Authenticity Isn’t What You Wear. It’s Why You Wear It.
A menswear reflection on intention, presentation, and the hidden dress codes we all follow.
I was listening to a financial-planning podcast recently when a viewer asked a simple question:
“Would you hire a financial advisor who doesn’t wear a suit?”
The two hosts—both casual dressers—jumped in eagerly. Their answer?
A resounding no, they’d never wear a suit. Suits, to them, were fake. Dishonest. A costume. Even a red flag.
One host compared suit-wearers to caricatures of old-school financial excess.
The other said he’d feel like a “poser” if he put one on.
Both insisted that the “authentic self” should always reign.
And then—without a hint of irony—they added a caveat:
If you’re young, don’t dress like a slob.
Their conversation was funny, sincere, and revealing.
And to be fair to them, this mindset has become incredibly common in the post-corporate-dress-code world.
I Used to Think Exactly Like Them
Before going any further, I need to admit something:
I used to hold the exact same view.
Fifteen years ago, suits felt corporate, stiff, and performative. Tailoring felt like selling out. Dressing up felt like pretending to be someone else.
I didn’t want to be the guy in the blazer.
I didn’t want to look like I worked “for the man.”
I didn’t want clothing to become a costume.
So I understand exactly where these podcasters are coming from. Their skepticism isn’t malicious—it’s rooted in an honest desire not to be fake.
But here’s what I eventually learned:
You don’t escape dress codes by dressing casually. You simply adopt a different one.
The Great Dress Code Swap
Over the last 10–20 years, corporate America dropped formal dress codes. Suits faded. Ties disappeared. “Business casual” melted into “tech casual.”
And a new uniform emerged:
The familiar combination of chinos and a polo
A quarter-zip fleece when it gets chilly
Shoes that aren’t sneakers, but aren’t quite anything else either
We didn’t eliminate expectations.
We just traded one set for another.
This wasn’t freedom—it was a cultural shift.
And one that came with its own signals.
The New Respectable: Casual as a Moral Badge
What struck me during the podcast wasn’t their preference for casual clothing—it was the moral weight they attached to it.
To them:
Suits are fake.
Tailoring is performative.
Dressing up is suspicious.
Effort signals deceit.
Casual equals honesty.
Hoodies equal authenticity.
That isn’t neutrality.
That’s a new hierarchy.
Anti-suit snobbery disguised as anti-snob values.
They reject being judged for wearing a hoodie—yet openly judge anyone who wears a suit. Their comparisons to “fancy” financial stereotypes revealed a deeper assumption:
Casualness has become culturally coded as more “real.”
Formality has become culturally coded as inherently fake.
That narrative isn’t truth.
It’s just the cultural current of the moment.
My Shift: What I Eventually Learned
As I grew older, worked with clients, and stepped deeper into the world of tailoring through SPO 33, something in me started to shift.
And here’s the causal glue that connects it all:
What changed wasn’t my personality—it was my understanding of what clothing actually communicates.
I learned that:
A well-cut jacket isn’t a lie.
A suit doesn’t hide you—it frames you.
Fit communicates care.
Intention communicates authenticity.
Dressing well is not selling out.
Tailoring can be profoundly human.
The problem wasn’t the suit.
The problem was the story I was telling myself about it.
Clothes Always Signal Something
This is where the podcast hosts were unintentionally honest.
They said clothes “shouldn’t matter,”
but then said young advisors shouldn’t dress like slobs.
They said suits are deceptive,
but insisted that their casual wear signaled honesty.
In other words:
They know clothing signals something—they just prefer the signals they’re sending.
Let’s just say it plainly:
A suit signals something.
A hoodie signals something.
A polo signals something.
Even “I don’t care what I wear” signals something.
There is no such thing as neutral clothing.
Which is why the heart of this whole conversation is simple:
Authenticity isn’t what you wear. It’s why you wear it.
Where I Agree With the Podcasters
One point they made is absolutely right.
They said young advisors need to “earn” the freedom to dress casually.
And they’re correct—not because suits trick anyone, but because clothing communicates readiness:
Respect
Credibility
Maturity
Focus
Awareness of context
Not performative.
Not deceptive.
Just adult.
When you’re in your early 20s asking someone twice your age to trust you with their money, their strategy, or their security, presentation matters.
That’s not conformity.
That’s stewardship.
Dress With Intention, Not Ideology
Where I part ways with the podcasters is their belief that casual equals authentic and formal equals fake.
I’ve simply lived too much life to believe that anymore.
Here’s the truth as I see it now:
You can be authentic in a hoodie.
You can be authentic in a suit.
You can be fake in a hoodie.
You can be fake in a suit.
Clothing doesn’t determine honesty or deception.
But intention does.
And tailoring—done well, with the right fit—can be a deeply personal expression of who you are and how you choose to show up in the world.
So my encouragement is simple:
Dress with intention, not ideology.
Choose clothing that tells the truth about who you are.
Not who a trend tells you to be.
Not who a subculture tells you to be.
Not who a podcast warns you not to become.
And if a well-fitting suit helps you feel grounded, confident, or present?
That’s real.
That’s you.
And that’s authentic too.
The goal isn’t perfection.
It’s presence.
If you're going to play the sport, you have to wear the uniform. I use that as a rule of thumb. I follow my client's lead on how to dress.