I still have a hard time wearing shorts to work.

This is ridiculous, I know. I am the style director of Women’s Wear Daily. I have spent more than two decades looking at, writing about, styling and selecting images of men in shorts. I have watched the silhouette become shorter and shorter, from the runway to the street. 

I have spent most of my life strongly questioning the rules about what men are supposed to wear — and yet, when it comes to wearing shorts in the office, I hesitate.

I suppose I should start with my father. He was an incredibly well-dressed man, but a very traditional one. He had unspoken but clear style rules, and one of them was: Shorts were for the countryside, never the city.

You could wear them on holiday, in a summer town, or if you were playing tennis — a must at my house. But you did not walk around a city in shorts. And you certainly did not go to work in them.

I grew up in Spain in the 1990s surrounded by this kind of thinking. There was a very specific idea of what a man should look like. Khakis. Polos. Neutral and dark colors only. Don’t stand out too much. Don’t be too different. Don’t be unique. 

I found it suffocating. There was a social claustrophobia to it, a sense that so much of your life had already been decided for you: how you should behave, what you should want and of course how you should dress. And the fashion claustrophobia was almost worse. I couldn’t understand why everyone had to look the same.

So, you would think I would have liberated myself from all those rules by now. And yet, somewhere in the back of my mind, my father is still there.

Queer Culture Is Redefining Dress Codes, So Why Am I Still Reluctant?

When I went to Fire Island Pines right after the pandemic, I was surrounded by men wearing the shortest shorts imaginable. You know desperate times, desperate shorts. There were tiny shorts, short shorts, shorts that barely seemed to qualify as shorts. At first, I thought: How do you wear that outside the queer dimension? Then I realized I was looking at a much bigger cultural shift.

When I was younger, the idealized gay male body seemed to be about the torso. Big arms and big chest were the focus. The body was built upward. But with Gen Z, the focus has shifted downward. The legs have become the new object of obsession: worked out, overdeveloped, displayed and, increasingly, exposed. If the legs are the new erogenous zone, then of course the shorts are getting shorter.

What fascinated me was how quickly something that seemed so specific to queer culture began to move outward. The queer world has always been a place of influence — fashion insiders inhabit the space and pull from it. Things might initially look outrageous, overly sensual or simply strange, but usually, the outside world catches up. 

That is what I watched happen with the short short, meaning 3 inches or less. Once the shortest shorts became the norm in queer spaces, they appeared on runways. Then celebrities. Paul Mescal famously wore extremely short shorts to a Gucci show. The athletic nylon short of the 1980s came back, now paired with dress shirts, jackets, socks and loafers. What once looked like something you wore to play tennis or soccer was suddenly being styled as fashion. 

Still, I didn’t wear shorts to work during the Paris shows this June, when the heat was practically apocalyptic. 

It was unbelievably hot. There was little or no air conditioning in some venues, and some shows were hosted outside in 100-degree weather. We were all sweating through our clothes. At a certain point, dressing for fashion became secondary to dressing for survival.

Everyone around me seemed to be wearing shorts. And not just any shorts. The shortest shorts I had seen in years. Athletic shorts. Nylon shorts. Shorts with dress shirts. Shorts with jackets. Shorts with socks and loafers or the ultra-thin lace-up shoe, or the Celine shoe as it is now called. The whole thing had become completely normal in the fashion crowd. 

I personally had options. Trust me. I travel with shorts. Short shorts, Bermuda shorts, pleated dress shorts, high-waisted shorts. I have tried them all on, but I still couldn’t do it.

Street style is one of the games my ego plays, so I wore sleeveless blazers and vests. My look was not even particularly provocative. For me, it was a very chic option. I channeled the early 1990s Armani Aldo Fallai Morocco ads: a beige vest over pleated linen trousers. I thought I was making the more sophisticated choice.

And yet the reaction was extraordinary. “Look at those arms Alex!” I heard several times. I thought: “Wait a minute. I’m wearing a sleeveless look, but these people are wearing shorts that are 3 inches long at best.” So I started asking people what they thought was more acceptable: short shorts or sleeveless? I asked writers, reporters, retailers, fashion editors, people sitting in the front row. Almost everyone gave me the same answer: short shorts. That was the moment I realized how completely the rules had changed around me. In the fashion world, short shorts, or any shorts for that matter, are no longer necessarily shocking. In some creative circles, they are practically another day at the office. When it is hot in the city, legs are primetime and the sleeveless man, apparently, is more provocative. Who knew?

The Corporate Conundrum 

But outside that world, the rules for any kind of shorts for the office are different. In corporate America, I suspect seeing a man in shorts will still raise eyebrows for the near future. In finance, banking, law, insurance — you know the more conventional and extremely suffocating parts of the white-collar world — shorts still carry the stigma that they lack professionalism and somehow convey a lack of competence and maturity. Perhaps that’s the real reason men have such a difficult time wearing them to work.

The dot-com boom made jeans and T-shirts acceptable in offices that once demanded suits. Casual Fridays helped normalize denim. Premium denim followed. Somehow, we have decided that a man can be perfectly competent in sneakers, jeans and even a T-shirt, but the moment he shows his knees, his authority becomes questionable. That seems increasingly absurd. Many articles have been written about how things are changing. In Tokyo, men are wearing dress shorts to the office it seems. Will this happen at home in the States? 

I don’t think so, but the climate may force the issue. During the Paris shows, the question wasn’t whether shorts looked professional. It was whether you could physically survive the day in trousers.

And then there is the younger generation, which seems much less interested in the idea that professionalism has to look a certain way. To them, a suit can be just as imposing, restrictive and old-fashioned as a pair of shorts might look unserious to an older generation. Trust me, I get that.

The question becomes: What exactly are we dressing for? Competence? Comfort? Or conformity? 

I personally never really dress for the weather when I can help it, but I have spent most of my life rebelling against conformity. I don’t believe in arbitrary fashion rules. I find the people who declare that something is simply “unacceptable for menswear” almost unbearable. That old-boy network meets high-horse behavior feels very “loserville.”

For example, I don’t care about the idea that white jeans shouldn’t be worn after Labor Day. In fact, I only wear white jeans in the winter, they look better to me. So why do I still hesitate when it comes to shorts? To be honest, shorts make me feel vulnerable in a way that trousers don’t. Perhaps it’s the silhouette. I love the line of a long trouser. I like the authority of it. Somehow, it seems I was always part of the problem. And there it is my own unsolved traditionalism, sneaking back in through the side door.

One thing for sure is that if dress shorts become part of corporate dressing, a whole new “can of worms” will come with it. What shoe do you wear? What sock? How much leg hair is acceptable? Does the leg need to be groomed? What about tattoos? These can easily become a minefield. 

We have spent decades telling men that they need to follow rules because, apparently, without rules, some men don’t know what to do. 

I do know what to do. Fashion is my job. But here I am, standing in front of my closet, holding a pair of shorts, still wondering if I should wear them to work.

Maybe that’s the strange thing about clothes. We think we are choosing them but maybe they are choosing us. Sometimes a pair of shorts isn’t just a pair of shorts. It’s your childhood. It’s your father. It’s the idea of what a man is supposed to look like. 

It’s the fear of looking too weak, too casual, too exposed, too feminine or just plain too much. Or maybe it’s simply the fear of breaking one last rule.