buttons on the front of a jacket. It’s a weird quirk of menswear, but always leave the bottom button of a jacket undone (unless it has just one button).
How Your Trousers Should—And Shouldn’t—Fit
The worst mistake you can make with suit trousers is for them to be cut too low at the waist. They are not jeans, they are not joggers; they should sit at your natural waist, which runs above your hip bones.
The Tate brothers prefer a low-rise trouser. You should not.
Length comes next, and too-long trousers are probably worse than too-short trousers, but only just. Anything that puddles over a shoe is schlumpy and makes you look shorter. But anything too cropped shortens you, too—a mistake I have often made. I like my suit trousers to just touch the shoe, but anything shorter looks dopey, like a toddler at a wedding.
Cary Grant just plain nailed it in To Catch a Thief.
Suit trousers can be slim (my preference) but you still need room in the thighs, calves, and seat. Pleated trousers can help with that, but the aim is not to “fill” the pleats, so to speak—they should still be flat and folded when you’re wearing them.
A subtle taper in the leg is fine, but nothing too narrow at the bottom, and nothing that feels tight around your ankle. If your pockets are bowing outward—an extremely common tailoring mistake—your trousers are too small around the seat. And speaking of trousers pockets, just don’t use them. Whatever’s in there will be silhouetted against your leg like Han Solo in carbonite.
How Your Shirts Should—and Shouldn’t—Fit
When it comes to shirts, start from the collar and work your way down. If you’re wearing a tie, make sure the shirt is designed to actually take one—it hurts to see a tie bursting out beneath an inadequate collar. And consider the shape and what it conveys. At best a high, broad, stiff collar suggests C-suite prowess, at worst Bond-villainy.
Michael Douglas’s Gordon Gekko in a shirt that we would advise avoiding.
I prefer a softer collar (without the little stiffeners) that cocoons the tie and nestles gently under the jacket. Drake’s does great soft collared shirts. The one golden rule, however, is that a collar’s tip should reach or sit just under the lapel of your jacket. Any gaps are to be avoided.
The collar is how you define the overall size of a shirt. If it’s too loose or too tight, the rest of the garment will probably follow suit. You should be able to fit a finger (and no more or less) between neck and collar when it’s buttoned-up.
I prefer a roomier, more “classic” cut shirt, and am always puzzled by guys that want their shirt to fit like a wetsuit, which I concede is flattering for those with the requisite physique, but needlessly snug. The likes of Thomas Pink and Suitsupply offer shirts with a tapered or “athletic” fit, which is broad at the top, narrow at the bottom, and stretchy in between. But to be honest, if a shirt fits, it will advertise your gains anyway.
Short-sleeve shirts are fine on their own, but never under a jacket.
How To Wear—and Not Wear—Accessories
Cufflinks are by no means essential (and most dress shirts will come with button cuffs), but if you must, keep them low-key. They are not a proxy for a sense of humour.
Belts can be tricky, too. Formerly, I would have advised against them altogether, recommending you just wear trousers that fit, or find a pair with side-adjusters. But I’ve changed my mind, and the right belt can really finish an otherwise uninspiring tailoring look, especially with separates. Try to find something with a bit of texture (maybe woven leather) with an interesting but inoffensive buckle. The western-style belts at Our Legacy are perfect. (And cos does something similar for a quarter of the price.)
Ties don’t need to be made of silk, but they do need to be thin-gauge, and neither skinny nor especially wide. The number of guys walking around with ties so thick they could double as scarves is alarming. And the thicker the tie, the thicker the knot will be, and thick knots are a no-no. There are a million fancy ways to tie your tie, but I have always trusted in the simple—an “oriental” knot—with a little dimple pinched into the top. In terms of simplicity, you could also go with the four-in-hand.
When it comes to shoes, consider proportion as much as style, colour, leather etc. If your trousers are wide and long, a little loafer might get dwarfed; if you trousers are short and slim, big chunky lace-ups will make you look like a golf club. Err on the side of caution and invest in a pair of derbies with a cleated sole, which are a good middle ground. Finally, I’m sorry, but tan dress shoes do not look good with anything. It is a diabolical colour and a scourge on society.
Pocket squares are fun for a wedding, or when you’re feeling especially fancy, but in general, I find them fussy. Especially those with cartoons or garish patterns. And don’t be precious about the shape, just shake it about and stuff it in your pocket. Anything too perfectly arranged looks over engineered.
