Menswear Inches Forward

When John F Kennedy was elected president in 1960, it was an exciting time for the country. Young and handsome, with a pouf of great hair, Kennedy signified the new vitality and promise of America. With a beautiful wife and celebrity appeal never matched in an elected leader, he had appeal in every way, for every aspect of menswear, except one. He didn’t like to wear a hat.

The hat industry was beside itself. Here was the leader of the free world, seen by millions, who was rarely seen wearing a hat. It may be a myth that Kennedy was single-handedly responsible for the hat’s demise. Some say it was the movement away from public transportation to automobiles that was the true cause (it is, after all, easier to wear a hat on a bus or train than riding a car). Whatever the true cause, let’s just say Kennedy’s timing for hat sellers couldn’t have been worse.

Tie One On, Or Not

In the 21st century we have the same issue with men’s neckwear. Obama has famously turned the Oval Office into a tie-optional zone. It is the same in the Canadian government; sometimes Prime Minister Justin Trudeau doesn’t even wear a shirt. Fewer banks are requiring ties at work, and the environment has changed so that not wearing one doesn’t mean you don’t have power. If you’re a Bitcoin banker, you don’t even need to wear pants.

At hedge funds the standard of dress has been Dockers with a polar fleece vest (usually emblazoned with a conference just attended). I call it the Connecticut tuxedo. Silicon Valley has its own look: wear pretty much anything, given that they pay the hedge fund executives’ salaries.

According to NPD, neckwear sales in the U.S. peaked at $1.8 billion in 1995. By 2009, the figure had fallen to $418 million. By the mid- to late ‘90s, technology was starting its robust climb to becoming a leading force in the economy. The workplace was changing. Pizza boxes doubled as filing cabinets, water coolers were replaced by cases of Red Bull. As with men’s dress in Kennedy’s era, which saw the rise of automobile ownership, today’s digital technology is affecting how men dress.

The Long Entrepreneurial Tail

The Small Business Administration’s Office of Advocacy says that 99 percent of U.S. companies have fewer than 500 workers, and 86 percent have fewer than 20 employees. Small firms accounted for 63 percent of the net new jobs created between 1993 and mid-2013, or 14 million of the nearly 23 million net new jobs. Since the recession’s slow motion end in mid-2013, small firms accounted for 60 percent of net new jobs. Small firms with 20 to 499 employees led job creation.

The rise of entrepreneurship affects workplace style. Entrepreneurship has been growing propelled by millennials, who represent the largest workforce in the country as well as the nation’s largest living generation, at 74.5 million. Add Generation Z (those born after 1995) at 72.8 million, who are starting to enter the workforce now, and are more likely to follow a style similar to their sibling millennials. Now you’ve got not one, but two generations representing almost 50 percent of the U.S. population who are somewhat unlikely to wear a tie. By 2020, Gen Z is projected to represent 40 percent of all consumer spending.

It’s pretty clear what is happening here. The confluence of technology and the explosion of small businesses are changing how men dress. The rise of the entrepreneurial nature of the workplace is allowing for a new image. Look at the explosive growth of shared work environments like WeWork, a fast growing chain of offices that prides itself on giving free beer all day long. These spaces have their own distinct looks and pride themselves on a casual environment.

So Where Is Menswear Headed?

I compare what is happening now to how Starbucks created a third place between work and home. We need a wardrobe that matches that sentiment. Work is becoming less structured and that reflects how you need to represent yourself in it. I’m not talking about a five-day-a-week “Casual Friday,” but a more refined example of distinct, but professional. And yes, it may involve wearing ties sometimes. In full disclosure, my company makes ties and I wear them all the time.

Our tie business is strong, the more contemporary the better. Our white and blue shirt sales are strong and always will be, but at the same time, men are wearing mini-check shirts and micro patterns. And you don’t need to wear a tie with those styles, Men are slowly adopting a more contemporary look in the workplace as the “work” is being redefined.

I also see the same trend happening in tailored clothing with men bringing more color and pattern into their suits. Yes, the classics are still needed: black, gray and navy; but if you dress a basic suit with a patterned shirt, you get a fresh look. The days of the IBM computer salesmen are gone. If you want to sell the future, you should look like the future.

I live in New York, which can skew anyone’s perspective. But it’s happening in all of the markets we sell to, in every part of the country. American style is also being influenced by the internet, allowing men everywhere to see global trends. Look at the pages of GQ, the bible of men’s style— and a magazine that I think is the best in its class— and you can see what is happening. I think there is nothing better looking than a guy in a suit with a tie that gets attention. And I promote it wholeheartedly. If we go back to Kennedy and the fact that it’s hard to wear a hat in a car, and the unanticipated influence a presidency can have on style, I have two thoughts.

Elon Musk needs to raise the roof of the Tesla six inches and we can bring hats back.

And would you really want a president who wears his ties that droop four inches below his waist? Honestly, I’d rather wear a pantsuit.