The answers to your questions follow:
1) - No. This is a personal expense and even though you did talk about your business there is not deductible tax expense.
2) - No. Everyday street wear is never deductible. If you have a name of your company as part of the clothing then you can deduct advertising. If you need specific safety clothing such as steel toed boots as example, those could be deductible.
3) - No. This is also a medical personal expense regardless if business is conducted. You can take the cost of the catalogs.
4) - No. TCJA has suspended all other entertainment expense deductions in 2018 through 2025. Prior to that, businesses were allowed to deduct 50% of the face value of entertainment tickets and events, and 100% of the cost to qualified charitable events, if the purpose was business-related.
This article will provide some information about these deductions. What types of meals and entertainment expenses are deductible on a business return?
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