The Real Way to Dress for Success

The way you dress sends signals to the real world; here’s how to make sure you’re sending the right ones.

On its own, “dress for success” is kind of an absurd piece of advice. (Though you might find the specifics detailed by Rishi Chullani in How to Dress for a Networking Event and How to Dress and Prepare for an Interview less vague and actually useful.)

Think about it. Who gets dressed, thinking actively about being successful for the day, and decides to look like a slob?

Sure, you might be dressed awfully — but that’s not the point. You believe you’re dressed for success, and if no one is there to tell you otherwise, how would you know you’re not?

Bad advice. Let’s dig in there and make it actually helpful.

When you’re at an event that would make “dress for success” appropriate:

There is more than the clothes you don to consider. That is your uniform. And a uniform is a vital piece to your attire, but there is more.

There is also your style and your confidence. Together, these three will actually help you “dress for success.”

Uniform for Success

You should definitely get clothes that make you look good. Obvious, right?

What’s not obvious is that you should have someone pick them out for you. A stylist, your girlfriend / wife, or some stylish friends who can be brutally honest about what looks good on you and what doesn’t.

(Eventually, you’ll be able to do this part yourself.)

Find out what looks good and get a bunch of it. That’s your uniform.

The Real Way to Dress for Success

Style for Success

Your style is a bit more than your clothes. It is the overarching “theme” of your clothes.

I’m not a stylist or fashion expert, so I can’t say what is or isn’t considered a “style” — but I know it’s more than your clothes.

Take someone like Mark Zuckerberg: jeans, a grey t-shirt, and maybe a black hoodie. That’s his uniform. His style is something like minimalist, relaxed executive.

The Real Way to Dress for Success

Confidence for Success

This is the ultimate part of your wardrobe that you need to put on every day.


Confidence in your look. Confidence in your abilities. Confidence in yourself.

If you don’t think it makes a difference, you are so wrong. Go look at any executive. Any successful executive… I’ll bet they are ultra-confident.

Now look at them. What’s their uniform look like? Their style?

Let’s put them all together in the real world.

I hate neck ties. They’re nothing more than a pretty noose in my eyes. Hard to tie, easy to look bad, get in the way…just a nonsense accessory.

Personally, I’m a bow tie guy. That’s just my style.

The Real Way to Dress for Success

It ties as easy as shoe laces, looks pretty sweet, and it puts you in the company of Bill Nye and Dhani Jones.

So when I’m at an event, like a wedding, I bow tie it up.

And every single time, without fail, a someone talks to me about it.

Sometimes it’s a woman (sorry ladies, I’m married) trying to strike up a conversation. Sometimes it’s another confident guy looking to talk to someone that doesn’t suck.

My uniform — nice looking shirt + pants + jacket — gets people to notice me. My style, the bow tie and overall relaxed look of it all, gets them to approach me or be open to talk when I approach them. My confidence gets them to respect me and actually converse with me instead of just waiting for their turn to talk.

If you’re going for that job interview, meeting to raise money for your company, video interviewing freelancers to build your app, or asking that girl you like out on a date, you need to really dress for success. Not just your clothes, not just your style, not just with confidence, but all three.

The total package.

That’s how you should be dressing for success.

Steve Eakin of Startup Black BeltThis guest post was written for The Art of Charm by Steve Eakin. Steve is a startup founder, Jeet Kune Do black belt, and taco addict. He is the CEO of Startup Black Belt: Helping people build, grow, and scale their startups and the CTO of VenPath: Helping apps create a new revenue stream from their data.

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in Art of Business, Art of Personal Development, Art of Style, Empowerment, How to Dress, Networking, Self Mastery