Will It Fly Tax-Wise? It Depends.

A relative recently asked me, "Can I deduct the cost of the clothes I have to wear in my business?" I know the two words people hate to hear from attorneys are, "it depends." In tax analysis this expression is not a copout; it's a statement of how tax law works.  It's not always clear where the line of demarcation is between "it might work" and "it will work."