Wear Whatever The Hell You Want
Look down at your outfit.
Now look up and don’t ever put your head down again.
Here is the honest truth and maybe it shouldn’t be this way but it is: people are going to judge you by what you wear.
People that know you (friends and family) understand your personality and love you for all of your quirks but strangers have no choice but to judge you by your outfit because they only have that much information about you as they brush past you on the sidewalk.
Think about it: we have approximately 7 seconds to judge the threat level of a person who is about to approach us. In those 7 seconds, your brain has to figure out if the oncomer is likely to ask you for directions or for your wallet.
You have a few other key pieces of information available (such as their walking speed, belongings, and level of distractedness) but for the most part, your brain is judging your risk level based on their outfit.
So, the bad news is: your outfit needs to be a conscious choice.
The good news is: there are no wrong choices.