Should the company buy the CEO, clothes?

Clothes can be business expenses. The IRS allows clothes deduction if they are used only for business purposes. Whether that's appropriate for the company depends on the board.

Yes, as long as you can justify it (like with the demo) it should be perfectly fine. In any doubt double check with your accountant.

No

If Not, you must not want that potential customer very much... Dress to impress- but only as much as the occassion calls for.......

Does the CEO make so little money, and have no money for clothes, that he/she can't afford it? If so, then yes, get him/her some presentable clothes! Who even cares if it's a deduction. However, if the CEO has enough money to catch a movie once-in-awhile, then he/she should be committed enough to pay for their own clothes.

ha ha...love this one!

for the company interest, yes...do get that.

well, you can - but it would have to be included as part of their taxable income. The IRS only allows deductions for work clothing that cannot be used in daily life (i.e. safety glasses, uniforms). Since he could wear that blazer somewhere else and it doesn't appear to be a work garment, it would be taxable.

Dressing down, ubiquitously known as “being comfortable”, says that you don’t care about how you look, as if your appearance were an entirely private matter that has nothing to do with anyone else. It’s the exact opposite: what you wear is part of the visible environment, as relevant as the architecture, the decor, the food on the table, the scents in the air. - Linda Grant