Costume ideas for main character

For our main character we need to show his personality through what he wears in order to communicate to the audience. So our main character is a young man of our age right now (so that's around the 16-17yrs of age) This is around the time when people get there first jobs and go for interviews. Of course this is a big moment in all of our lives and we want to demonstrate this event honestly with a little bit of comedy involved as well, similar to Simon Pegg's work.
So we are going to need to combine the organised smart business man that this boy is likely to become and the reckless clumsy stereotype that he his today.
We would therefore need a smart suit to represent the characters organised smart side but with a few noticeable imperfections like a partly untucked shirt or a dodgy tie.

Smart suit

Baggy badly done up tie 

 

We would be looking for something inbetween these two examples as we want to show that he has tried to do well with his appearance but he still needs to learn how to do some things.