The Success Paradox: Why I Dress Like I’m Not Trying (Because I’m Not)

Success isn’t about looking the part — it’s about being the part. And sometimes, being the part means showing up in sneakers and a hoodie.

Success changes you — just not in the way you expect.

I used to think climbing the career ladder meant three-piece suits, polished shoes and ties so sharp they could cut glass. Turns out, it means hoodies, sneakers and maybe remembering to iron a shirt for a big meeting (maybe).

The more established I’ve become, the less I care about dressing to impress — because confidence is the real power suit. And honestly? It’s the most liberating lesson I’ve learned in my professional life.

The Corporate Dress Code Myth

You’ve heard it before: Dress for the job you want.

Early in my career, I took that to heart. I suited up, played the part and did my best to look like “the most promotable person in the room.” And sure, there’s something to be said for looking sharp — but eventually, I realized that competence speaks louder than collars.

Like the time I showed up to an important work meeting in a blazer so tight I couldn’t raise my arms. I looked the part … until I couldn’t reach across the table to shake someone’s hand.

Lesson learned: Dressing up means nothing if you can’t function like a normal human.

Success = Freedom to Be Yourself

It took years, but I finally cracked the code: Success isn’t about earning the right to wear nice clothes — it’s about earning the right not to care.

When you’re confident in your skills and secure in your role, there’s no need to rely on wardrobe tricks to “sell” yourself. You’ve already proven you belong. At that point, why not be comfortable while you do your best work?

I’ve never been more productive than in my favorite T-shirt, backwards (gasp!) hat or hoodie — the one that’s been through countless brainstorming sessions, meetings and at least two questionable coffee spills. Success isn’t measured by how you look — it’s measured by what you do.

The Psychology of Dressing Down

Fun fact: Studies show that people are actually more productive and creative when they’re comfortable. Makes sense, right? You’re not distracted by stiff collars, pinching shoes or the existential dread of wearing real pants.

There’s also something disarming about dressing down — people find you more approachable and real. When you show up in sneakers and confidence, you send a subtle message: I’m here to work, not put on a show.

Am I making a bold statement by dressing this way … or am I just lazy? Honestly, both. And I’m OK with that.

How to Dress Down Without Looking Like You’ve Given Up

Now, let’s be clear — dressing down doesn’t mean looking like you’ve completely surrendered to the chaos of life. There’s a sweet spot between “high-powered exec” and “person who just woke up in a tent.”

?Here’s the formula:

• Well-fitted jeans or chinos? ??
• A casual blazer over a T-shirt? ??
• Sneakers that say “cool” without screaming “skater kid from 2004” (Not going to lie, I actually wear skater shoes exclusively) ??

The goal is “cool-but-capable” — like you accidentally became a CEO and you’re still kinda chill about it.

Why This Mindset Matters

The bigger picture here is about more than clothes. It’s about rejecting outdated notions of what “success” is supposed to look like. It’s about embracing authenticity, owning your skills and letting your work speak louder than your wardrobe.

At the end of the day, people respect results — not how well you can tie a Windsor knot. So show up, do great work and let your output do the talking (even if your outfit whispers “I hate ironing”).

The Success Reset

Success doesn’t come from looking like you belong. It comes from proving you belong — and realizing you’ve got nothing left to prove.

So, if you see me in a hoodie or an Arsenal jersey at the next big meeting, just know I’m serious … about being comfortable.