When Clothes Matter And When They Don't (Even For Guys)

From the words of our CEO, Blake Smith: 

When we first started Cladwell, it kind of messed up my personal relationship with clothing. Because I ran a “fashion” company, my clothes became the center of attention. People would comment on my style more than ever or apologize for feeling underdressed around me. I totally get that people were just trying to connect with the industry I was in, but a weird pressure developed that I had to live up to the persona of a fashion startup founder. 

Feeling the pressure, I started trying harder and dressing up more, because I knew that people would be analyzing and commenting. My wife (who does not work at Cladwell) felt it, too. When she hung out with her friends, they’d start asking her about her wardrobe or what she was wearing. Some of it was just natural, but at a certain point it started to get weird.

I remember this one time my son and I were going to a baseball game and I googled “how to dress well to a baseball game.” I wore a collared button down and loafers to a baseball game—a freaking baseball game. I remember walking around and seeing all these people dressed comfortably on a hot day, as I’m sweating because I needed to “represent” Cladwell. It was really lame. Something needed to change.

After listening to thousands of men who use Cladwell, I found that I was not alone. There seems to be a weird binary phenomenon when it comes to men’s clothing; men either slot into one of these two categories:

A) Clothes Always Matter:

Picture Don Draper for Mad Men. This hipster wakes up with his hair combed, clean white tee shirt, and always well groomed. Whether it is chores around the house, a BBQ, baseball game, etc., this guy knows that his clothes communicate who he is, and he is always on. In my experience, this is where most of the fashion industry lives.


B) Clothes Never Matter:

This can range from the Homer Simpson persona of  “I don’t care” to the Mark Zuckerberg type—“I’ve got more important things on my mind." 

If you work with humans at all, at some point you realize that B can’t be true. Your clothes matter in certain circumstances. So—much like the binary approach to politics—if you aren’t team B, then you must be team A. Suddenly your clothes always matter. And now you’re googling “best yard-work outfits” or something ridiculous.

So, what is a man to do if he doesn’t want to obsess about clothing? Do we really always have to be "on"?

This was my question when I started diving deeper into clothing philosophy, sociology, anthropology, and even theology. I wanted to find a better framework for how men should interact with their clothes. As I studied and talked to older men in the industry, I feel like I began to develop a more nuanced framework on how to think about clothing. Which now brings me to the third approach, I call the “Clothing Decrescendo.”

C) “The Clothing Decrescendo”:

Clothes have a massive impact on our first interactions with strangers, but a much smaller effect on those who love us most.

My relationship with my wife is a great example. To this day, she remembers what I was wearing when we first met. In first attracting her, what I wore communicated who I was (when she had no other context), so it was super important. Even on the first couple of dates, how I dressed was important to attract and communicate that this relationship was special. If I wore old, janky sweats in those first interactions she might have still liked me... but, maybe not. My clothes might have actually obscured her ability to get to know me better.

And with time, my clothes became way less influential. Once we were at the “I love you” stage, it was okay to dress down around each other. After getting married and having 4 children, I doubt that she’d leave me for wearing ratty sweatpants. The relational impact of clothing is almost nothing at this point. And if you take the wedding vows seriously, "in good times and in bad," applies to your appearance, as well.

This applies to every other type of relationship, too (friendships, employees, clients, etc.). The further you get to know someone, the less downside your clothes represent. As people get to know the real you, your clothes become a nice garnish, but not the substance. And this is freeing. 

A quick "watch-out" though: Does this mean we should always dress sloppy around our loved ones? I say, absolutely not. It just kicks the conversation about clothing out of being a liability ("will this person reject me?") into an asset ("how can I show this person that I value them &/or delight them aesthetically?"). In the latter world, I think that is actually where the BEST fashion choices get made—when you are dressing from expression rather than from fear of rejection. 

I believe this is a better way to think about clothes.

Under my framework, the problem with A) “Clothes Always Matter” is that you’re essentially saying “people will never accept me for more than my appearance." Or, in other words, “I dress like no one loves me.” Which is crazy because that literally is what destroys Don Draper in Mad Men—he never lets people in. By always being “on” you can effectively push away those who love you most.

But B) “Clothes Never Matter” is naive, right? It states, “everyone loves me and appreciates my personality”, even when they have no context or relationship. And that's just not true. 

As I started to lean into this mindset, I found a lot of freedom in how I dress. Last week, when I went to a baseball game with my dad and son, I dressed comfortably and had a great time—because those people love me. And if I’m going out with my closest friends, I can experiment and wear something weird or different, just for the fun of it, because I know they won’t reject me (goofy or not).

So, when I start to worry about what I’m going to wear, I ask myself, “How well do these people know me?” This frees me up to be sober about clothing’s impact without ruining baseball games or parties. I hope that helps. It's made a big difference for me.