The Most Stylish Guys You Know Are Getting Everything Tailored (Even T-shirts)

SOMETIMES WHEN Evan Glick, who’s cursed with a “fairly short torso,” tries on T-shirts in stores, “it just looks like I’m wearing a summer dress.” But if you spotted the 32-year-old Brooklyn data engineer in the street, you’d never mistake his top for a frock. Last summer, he began taking his tees and shorts to get tailored at his local wash and fold, for $15 a pop. Now everything fits snugly. “I don’t have to be disappointed with a too-big shirt,” he said.

A tailored T-shirt? Many men reserve tailoring for pricey, special-occasion suits. But in-the-know guys are turning to local, low-key tailors—with no hint of stuffy Savile Row—to tweak casual items from jeans to swim trunks. The move neatly solves an oft-ignored problem: Most off-the-rack clothes fit guys imperfectly. Men can easily look disheveled in too-long jeans or toothpick-armed in polos with gaping sleeves.

It’s Not Just for the Rich

For less money and effort than you’d think, a smarter-looking wardrobe awaits. Getting casual items tailored is “like a cheat code,” said Jermaine Crawford, 30, a Los Angeles actor who has all his jeans nipped at the waist because he finds belts bothersome.

But even men less hostile to belts are seeking help. Over the past two years, Yamil Vaca, founder of Manhattan’s Flatiron Tailor Shop, has noticed more guys bringing in casual items. Most commonly submitted for surgery: tees that billow, jeans that puddle on the floor and running shirts that run too roomy. Men with ill-fitting pajama sets also want his services. Vaca’s prices start at around $20 for abbreviating a pair of pants, and often just one, 5-minute fitting is required. Usually the tweaked item can be picked up in 24 hours if needed (the industry standard is about 3-7 days).

Less? Yep. More? Sure.

In many cases, said Vaca, guys with newly rigorous workout regimens want more-fitted clothes to better flaunt their physiques. But a good tailor can magically make items bigger too. A client of New York personal stylist Turner Allen recently lamented the too-short sleeves on a chore jacket. So a clever tailor stole fabric from its back to lengthen them. Allen doubts most men “would know you could do that, but it made all the difference.”

One particularly egregious issue any good tailor can easily fix? Overly roomy shirt sleeves that make men’s arms look spindly. L.A. style consultant Andrew Weitz said he’s always having clients’ sleeves narrowed. Recently, one guy’s knit polo with short but cavernous sleeves got the treatment and suddenly he looked like he’d been eating his spinach. “Now it hugs his biceps and gives him that [defined] arm shape,” said Weitz.

Weitz also finds swim shorts often disappoint off-the-rack. “A lot of guys feel they’re a little too long,” he said, so they’ll get an inch or so snipped off. Flashing more thigh gives the illusion of longer, leaner legs, he said. Swim shorts should hit at about mid-quad, he added.

L.A. stylist Ugo Mozie seeks out tailoring to alter garments more dramatically. He once tasked his tailor with transforming a women’s trench-coat dress into a men’s jacket. For less statuesque clients, he has shirts, T-shirts and tank tops all hewed to right below the waist. That length works on shorter guys, said Mozie—it suggests “a longer frame.”

How to Ease In Gradually

Whether you’re after a startling chop or a subtle tweak, you’ll need a trustworthy tailor. Beyond checking reviews, experts suggest first testing a new tailor with an easy alteration, like hemming some pants. “If you’re happy with that, you can take a shirt to be slimmed, and then a blazer to be altered,” said Allen. “Start small and go from there.” Snip by snip, let the style upgrade begin.

They Got What Tailored?

Insiders report on some of the unlikely items that men have been getting tweaked

1. Sportswear

Billowing running tops and Lycra cycling tights in need of extra tightening are a common sight at Manhattan’s Flatiron Tailor Shop, said Vaca.

2. Swimwear

Lots of guys find swim trunks a little too long off-the-rack, said Weitz. He’ll ask a tailor to slice about an inch off. Result: Guys’ legs look longer (and they can sun their thighs).

3. Casual slacks

Mozie’s hot tip to achieve a louche pant cut? Buy a wide-leg pair in a slightly too-big size and get the waist and upper thigh taken in. This, he said, achieves the ideal relaxed shape.

4. Pajamas

Vaca has been seeing more sleepwear drift into his shop—especially pajama sets that men want either lengthened or trimmed. “I guess guys want to feel stylish right before they go to bed.”

5. Workwear

Allen recently had the sleeves of a chore jacket lengthened for a long-limbed client whose wrists were awkwardly sticking out.

