Dress for Success, Entrepreneurial Fashion 101

By: David Turner
Co-Founder of Waitbot

Being a well dressed entrepreneur is probably the most important thing you can do for you career besides having talent, a desirable product, a quality team, and access to capital and connections. Sadly most entrepreneurial classes, books, and articles overlook this vital success factor. This blog post provides a few simple rules that can transform any regular Joe, Amish, or Yao into a well dressed entrepreneur.

Rule 1: Don’t wear a suit. Suits are for investors and interviewees, not for the well dressed entrepreneur. Unsubstantiated research tells us suits crush the creative spirit and are high in cholesterol. Unless of course you’re wearing sandals, then you’re ok. Tuxedoes surprisingly have the opposite effect on creativity, and are highly correlated with brilliance and general awesomeness. However, only when used sparingly and you tie your own bow tie. In the age of YouTube there is no longer an excuse for clip-ons.

{If done right, a bow tie can compliment the startup tee, as seen here with WeDeliver whose tagline is “We Deliver In Style”.}

Rule 2: Choose your t-shirts with care. A t-shirt says a lot about who you are; your values, your personality, what promotional event you recently attended. A unique t-shirt with a clever techie or pop culture reference can earn you mad street cred, but only if your audience understands the reference so consider whom you’ll be working with before deciding on a shirt. Additionally big brand t-shirts are tacky and slap in the face to everything entrepreneurial, so save those American Eagle T’s for lazy weekends (though you should also considering throwing them away).

Rule 3: Keep it simple. Accessories are a fantastic medium for self expression and are often the centerpiece of a stylish and hip outfit, but be careful not to overdo things. Matching your kicks to your hat is stylish, but matching your fedora to your custom Smartphone case is annoying. The well dressed entrepreneur knows drawing too much attention to his or herself can have negative consequences. No one likes a peacocker.

In addition to following these simple rules of thumb, I’d also suggest bathing regularly and washing your clothes preferably with some type of detergent. While there are some notable exceptions (e.g. early Steve Jobs), clean bodies and fresh clothes make better products. As the late future Dave Turner once said, “Dress for the product you want, not the product you have”.