While I think it’s good to periodically update your look and image, in business it’s equally important to understand the markets you want to work with. For instance, if you went to a doctor because you are sick, I doubt if you would feel too confident if he came into the examination room wearing flip-flops, a messy lab coat and dirt under his fingernails. There is an expectation of what a doctor should present himself as, correct?
So this young fellow (about 40 years old) had a “normal” professional presentation for his industry. Owns a website development and social media services company as well as provides training. His usual dress was a crisp clean shirt, a pair of khakis, leather shoes, a clean-cut but full head of hair and dark glasses. He evolved into a coach more for business and life and adapted his look to be more edgy by shaving most of his hair, wearing the same glasses, a black dress shirt with white tie, jeans, leather shoes and a black fedora and an ear-piercing. A look more popular in the IT industry, and amongst gangsters. But he asked me, "Is it a power look?"
Hum…I said depends on who his target market is.
As an after thought, black shirts in general should only be worn with black ties or with an open collar. Keep the gangster vibe for your next dress-up party or wedding.