The Proper Blog

Are you an aspiring “entrepreneur, investor, executive, or technologist making waves in the New York digital business community” with no idea what to wear to the next networking event?

Suppose you’re an “entrepreneur” headed to the next New York Tech Meetup.  As you get dressed, you’re torn.  You’re supposed to be a young, independent, creative entrepreneur.  You want to  channel Kevin Rose with his baseball cap or Marc Zuckerberg with his fleece and sandals.  On the other hand, you think: “This is New York!  Gordon Gecko! Appearances matter!” – and you start reaching for the suit and tie.

If you had been a banker you wouldn’t have this problem… (no – you’d have much bigger problems)  but don’t panic – Proper Cloth has answers.

Thanks to a statistical analysis of the the glamor shots of the winners of the 2008 Silicon Alley 100, we can tell you definitively what outfits work on the New York technology/entrepreneur/investor scene, and which ones don’t.

Tie vs. No Tie

It seems that the SAI100 favor the cool and casual look of no-tie 62% vs. 38%.  When you consider that people might actually dress up for their glamor shots, this probably becomes even more distinguished.

Jacket vs. No Jacket

This one partially depends on the weather, but putting a nice suit jacket or blazer over your shirt definitely takes you up a notch on the casual-formal barometer.  62% chose to wear a jacket with their outfit while 38% wore a shirt by itself.

Outfit Summary

Putting it all together, we’ve broken down your choices into six options (only considering the top part of your outfit): A dress shirt by itself, a dress shirt with a jacket, a dress shirt with a jacket and a tie, a t-shirt, a tuxedo, and finally a polo shirt. As you can see, 35% of SAI100 winners sported the formal dress shirt, jacket and tie combo.  Second most popular was the dress shirt and jacket (sans tie) with 27%, and third most popular was the simple button down dress shirt top with 26%.

It’s important to note that those aren’t your only options.  Clearly you really can wear whatever you want as 8% rocked the Rose/Zuckerberg t-shirt look.

So, our biggest take away is that a good dress shirt can significantly increase your odds of becoming a successful technologist, entrepreneur or investor in New York (technologists: spare us the causality vs. correlation lesson).

Dress Shirt Collar Type For Entrepreneurs, Investors and Technologists

It’s one thing to dress well enough to fit in.  Now, it’s another to win the prize.  Over 80% of the SAI100 wear dress shirts.  How do you rise above the noise?  While most people think you actually have to be a big time venture capitalist or proven entrepreneur, Proper Cloth’s analysis proves that it’s actually how you dress that determines if you are in the top or bottom half of the SAI 100.  As you can see, while the top 50 favor the point collar dress shirts, the bottom 50 favor the spread collar dress shirts.

For the ambitous New York entrepreneurs, Proper Cloth has a straight point collar shirt worthy of the SAI100.  We also offer tailored dress shirts in various other styles – perfect for any occasion.  To learn more about the subtlties of dress shirt design, try designing your own dress shirt now.