6. Knitwear

When a knit polo or a sweater is too voluminous, Weitz will have a tailor “take in the body.” Even if it’s meant to be an oversize design, too many guys end up swimming in their sweaters, he said. It shouldn’t wear you, he added.

What’s more important than being a good employee right now? Looking like a good employee in the eyes of AI productivity trackers that more managers are using to evaluate their teams.

Employee-monitoring systems are especially popular at tech companies and are also used by other white-collar firms that want to probe how people spend company time. The scary thing: You might not even know you’re being watched because many states don’t require disclosure.

Metrics can include performance data that is undoubtedly relevant, such as sales results. But it also can employ dubious proxies like keyboard strokes and how often your computer screen goes into sleep mode.

We generally accepted, or at least understood, heightened surveillance during the work-from-home era. Back then it seemed reasonable for bosses to keep tabs on employees they couldn’t see.

Yet the oversight has only escalated, and tensions are rising, too.

A group of former Meta Platforms employees alleges in a lawsuit that the company used a “constellation of internal artificial-intelligence systems” when it began laying off about 10% of its workforce in May. Meta says humans make termination calls.

However that case shakes out, a couple of things are clear. Companies eager to gauge which employees are locked in now have sophisticated AI monitoring systems at their disposal. And they believe they have leverage in a tepid labor market.

So while we may chafe at having our worth reduced to numbers on the boss’s productivity dashboard, we have to play the game as it’s being played. Here are some tips, based on conversations with people who make employee monitoring systems—and others who game the systems.

Be meticulous about your calendar

Calendar integration is one way that productivity trackers have gotten more advanced and, ostensibly, fairer.

Let’s say you make an old-fashioned phone call or attend an in-person meeting. Your Outlook or Slack status may switch to “away,” making you appear as inactive as if you were taking an extended coffee break.

Employee monitors like one made by a company called Insightful cross-check your online status with your calendar to see whether there is a valid reason for your apparent inactivity. If that call or meeting is on your schedule, then the system will recognize that you are busy offline. If nothing is on the books, it could look like you’re slacking off.

Hit the activity sweet spot, around 80%

Let’s not go any further without addressing the underlying question: How much downtime is permissible during the workday? After all, people have been scared to let managers see anything non-work-related on their screens since personal computers first arrived in offices.

No one knows this better than Roger Wagner, who is widely credited with creating the first “boss button” in the early 1980s. He designed a keyboard shortcut to instantly display a spreadsheet if the boss walked by your cubicle while you were playing a computer game. Boss buttons have been features of countless diversions since. (I confess to using one built into a March Madness streaming app.)

Wagner, the founder of computer-education company 1010 Technologies, says his original design was a joke—more of a commentary on overbearing managers than a cover for lazy employees. Good bosses understand workers need mental breaks throughout the day, he says.

This matches what I heard from Insightful Chief Executive Ivan Petrovic. He says customers that use his company’s workforce-management platform don’t expect employees to stay on task 100% of the time.

“On average companies are aiming for 60% to 80% of your time being utilized for work during the day,” he says.

Go ahead and exhale. It’s probably OK to watch an occasional YouTube video at your desk.

And if you’re going to artificially inflate your activity level, be careful. Hitting 90% could look suspicious.

Get physical

So don’t leave your mouse jiggler on all day. Choose the right one if you must resort to shenanigans.

There are lots of software applications that mimic the movements of a computer mouse, so you can appear to be working while away from your desk. There are also devices that plug into computer ports and do the same thing.

Corporate cybersecurity systems increasingly block these apps and devices, and productivity trackers claim to be able to detect them. But some workers swear by mouse docks, like one made by Tech8 USA, that keep cursors moving. The company originally made mouse-moving software but now focuses on physical jigglers.

“People are drawn to mechanical solutions because they’re so simple and don’t require software,” says Tech8 Marketing Director Sam Matthews. “As monitoring technology becomes more sophisticated, that distinction has become even more relevant.”

Use AI, but not too much

Another popular metric for employee-monitoring systems is AI usage. Companies want to know who is embracing new tools, and it can be tempting to think more is better.

“There’s a performative aspect where employees overblow their usage of AI so that they appear relevant in the organization,” says Andrea Derler, principal researcher at Visier, which helps companies track and analyze employee work habits.

In a recent Visier survey of 1,000 U.S. workers, 48% admitted to exaggerating their AI usage.

This is already an outdated strategy. Using AI for everything used to score points for experimentation. Now it can seem wasteful because many companies are watching AI token spending more carefully.

Look, productivity theater has always been part of work. Most of us aren’t trying to cheat the system, but expectations are changing so quickly that we need to be savvy about what the latest employee trackers are looking for.

Sometimes it takes a little gamesmanship to get full credit for our contributions.