The Wisdom of a Three-Year-Old
Leo is three. He loves dinosaurs, trucks, and making his own decisions about what he wears.
Last month he refused to wear a perfectly nice button-down shirt for family pictures. He wanted his dinosaur t-shirt. We compromised on the dinosaur shirt under a sweater. He was happy. The pictures turned out great.
That moment made me think.
After decades of helping men choose clothes for important occasions, a three-year-old reminded me of something simple I sometimes overcomplicate: how clothes make you feel matters more than how they look to everyone else.
What Leo Cares About
Leo’s priorities when getting dressed are crystal clear:
Comfort — Nothing itchy. Nothing too tight. Nothing that restricts his ability to run, jump, or climb.
Fun — Dinosaurs, trucks, bright colors. He wants to wear what makes him happy.
Control — He wants to pick. Even if the choice is between two blue shirts, he needs to be the one who decides.
Sound familiar?
Most grown men want the same things. We just use bigger words and more complicated reasons to describe it.
The Adult Version of Dinosaur Shirts
Think about it. When you put on a shirt that fits well, feels good against your skin, and makes you feel confident, you move differently. You stand taller. You’re more present.
When you wear something that pinches or gaps or makes you self-conscious, you spend the whole day adjusting, tugging, and feeling slightly off.
Leo won’t tolerate that for a second. He’ll rip off anything that doesn’t feel right. Maybe we should take notes.
Lessons I’ve Relearned from My Grandson
Lesson 1: Comfort is not giving up.
Leo doesn’t wear uncomfortable clothes just because they look nice. He refuses. Grown men often suffer through bad fits because they think they’re supposed to. Don’t.
Lesson 2: Confidence comes from within the clothes.
When Leo wears his favorite dinosaur shirt, he lights up. He roars. He feels powerful. The right clothes for you should make you feel like you — only better.
Lesson 3: Sometimes compromise is smart.
We got the dinosaur shirt and the nice sweater for pictures. Leo felt in control. The family got the photo we wanted. Everyone won.
In adult terms: you can wear the reliable navy sport coat but pair it with a shirt that actually makes you happy.
Lesson 4: Trends don’t matter to happy people.
Leo doesn’t care what’s in style. He cares what feels good and looks fun to him. Most of us would be happier if we followed that more often.
The Boardroom vs. The Playground
A man in a boardroom wearing a suit that doesn’t fit will feel just as restricted as Leo in an itchy sweater.
A man who feels good in his clothes — whether it’s a perfectly broken-in polo or a well-fitted dress shirt — carries himself with the same natural confidence Leo has in his dinosaur pajamas.
The difference is that adults have learned to ignore discomfort. Leo hasn’t. Maybe he’s smarter than us.
What This Means for How I Advise Customers
When a man tells me he hates shopping or hates wearing dress clothes, I think of Leo now.
I ask different questions:
How does this feel when you move?
Would you want to wear this for a few hours?
Does it make you feel like yourself?
If the answer is no, we keep looking. Life’s too short to wear clothes that make you miserable.
Diane and Leo’s Influence
My wife Diane loves when Leo gets dressed himself. She says it’s good for his independence. I’ve started applying the same thinking on the sales floor.
Sometimes the customer knows what feels right better than I do. My job is to help them find the version that also looks appropriate.
To Every Man Reading This
You don’t have to wear dinosaur shirts to work (please don’t). But you should pay attention to how your clothes make you feel.
Find the versions of adult clothes that give you that same Leo confidence — the ones that fit right, feel good, and let you focus on living instead of constantly adjusting your collar.
Stop wearing things that make you feel restricted, embarrassed, or uncomfortable. Life has enough real problems. Your clothes shouldn’t be one of them.
My New Rule
Before I leave the house each day, I ask myself the Leo question: “Would three-year-old me be happy wearing this?”
If the answer is yes, I’m probably doing something right.
Thanks, Leo. You’re teaching your old granddad more than you know.
Now if you’ll excuse me, I need to go find my bowling shirt. It’s Thursday night, and I hear there’s a dinosaur shirt with my name on it for next weekend’s family pictures.
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