THE JOURNAL
In 2019, shortly before the pandemic would revolutionise the labour market with work-from-home arrangements, the top-brass at Goldman Sachs sent out a firm-wide email announcing a new dress code. In the memo, CEO Mr David Solomon recognised that modern workplaces are more casual and, in an effort to recruit young talent, the white-shoe investment bank was going to join the Silicon Valley crowd by allowing its 36,000 employees to shed their coats and ties for a more casual uniform.
What was supposed to replace dark worsted suits and banker striped shirts was not clear. The company’s management simply suggested that employees “exercise good judgement”. Still, as one Goldman Sachs banker told GQ, “All the men are psyched.”
The coat-and-tie look has been dying a slow, anguished death since the end of WWII. The slippery slope started as a gentle decline in the 1960s, a period that coincided and overlapped with the decade’s culture wars. Establishment types wore the suit; anti-establishment types took to white T-shirts, leather jackets and jeans.
After the Casual Friday movement of the 1990s and rise of tech bros in the early 2000s, the suit was all but dead, surviving only in the corners of finance, law, government, and television newscasting. When Goldman Sachs sent The Memo, it was a sign that even in those sectors, the suit was losing its shine.
“If outdressing your coworkers makes you feel uneasy, there’s a simple solution: go to a nice restaurant”
This has posed a problem for men who love tailoring. If everyone at the office is dressed down, there are simply too many opportunities for embarrassing questions about your appearance.
The good news is that most people are not as judgmental as we assume. In psychology, the term “spotlight effect” refers to our tendency to believe we’re being noticed more than we are. We experience the world as the “main character”, but forget that we are not the centre of other people’s worlds (they are, like us, preoccupied with themselves).
Emotions such as anxiety can “anchor” how we read others around us, even if we’re not privy to their thoughts. So, when we do something atypical – such as wearing a suit when others are not – innocent questions like, “Why are you so dressed up?” can feel can carry more than their fair share of weight. As it turns out, most people are just saying you look nice (without actually saying it).
The easiest way to incorporate tailoring into your life is to simply do it. But if you’re not wild about sporting a full suit to work every day, break it into pieces. Most men can wear at least a sport coat to the office without feeling self-conscious (or looking out of place), even if others are dressed more casually. A sport coat pairs nicely with a light-blue button-down shirt, tan chinos, or even the right pair of jeans to make the outfit look more relaxed.
If outdressing your coworkers still makes you feel uneasy, there’s a simple solution: go to a nice restaurant. By “nice restaurant,” we don’t mean three-star Michelin-rated establishments where you pay a month’s rent for an appetiser. Think something a little more upscale than where you go for lunch.
“Dressing up gives a sense of occasion. People need that now and then to keep things lively”
I got this idea many years ago from my friend Mr Andy Poupart, who lives in Silicon Valley, the epicentre of California’s dressed-down business culture. He and his wife, Ms Michèle Free, have a weekly tradition they playfully call “Formal Friday”, where they dress to the nines – he in a tuxedo or dinner jacket, she in a dress – for the quotidian act of getting dinner.
“If my wife and I go out in the evening, we ‘dress up’ because we want to,” he told me. “It bothers us not at all if we are dressed more formally than everyone around us. We dress for ourselves and each other, and that’s it. We have reached a point in our lives where it is time to be ourselves. If we find ourselves in a place where everyone else is in jeans, so be it.”
Mr Jeff Hilliard, senior director of limited editions at Hodinkee, also wears a suit for dinner, partly to make ordinary events seem more special. Before moving into the watch world, Hilliard worked in tailoring, in a job for which he wore a suit on a daily basis.
“Dressing up gives a sense of occasion,” Hilliard says. “People need that now and then to keep things lively. Besides work events or special occasions, going out to dinner is one of the few times a situation may call for something a little more formal.”
For him, this means wearing a suit with a casual element, such as a snap-button denim western shirt, or replacing the suit with a heavily textured sport coat. If he needs to go a little more casual in the winter months, he’ll wear a cashmere sweater with a tailored topcoat.
If you’re just starting to incorporate tailoring into your wardrobe, you can find ways to make the clothes feel comfortable and natural by knowing how to slide down the formality spectrum. Poupart is unique in that he’ll wear a tuxedo to dinner (for him, if there’s white tablecloth, the setting is dinner jacket-worthy). But that’s on the highest level of formality, and there are many options for something a little more casual.
“Consider a suit that won’t make you feel like you’re heading into a job interview”
First consider a suit that won’t make you feel like you’re heading into a job interview. In other words, forgo the slick navy or grey worsteds and play with colour, fibre and texture. Try a wool-mohair blend, which has a subtle sheen that looks tremendous under artificial light (think: dim bars and restaurants). In the summer, a tobacco linen suit is ideal for dining al fresco; in the winter, a grey flannel double-breasted look will do nicely.
Go even further by selecting a more casual top, such as a long-sleeve polo shirt, fine merino crewneck sweater or rollneck in place of the classic white poplin dress shirt. While black plain-toe Oxfords are always the most sophisticated and elegant evening footwear choice, you can also go for slightly more casual shoes, such as brown penny loafers or Derby shoes, black tassel loafers, or brown suede chukkas.
If a full suit feels too formal, start with a navy sport coat. You can wear this with tan tropical wool trousers in the summer, whipcord in the winter or dress it down further with tan single-needle chinos, or slim denim jeans. A navy sport coat has a smart but slightly casual Ivy Style sensibility when paired with light-blue Oxford button-downs and penny loafers, and picks up some cool cred from the right T-shirt. (A plain white tee made from a fine cotton always works, although you can also go for a graphic – something from a Japanese brand or maybe vintage.)
But, really, the best place to start is with dinner. Grab a couple of friends willing to dress up – I promise many will jump at the invitation – and make it a weekly or monthly tradition. Going out for a nice meal will give you something to look forward to at the end of every week – and an excuse to wear some tailoring.