Why I Started Wearing the Same Outfit Every Day

Small decisions distract from the important ones. How simplifying your wardrobe can change your life.

learn more about Dylan Ogline

By Dylan Ogline

Opinions expressed by Entrepreneur contributors are their own.

I was terrified that people would notice. I waited with baited breath for someone to call me out on it. At a cocktail party … at a charity volunteer event … hell, even on a Zoom call with my team. And I'm their boss!

Walking on eggshells, I counted down the days until someone said it: "Hey, isn't that the same thing you wore yesterday? And the day before that?" But no one has said anything yet. Probably because they are too concerned with their own lives to care about what I was wearing, as long as it covers the things that are supposed to be covered in polite society.

My gambit had worked. I had successfully edited my wardrobe to the point where I essentially wore the same thing every day. The same brand and size shirt, the same pants, the same shoes … and my business was better for it.

You might wonder how making my wardrobe slightly less interesting than a bowl of plain white rice has anything to do with the success of my business.

Related: What's the Difference Between Business Casual and Smart Casual? A Handy Guide on How to Dress. (Infographic)

Think about this, though: Can you remember a time when you saw Steve Jobs wearing anything other than a black turtleneck and baggy jeans? Or Mark Zuckerberg wearing anything other than a T-shirt in Facebook-colored heather blue? (Other than when he wears a suit to testify in front of Congress.)

These guys could afford a decent wardrobe, right? Or at least some variation? But the truth is, the decision of successful people to get repetitive with their wardrobe is critical to doing what they do.

Related: Why Eating the Same Thing for Breakfast Every Day Helps You Make Better Decisions

Decision fatigue

In 2016, a study was published under the intriguing title, "Is There an Ideal Time of Day for Decision-Making?" Spoiler alert: Yes, there is. Argentine scientists studied 100 habitual players of strategy games to see whether they made better decisions in their game-playing in the morning, afternoon, or evening.

The study stated, "We found that players changed their decision-making policy throughout the day: Players decide faster and less accurately as the day progresses, reaching a plateau early in the afternoon."

In other words, our decision-making is slower and more accurate in the morning, but as the day progresses we become impatient and make snap-decisions — decisions more likely to be wrong.

Your decision-making power is finite. A kind of fatigue sets in the more decisions you have to make throughout the day. So why in the world would you expend this priceless, finite resource on something as trivial as what to wear? What shirt goes with which pair of pants, what shoes match with them.... How many of you go through this ritual? Standing at your closet, staring, deciding what to wear as you suit up for work, gird yourself for battle?

This goes hand-in-hand with why I recommend meal prep for everyone, or meal-delivery or a personal chef if you can afford it. At its lowest level — meal prep — you pick your day that's lightest on decisions. For most of us, that's Sunday. You prepare all your food for the week that day and store it in Tupperware to grab-and-go. Voila, you've just eliminated three whole decisions from your day, decisions you could use to develop your business and income strategy.

This is also why you set up a morning routine. You don't want to waste your precious decision-making power deciding which shaving cream to use or which room to meditate in. Standardize it, so you don't have to think.

Your wardrobe? Same deal. Choose a small collection of simple, high-quality garments, buy multiples of the same thing, and make sure they all go well with each other so you can never go wrong. I even have one color of shirt I prefer for meetings, one for Zoom calls and one for social events, and I know which shoes I like best with each color shirt. I'm really dialed in.

Related: Decision Fatigue Is Destroying Your Focus, Motivation and Drive

Suiting up

I was afraid someone would comment on the repetitiveness of my wardrobe. No one did, but paring my wardrobe down to a minimal selection had an unexpected side effect. Someone noticed when I didn't wear the same damn thing every day. I was going to a social event and I decided to change it up and wear a printed long-sleeve button-down instead of my go to shirt. Not in black as well. I know, crazy! Someone I had seen at several events commented, "You look different, Dylan. Did you change your hair?" I hadn't changed my hair. Just my wardrobe. And that's when I realized that, without realizing it, I had given myself a uniform. Like an In-N-Out employee, or Captain America.

Like Jobs and Zuckerberg, I had established a trademark look and people now expected it of me — even found comfort in it. It represented my brand. I think my acquaintance was even thrown off by the fact that the button-down covered my tattoos, which were always on display when I roll up my sleeves.

There's power in a uniform. It anchors your physicality with the intangibles of your brand, like your commitment to customer service and your expectations of your clients and your team.

Related: 9 Ways to Combat Decision Fatigue

Other techniques to avoid decision fatigue

Your wardrobe isn't the only place where you can reduce decision fatigue. After all, this is all about avoiding fatigue and focusing your decision making on things that matter. Here are some more ways to maximize your precious early-morning reservoir of strategic thinking:

  • Plan your day the night before. If you use your first precious hour of work time deciding what you're going to do that day, you're already starting at a deficit. Instead, plan your early-morning tasks the night before. If something pressing comes up, you can always change it on the fly. But have a plan the night before, so you don't waste your early morning mojo.
  • Do the toughest or most important tasks first. In addition to making the rest of your day feel like a cakewalk by comparison, frontloading the hardest tasks will give those tasks the benefit of your peak decision-making prowess for the day.
  • Delegate, outsource, automate. Entrepreneurs wear many hats by necessity, but the more responsibility you take on for your own business, the more decisions you have to make. Try to only have one task that you and only you can do.

Related: What Is Business Casual? Here Are 9 Classic Looks for Men.

If possible, your job as the business owner is to set the course and focus on growth. Delegate, automate, or outsource everything else. Even if it means spending more money than you are comfortable with, it will be worth it if you can focus on growth and execution. Workers move faster when they only have one task in front of them. So get stuff off your plate as soon as possible, so you can focus on the one thing that matters most: making that cash register ring.

Dylan Ogline

Founder of Ogline Digital

Dylan Ogline is an entrepreneur, investor and author. He is known as a pervader of work and lifestyle optimizations. He is founder of digital marketing agency Ogline Digital. A student of Stoicism, he enjoys playing hockey, reading and traveling the world.

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