Entrepreneur Style Guide: Fashion Tips for the Modern Entrepreneur

What compelled me to write this article about entrepreneur style is that I have gone to plenty of meetings where it can be hard to decipher what I should and should not wear. Just because you are a young entrepreneur doesn’t mean you should pull a Mark Zuckerberg and dress like your going to an 8 AM college class after a late night out. When you make billions you can do whatever you want, but for now, lets keep it classy. I meet with a lot of new clients, some range from CEO’s of multi-million dollar companies, to business owners my own age looking to get their start up off the ground. I typically break it down to into 3 scenarios. If are meeting with a high profile client, I would suggest going a bit more formal. For your younger clientele you can dress it down a bit, I suggest what I call Entrepreneur Casual, its a mix between business casual and casual, it’s just right!  When you have clients coming to your office, the ball is in your court. You can go casual to show that you have a laid back atmosphere which tend to appeal to the creatives, or you can go formal and show your client you run a tight ship. Be sure to let your client know before hand, you wouldn’t want to make them feel uncomfortable because that could end badly.

Below is a break down of some of my favorite entrepreneur style combos as well as some suggestions on what to wear to different meetings.

Entrepreneur Casual:

Shirt & Blazer: One or the other usually works well. If you are going blazer, I suggest a soft nice tee shirt or sweater with the sport coat or blazer over it. Make sure the blazer is fitted so that it doesn’t look too bulky when you are wearing it. If you are going button down, I suggest a pattern that pairs well with your outfit and maybe even a skinny tie or bow tie.

Mens Button Down
Entrepreneur Fashion


Pants: When it comes to pants, I go chino every time! It’s the staple crop to the entrepreneur style. They are comfortable, they typically have a slim and relaxed fit, and can be paired with any outfit. Chinos are relatively inexpensive depending on where you buy them.
Mens Chino Style

Shoes: When you are going Entrepreneur Casual I suggest a pair of Chukka’s, preferably suede. The prices can vary on the different brands typically anywhere between $75-$200 if not more.


Entrepreneur Formal: This is good for when you are meeting with those big corporate clients and you are going to their office for a meeting or presentation. You want to make sure you look sharp, but comfortable at the same time!

Slim Fit Suit:  Don’t borrow your dads out dated suit which will probably be to big on you anyway. There are plenty of deals out there to get a full suit for a pretty inexpensive price, think of it as an investment! I typically pair my suit with a skinny tie and a tie clip, both can be found in almost every mens department at any store.

Entrepreneur Fashion Tips

Shoes: When is comes down to it, it really depends on the suit you are wearing, if you are going navy, grey, or black suit I would suggest a black shoe, nothing too fancy. If you are wearing a a cream color suit or brown, I would pair it with some brown shoes, this also goes for chinos and a blue blazer, I would choose brown over black any day.



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