This is an awesome question :) Maybe I can offer some tips. - If you get leather shoes, I can recommend Cole Haan Zero Grand - http://bit.ly/2sQPdMe http://bi

This is an awesome question :) Maybe I can offer some tips. - If you get leather shoes, I can recommend Cole Haan Zero Grand - http://bit.ly/2sQPdMe http://bit.ly/2sQPdMe .. they are really comfortable. - For collared shirts, get the no iron ones and save yourself some trouble in the morning. - Stretch jeans can be a nice compromise between slacks and jeans and look something in between. - The last one may be seen as shallow.. but invest in a nice, timeless but not blingy dress watch (and a matching belt).. It pays over time and shows discernment - especially if its a corp job. You can buy vintage watches for pretty cheap. - Last tip.. (edit): go shopping with somebody else to challenge your own preferences and conventions.