You have self-admitted limitations in your wardrobe. why not just try and put your best suit/shirt/tie combo together when dressing? i understand what you want to do, it just doesn't seem you have the gear to pull it off well.
^^ No, it would not. The red tie with pink shirt isn't a terrible idea given the choices. The white shirt and plaid tie would be best given the choices of wearing with a dark blue shirt and lack of options.