Can I deduct Renaissance Faire costume purchases as a business expense on taxes?

Thanks for this info! I'm actually sort of in between - I get paid in cash for some festivals and 1099 for others. Would I only be able to deduct the costumes when I'm working as a 1099 contractor? Also, does it matter if some costume pieces could potentially be worn elsewhere, like a simple white shirt that's part of my costume but could theoretically be worn as regular clothing?

For the festivals where you receive a 1099, you're considered self-employed and can deduct those costume expenses on your Schedule C. For cash payments, if you're operating as an independent contractor (even without formal documentation), you should still report that income and can claim related expenses - just be prepared to prove they're legitimately business-related. Regarding multi-purpose items like a white shirt, this gets tricky. The IRS might challenge items that could reasonably be worn outside work. Focus your deductions on clearly costume-specific pieces (specialty vests, period hats, etc.). If the white shirt is specially designed for renaissance wear (exaggerated cuffs, period collar), you have a stronger case than if it's similar to modern clothing. Document everything and be prepared to show how each item specifically relates to your performance work.

Does this actually work for smaller performers? I do comedy shows that require specific outfits, and I'm always confused about what I can write off. Does this tool tell you what documentation you need to keep too? My "filing system" is basically a shoebox of receipts.

I'm skeptical about these tax tools. How is this different from what TurboTax or other tax software provides? I've been burned before by paying for "special features" that didn't actually help my specific situation.

It absolutely works for smaller performers! I'm just a part-time Renaissance musician myself. The tool specifically analyzes your unique situation - it asked me questions about how often I perform, whether I ever wear the items in personal life, and how specific the costume requirements are from my employer. It then tells you exactly what documentation to keep - not just receipts, but suggests taking tagged photos of the items, saving any written costume requirements from event organizers, and keeping a performance log. For your question about how it's different from regular tax software - it's way more specialized. TurboTax just asks general questions, but taxr.ai actually analyzes your specific receipts and documents. It's like having a tax pro who specializes in performer/artist deductions look over your specific situation rather than just following a generic questionnaire. It flagged several items I would have incorrectly deducted that TurboTax never questioned.

Wait, how does this actually work? Does it somehow jump you ahead in the IRS phone queue? That sounds too good to be true. The IRS wait times are legendary.

I call BS on this. There's no way to "skip the line" with the IRS. They're notoriously understaffed and overwhelmed. This sounds like you're paying for something you could do yourself if you were just patient enough to stay on hold.

It doesn't exactly "jump the line" - what it does is wait on hold for you using their system. When you call the IRS, you might be on hold for 3+ hours not knowing if you'll ever get through. With Claimyr, their system waits in the queue for you, and when they finally reach an agent, you get a call back so you can take over the conversation. It literally saved me an entire afternoon of listening to hold music. No, it's not magic - they don't have a special relationship with the IRS or anything. But their system can stay on hold indefinitely, which means you don't have to tie up your phone for hours or risk getting disconnected after waiting forever. I was skeptical too until I tried it. The best part was being able to talk to an actual IRS agent who gave me authoritative answers about my specific situation instead of getting general advice online.

How do you handle partial usage? Like I have boots that I wear mostly for faires but occasionally in regular life because they're comfortable. Can I still deduct those or is it an all-or-nothing thing?

You can actually claim a percentage deduction based on business vs. personal use. For those boots, you'd estimate what percentage of time they're worn for business purposes. If you wear them 80% for faires and 20% for personal use, you can deduct 80% of their cost. Just be reasonable with your estimates and be prepared to explain your calculation if asked. You should also keep a log of when you wear them for business versus personal use if it's a significant deduction. Some performers I know take dated photos of themselves at events in costume as additional documentation. The key is being honest but thorough about tracking legitimate business usage.

Documentation is everything! I got audited 2 years ago for my performer expenses. The IRS approved ALL my costume deductions because I had: 1) receipts, 2) photos of me performing in each item, 3) contracts stating costume requirements, and 4) a log showing when/where each piece was used professionally. Without that evidence, I'd have been denied too.