Food and drink is not a deductible business expense, except that you can deduct 50% of the cost of food and lodging if you are traveling out of town for business purposes for at least an overnight stay.
Clothing is not a deductible business expense unless it is unique in some way that it cannot be worn for ordinary use. For example, a priest’s collar could be a deductible expense, but a black shirt and slacks would not be deductible.
Personal medical expenses are deductible on schedule A of your personal tax return, not on a business return. You could potentially set up an HRA, or health reimbursement arrangement, whereby your company reimburses you personally for medical expenses not covered by insurance. However, this requires legal advice, and would have to be set up for the future, it would not be retroactive to last year. It’s also more complicated if you are more than a 2% owner of the company.
If you have a dedicated business only cell phone or Wi-Fi connection, that is a deductible business expense. If you use your personal phone and Internet for work, there are two different arguments.
1. You can’t deduct any costs as a work expense if you are on a flat rate plan, because your work usage does not increase your cost.
2. You can deduct a percentage of your cost as a work expense if you have records that give you some kind of reasonable basis for how to divide the costs. You can’t just divide the cost in an arbitrary manner. You have to have some kind of record, or proof, that would give you a reasonable basis to calculate the percentage of work use.
I personally believe argument #1 is more correct, and I seem to remember reading a tax court case about it, but I don’t have the citation at hand. Some people will suggest that #2 is acceptable, it is on your own risk if you are audited.
