So each of the "small blue shirts" the client is buying goes to or relates to a different applicant?
If this is the case, it would seem reasonable to inject the applicant name or whatever identifier into the attribute structure. That would automatically make it work to display a product for each applicant.
I don't know how the client is supposed to indicate the applicant involved with each item... if they type in a name, that can be a standard text input attribute, which you can work on after processing to put the name in an "applicant" table in the db. (It will be in an "orders" table already.)
If they are supposed to select an applicant from an already populated db, there could be some sort of processing to put that into the option values and product attributes... can't say more on this as only you know how the base is set up.
What sort of scale is involved here? Dozens/hundreds/thousands of clients? Dozens/hundreds/thousands of applicants?



