Dress FOr Success

The case for: dressing for success

By Brett Kaufman

Dress for success or dress for your personality?

Everyday, we sit down for in-person meetings and there is always that fear: “Did I overdress? Or Worse, did I underdress for this occasion?”.

When you travel for days at a time, it can be tough to prepare for every circumstance. Do you need shorts, slacks, jeans or something else? Icons like Zuckerberg and Jobs kept it simple, we all knew what they’d be wearing, but what’s the common business executive to do?

Dressing for Success: when is business causal the right answer?

Do you try and tailor to the audience or do you always wear the same thing and set your own tone? Over my career I’ve been known as the sweater guy; you can usually can find me rocking one in NYC during my frequent visits.

Most important to me is to be comfortable and to reflect who I am. I’m a jeans and polo/button up – MAYBE with a jacket – type of guy, nothing more. Wouldn’t it be nice if we could all show up in shorts and just sit by the pool to get deals done?

What makes you feel the most comfortable when you sit down for a big meeting? Would you rather be dressed for you or for the room?

  • Vince says:

    Throughout my career I’ve noticed that the packaging can be more important than the product, especially with first impressions. I dress for the room for non-regular meetings, but I’ll dress more comfortable for people who are already familiar with me and my work.

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