The Psychology of Dressing Well (And Why You Must To Get Anywhere In Life)

I used to be a sloppy dresser. I never liked that I had to dress a certain way to get the respect I thought I deserved or to get people to listen to me.

“What a sham!” I would tell myself. “People should respect me because I know what I’m talking about, not because I’m wearing expensive socks.”

But then I experienced something that changed my mind completely.

Years ago, I was on the bus headed to a friend’s house. I knew the neighborhood but wasn’t sure which stop to get off at.

The gentleman sitting next to me noticed me looking out the window every few seconds trying to get my bearings and asked if I needed help. I told him my predicament, and he confidently told me I should exit in two stops.

I thanked him for the advice.

A moment later, another man standing in the aisle who’d heard my conversation leaned in and said, “Actually, you should get off at the next stop.”

I thanked him, hopped up, and exited just like he told me to, ignoring the advice of the first guy.

What was the difference between the two men? And why did I choose to listen to one and not the other? I asked myself the same question as I walked the last few blocks to my friend’s place. Read on for the answer.

Look Sharp, Be Sharp: How The Clothes You Wear Change What People Hear You Say

As I walked away from the bus, I realized in an instant why I listened to one guy and not the other.

The man in the aisle was dressed sharply. He looked like he was on his way home from work in a fancy office downtown. My seatmate was wearing sweatpants, had a dark stain on his t-shirt, and looked like he might have skipped showering that day.

In this moment, I realized just how many preconceived notions and stereotypes were built into my own assumptions of other people. Here I was complaining how people judged me by my clothes while I did the same to them—can I trust the instructions of someone who can’t be trusted to even keep food off his clothes?

I didn’t mean to make this judgment. It was simply years of social conditioning taking over. My decision process went into autopilot. If you want people to listen to you, there’s an important lesson here:

Dress the message.

The clothes you wear and the way you groom yourself will change the way other people hear what you say. It will subconsciously tell them if you’re like them or if you’re different. It will determine whether they listen or ignore. Trust or distrust.

I learned the same lesson again while climbing a mountain in Russia during an anti-terror operation.

The mountain was closed to all but locals and the mountain rescue team. We got in okay, but on the way out, there was a police checkpoint. Our driver was part of the mountain rescue team, but we weren’t. What do we do? We’re going to get in trouble!

“Fear not,” our driver informed us. “Just put these in your lap, and don’t say a word.” He handed us each a blue jumpsuit with the mountain rescue emblem on it as he changed into his own.

The policeman at the checkpoint stopped us and looked directly into my never-looked-more-American-in-my-life face. Then, he glanced at the blue jumpsuit in the seat next to me and immediately waved us through.

Nothing about me said “mountain rescue” except the jumpsuit. Turns out, it was all I needed.

This is the same reason every pharmaceutical company puts actors—and we  know they are actors—in white lab coats to pitch their drugs in their television commercials. We immediately judge them as doctors.

It’s why some mothers choose color-coded clothing for their babies. It’s hard to tell what sex a newborn is. But if you see one rolling around in a blue onesie, you know it’s a boy. Pink for girls.

How you dress yourself changes who you are. It changes the value of what you have to say. At least to the people who are looking and listening.

Dressing Well: Three Tips For Budget Shoppers

Whether you want to get a better job, get out of a traffic ticket, or start a worldwide movement, the way you dress and present yourself will play a major role.

You may not like this reality, but remember: those who succeed are not those who complain about “the way it is” or “the way it should be.” They’re the ones who accept reality for what it is, and use that reality to their advantage.

But what if you’re working with limited resources or, like me, want to play the game well but maintain your status as world’s most frugal shopper?

Here are a few tricks to dressing well on a budget, no matter what your aim.

Consider the audience and the message.

Think carefully about who it is you’re trying to influence and why. What do they care about and why is it important?

When you know this, you can present yourself in a way that focuses on those ideals.

The way you’d dress at a business conference full of middle-aged folks is different from how you would dress at high school sports game.

Think about who you’re talking to and what would make them trust you. The most expensive route is not always the most effective one.

Find a decent tailor.

Clothes that fit you incredibly well are expensive. But clothes that fit you pretty well and can by fixed with some simple tailoring can be quite cheap.

Look for bargains and closeouts on high quality clothes that don’t fit perfectly, but can be altered a bit. And tailoring need not be expensive, either. A dry cleaner can often take in sleeves and hems—simple alterations—for just a few dollars.

Dress in darker colors.

You can get away with buying cheaper clothes in darker colors because quality of fabric and construction don’t show through as easily the darker the fabric is.

This also comes with an extra benefit for people like me who always spill food on themselves. Darker clothes hide stains. You don’t have to abandon them after the first soy sauce incident.

Perhaps if Mr. Sweatpants from earlier had heeded this advice, I’d have listened to him!

Whatever message you’re trying to send to the world, never forget the clothes you put that message in will determine the way it’s received. So, dress it carefully.