Why Successful Men Often Dress Badly and Look Burned Out

Photo:  Pawel Jaszczuk

Recently, I watched a video featuring someone I used to know—a gentleman in his early 40s, now an executive director at one of the biggest creative companies in the world. He’s undoubtedly successful, with a great salary and expertise that earns him respect within his professional network. In the video, he was discussing some insights from his industry. But, despite my best efforts, I couldn’t focus on his message because I was distracted by his appearance.

Once a strikingly handsome man, he looked extremely tired, with dark circles under his eyes, a sad demeanor, and a hairstyle that raised some questions. But it was his outfit that caught my attention—a white t-shirt and baggy jeans—which wasn’t doing him any favors either. The t-shirt’s oversized fit made him look like he had a belly (which he doesn’t, as he’s slim and tall), and the baggy jeans hid his well-proportioned figure.

I couldn’t stop thinking about the video. It was a reminder of how overworked, ambitious professionals—often single men in high-power roles—sometimes let their appearance take a backseat. This isn’t a critique for critique’s sake; the issue is that his look overshadowed the important points he was trying to convey. For someone representing their company in public, appearance matters because it affects how well people receive your message.

In my 14+ years in the corporate world, I’ve seen this pattern frequently. Overworked men, often without much work-life balance, seem to spend all their time in the office. Their social lives might involve occasional outings, some alcohol, or even drugs, but there’s a clear lack of grounding (female) energy in their lives. I’m not a psychologist (however, my Kindle is currently filled only with books on psychology and business), but I can’t help wondering: Why do men who earn so much often neglect their appearance?

I’m not even diving into a big philosophical discussion about the importance of fashion. But let’s face it: no matter what you do, you can’t walk out naked (unless you want a free ride to a psych ward). You will spend money on clothes at some point—it’s just a matter of how and where. And for those who dismiss fashion as trivial, here’s a fact: the global apparel market is worth $1.79 trillion, accounting for 1.6% of the world’s GDP. Fashion is clearly more than just fluff.

On top of that, research from Princeton University shows people judge your competence based on your clothing in less than a second. Is it fair? No, but that’s how human brains work. First impressions matter, especially in professional settings. Over the past few years, I’ve paid more attention to men’s fashion and realized how underserved they are. Walk into most stores, and you’ll see men’s sections tucked away in a corner, occupying a fraction of the space compared to women’s.

This lack of focus might explain why many men don’t put much effort into their wardrobe. It’s not always that they don’t care—it’s that the industry doesn’t cater to them. In Madrid, a city of 3.4 million, I found only five stores solely devoted to men’s fashion. And only in these stores did I notice attentive staff offering real style advice.

Another reason I focus on men’s fashion is the number of men who’ve approached me for advice—not just on style but on life in general. It surprised me to learn how many men in their late 30s and early 40s lack close male friends. The topics they share are often deeply personal, and it feels like they need retreats or spaces to reconnect with themselves.

When it comes to fashion, even those who want to dress better feel insecure, fearing judgment from their peers. Despite being confident professionals, they hesitate to stand out in their personal style. This is why I’ve created a few simple but powerful fashion mood boards tailored to taller, slimmer, or athletic men. These looks are sharp, emphasize their best features, and are easy to put together. I used clothes from popular fashion brands to create complete looks, making it easier than ever for you to put together the perfect outfit!

COS Total Look

Trousers, Sweater, T-shirt, Scarf, Beanie, Jacket 

Massimo Dutti Total Look

Turtleneck, Jeans, Shoes, Blazer, Belt, Backpack

How about you? What do you think the industry could change to make fashion more accessible and enjoyable for men? And how do you approach your own style choices?