Why do divorced guys dress like that? 

In this world, there are divorced men (fact) and men who are the most divorced (derogatory). 

Men who marry will be divorced or they won’t. Men can also divorce and remarry, or divorce and remarry and divorce again, over and over, as many times as their hearts desire. According to the Census Bureau, roughly 33 percent of straight men who have ever been married have also been divorced, and the older a man gets, the more likely it is he will have been divorced at some point. 

But that’s not what people mean when they call a man the most divorced. In describing men this way, wordsmiths have crafted a critical spectrum to reflect their dismay, concern, disgust, chagrin, and often sexual aversion at a specific hypermasculinity shared by high-profile divorced guys. Journalist and critic Hunter Harris has a recurring bit about “the most divorced” men, naming Kanye West, Elon Musk, Ben Affleck, Joe Jonas, and Jeff Bezos as examples. It’s a distinction that’s not about the number of times a man’s marriages have dissolved but rather the severity of his resulting aura and how he presents himself. 

An example: Musk is divorced, but he is the most divorced when he’s posting a picture of guns, cans of caffeine-free Diet Coke, and a small reprint of George Washington crossing the Delaware River on his nightstand. 

While behavior varies, the aesthetic of the most divorced man remains remarkably consistent, and that is tight, sometimes shiny, clothes and a starter pack of flashy accessories.  

The derision this look receives raises an important question: If the most divorced man is to be avoided, then why do certain men, especially famous ones, continue to dress so divorced? Why is the most divorced guy aesthetic so popular, even when the most divorced guy persona is not? 

What is a man and why is he so divorced?

To be clear, it’s not that all divorced men wear a certain set of clothes; it’s that some newly single straight guys dress and accessorize in a way that eroticizes a violently loveless persona. Usually it involves leather, a lot of black, and a snug fit. Just as important are the add-ons: aviators, a bracelet or other jewelry like an expensive watch, cigars and a fancy lighter, and less appreciated trimmings like guns and cryptocurrency. It’s as though these men may be asked to shoot something and then light it on fire, all in a designer T-shirt.  

“It’s about the kind of middle-aged guy that’s hitting the club in a certain kind of jacket, in a certain kind of shirt and certain kind of jeans and shoes, and he just kind of looks like a guy who’s trying to appeal to a 22-year-old,” said Derek Guy. Guy, the founder of Die, Workwear!, has also become a celebrity on X for his expertise in menswear. “And it’s not just like, going to Target, for example. They’re going to a little bit more of an upscale store, but at the same time, they’re probably buying into trends that are 10 to 20 years old, and they haven’t kept up with how trends and things have moved.” 

Guy explained that these fits are even more glaring now that actual young people are wearing oversized or baggier clothing. But his example isn’t that far off from divorced dudes from previous generations trying to look younger — nor is it that far off from what’d we previously label as midlife-crisis chic (leather jackets, hair dye and/or a toupee, a convertible). 

All these strong aesthetic choices mean that the most divorced men don’t actually have to be divorced at all. What’s key here is a mood, a feeling, a state of existence that most of us want no part of. Being able to clock it from a distance — from a phone screen, preferably — becomes a shared relief. The beauty of the most divorced guy archetype is that he is rarely, if ever, in the same room as us but, at the same time, is ubiquitous, like a boogeyman who loves Las Vegas nightlife. 

While we’re likely pulling these ideas from what we see in the media of very rich and powerful celebrities like Musk, Bezos, and Affleck, who have access to stylists and social media managers — Guy encourages us to think about the way we project meaning onto fashion, and onto the men, famous or regular, wearing these clothes. On one level, a man dressing in uber-divorced men’s garb may be clinging to an expression of masculinity. But the people making this judgment have also created a narrative in their heads about what kind of person he is. 

Guy worries that as this spreads to regular guys who want to experiment in their fashion, divorced or not, it ends up having a chilling effect. “I’m careful with the term”— divorced guy — “because I always want to make it easier for guys to get into what I consider a hobby,” Guy said. “And using the term can make guys worried [about fashion] and just puts another obstacle, another fear, on the road to them finding something that I think can be very fulfilling.” 

The delineation is in the intent and awareness. As Guy points out, some guys buy a Rolex because they want you to think certain things about them, their power, their wealth, their manhood; other guys just really like watches.  

With this in mind, it seems that what unifies the divorced guy style is that they wear their masculinity as a shield. They want you to think they’re too manly to be contained, which they illustrate with choices everyone knows no woman had a hand in. What they might not have done, however, is reconcile the husband they used to be with the man they’re becoming now.

Why don’t men simply not dress divorced?

Few people knowingly pick out a visually unpleasant outfit because they think it’s horrible. Deliberately doing that would be clown behavior. There’s some disconnect there, a gulf between what one person thinks looks good and what marks them to others as an insidious archetype. That disconnect might be reflecting something deeper.

“There’s one thing that I am really aware of is that there are so many resources out there for divorced women and women going through divorce. And I don’t think there’s the same kind of support for men,” said Alexandra Solomon, a psychologist specializing in relationships. She explained that because of this support, women have a better understanding of what life post-divorce looks like, whereas men — billionaires and non-billionaires alike — don’t have that same kind of clarity and backing. 

“There really is a dearth of community support and conversation about how to help men transition out of marriage in a way that honors the profound shift in identity that occurs when you come out of a divorce.”  

But how does that loss and confusion turn into purchasing a horrific shirt? Does a lack of resources compel a man to post pictures of beers and guns for clout? Are men just aesthetically violent sleeper agents waiting for activation, and is that trigger divorce? 

There are myriad steps between a split and buying an outfit to reflect said split. Solomon explained that what lives between — or, crucially, fails to — is a psychological term called “self-concept clarity.” Essentially, this is how human beings frame our own identity and how well we think we know ourselves. She said studies have shown that when people go through emotional breakups, their sense of self shatters. 

“We don’t need to laugh at them and we don’t need to pity them,” Solomon said of men who make bold fashion choices following a breakup. “But we could be curious about what it is they’re displaying. Reclamation? Transition? A new identity? We’re all generally clunky about all those things.” 

Ego death coupled with a lack of emotional support may be why certain men seek out the divorced guy aesthetic. Hypermasculine clothes and other external markers help them self-identify or graft an idea of what they perceive being a single man to be onto who they already are. Divorced guy aesthetic is, often, an impression of a single man — a caricature of another caricature, but absent irony or self-awareness. And maybe it’s all in an attempt to show the world they’re doing okay. 

It’s the sexual implication of these signifiers that can be unnerving to others. There’s a sense that they belong to an aggressively on-the-prowl bachelor. It is true that people should dress in ways they find empowering, and a leather cuff is not in and of itself an unwanted sexual overture. But it’s hard to ignore the carnal hope that seems implicit to its wearer.

Because the most divorced guy vibe is so adjacent to to tenets of toxic masculinity — aggression, violence, sexism, compulsory heterosexuality — the yuck it elicits feels similar too. There’s something desperately insecure about holding on to outdated masculine norms. Expressing our ick reflects our own changing ideas about how men should act and present themselves. 

“We always should investigate our ew. Our ew says as much about us, just as much as it says about the other person,” Solomon said. “Our ews are always worthy of our investigation.”

That knee-jerk, shudder reaction is a problem when divorced guys seemingly need all the empathy they can get. Community, especially among men who have regained their self-conception after a split and those still in process, might well be the answer. After all, being divorced isn’t the worst thing — unless it’s from reality.