[greymule]

If you're an official, you're a private vendor in business for yourself. You will probably file a Schedule C (profit or loss from business). If anyone reports the money he paid you, it will be on a 1099 form. That jacket is most certainly 100% deductible. You bought it to promote, market, or advertise yourself and your services. That stuff about wearing it on the street applies to employees who receive W-2 forms, not private vendors supplying services. (That would be the Schedule A that Bob M mentions. In fact, the deductions you take as an official appear on Schedule C, not Schedule A.)

If half the phone calls you make involve officiating, then half your phone bill is deductible. If you use your cell phone 90% for officiating purposes, then 90% of your cell phone bill is deductible.

Most businesses lose money their first year. There's nothing unusual about having a loss, even a significant one, your first year officiating.

Just a note: the standard tax programs (e.g., Turbotax) are generally made for people who receive W-2 forms from their employers. A sports official would need the version that includes Schedule C. That version usually costs about double the standard version. (But it's well worth it, and anyway, you can deduct the entire cost of any tax software you purchase.)