The Work Dress Dilemma

What to wear at work in 2019? The experts weigh in.

As Dylan said, “the times they are a’ changin’”. That goes for what to wear to work, too. When it comes to work dress, fashions come and go, and what was old is new again, from wide lapels and flared pants, to longer skirts to shorter skirts. Trends of fashion may change from year to year or decade to decade, but there is a real debate raging online and in the street about what’s appropriate to wear to work: is it still the traditional work uniform, the heels and dark power suits, or something less formal? How less formal? Could onesies to work really be a thing soon?

The Guardian has written a few thousand words recently about the shifting trends in work wear, which is having an affect on fashion design itself. When we start seeing politicians and business influencers at work in boho leisurewear, scuffed sneakers, scruffy beards, and worn jeans, looking more like dressed-down Silicon Valley start-up CEOs or my unemployed brother-in-law on a Tuesday, it begs the question, what can you wear to work? What should you wear?

Many organizations have their dress codes styled from the familiar, button-down past from Monday to Thursday, throwing in a casual Friday to loosen things up. Casual Friday usually means no tie, maybe jeans (if they look new or expensive), and a blazer. Open collars and jeans are supposed to be a freeing experience, showing staff the company knows how to relax (a bit), but there is still a Friday code, which doesn’t really scream personal freedom or self expression. And what are clothes if not a way we express ourselves as people? Some would rather never wear a tie or put on a business dress or high heels. Most people want to wear what makes them feel comfortable while looking good. But what is acceptable?

What if you showed up in a Yeezy workwear jumpsuit and sneakers without the laces? Some might applaud your forward fashion choices, while others might wonder why you didn’t get dressed for work. Wearing brand track pants and Adidas could be more acceptable in Los Angeles working in IT or entertainment than it would be working at a bank in Bonn or on Bond Street. So, does it really boil down to your industry and what’s still acceptable or not acceptable inside the four walls of tradition? How do you wear what you like while still respecting your company culture and the people you work with?

In the end you might be at the mercy of the corporate direction on workwear 9-5, but that shouldn’t stop you from finding ways to be comfortable in your own clothes at work. In the way not having a cell phone is a sign of “arrival” (some famous celebrities have eschewed owning a phone as a sign of their status), dressing down for work seems to be a sign of the times we might just have to get more comfortable with.

The Guardian, interviewing fashion influencer, Dan Rookwood, put it this way: “Dan Rookwood, formerly US editor of the menswear site Mr Porter, was once rarely seen without at least eight items of exquisite tailoring. He has recently taken a job as creative director at Nike, moved from New York to Portland, and adjusted his attire accordingly. ‘I now have the best wardrobe I’ve ever had – a proper walk-in wardrobe, where I can see all my clothes,’ he says. ‘But what it shows me is that I can’t wear the vast majority of it anymore. It’s all made-to-measure suits and shirts and ties and bench-made shoes that I just can’t see myself wearing outside the occasional wedding as the winds of style have changed. It’s like a museum.’

“Rookwood notes that the shift away from formal is industry wide. ‘Men’s fashion changes more slowly than women’s fashion. But if you look at what men were wearing in 2014 compared to 2019, it is markedly different. This is a big change. We’re just not as buttoned up as we were.’ The emphasis has moved from fine tailoring to luxury streetwear; from Milan and London to New York and Los Angeles; from Don Draper on the front of GQ to Kanye West on the sneaker site Highsnobiety. While in the past, a woven silk tie from Brioni sent a subtle cue about status, now it’s more likely to be limited-edition Yeezys. There is a whole new set of rules to fall foul of – as the billion-heir Kendall Roy discovers in the HBO TV series Succession when he fails to impress some prospective clients by wearing a pair of Lanvin calfskin sneakers to a meeting.”

Compared to previous generations, today’s careerists grew up with hip-hop, Missy Elliott, The Beastie Boys, grunge and other culture statements and street styles that have now come so far into the mainstream in ways that might make Brooks Brothers choke on a wingtip. Still, showing up to work in your pajamas might be a clothing choice too far, at least for now. But who knows what 2021 holds as the gig and freelance economy ramps up? When you don’t have to “go to work” to be at work, is there any fashion off limits? I would say yes, but I digress.

When it comes to work clothes for 2019, Pinterest puts together a list of search terms for major trends called the Pinterest 100 report, a kind of forecast of what people will be wearing based on search terms on the platform. Check it out, along with ways to shop for anything that strikes your fancy. Statement sneakers are in, along with snakeskin prints and bamboo bags. Who knows? You might start a new trend at work. Still, you might want to check with your boss before you wear Balenciaga’s Triple S sneakers to your next new business or board meeting. Unless the boss is wearing a pair.

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