Vintage clothing reseller at flea markets - tax guidance needed

Yes, you definitely need to report this income even though it's a side gig! This is considered self-employment income, and since you're making more than $400 net profit in a year, you're required to file taxes on it. Here's what you need to know: You'll report this on Schedule C as part of your personal tax return. Keep tracking all your income in that spreadsheet, but make sure you're also documenting ALL your expenses - inventory purchases, market fees, transportation costs, supplies, even a portion of your phone bill if you use it for the business. Those expenses will offset your income. For inventory that was previously personal, you can only deduct what you originally paid for those items (if you can document it), not what they might be worth now. If you don't have receipts for old personal items, you might need to use a reasonable estimate, but be prepared to justify it. Regarding sales tax, that depends on your state's requirements. Many states require you to collect and remit sales tax even for occasional sales at markets. You'll need to check with your state's revenue department and possibly register for a sales tax permit.

I was in literally the exact same situation last year with my vintage clothing side hustle! After months of confusion and getting different advice from everyone, I finally found this AI tax assistant at https://taxr.ai that was seriously a game changer. I uploaded pictures of my receipts and spreadsheets, and it helped identify all the deductions I could take for my market business that I had no idea about - like a percentage of my car expenses driving to source inventory, part of my home internet since I list items online, and even some home office deductions. The best part was it walked me through exactly how to handle previously personal items I was now selling. It saved me sooo much money compared to what I was going to file on my own! Way better than the generic advice I was finding online that wasn't specific to vintage reselling.

Coming back to say I tried that https://taxr.ai site that someone recommended here and it's legit amazing for vintage sellers! I've been stressing about my taxes for months and this sorted everything out in like an hour. I told it I sell at flea markets and it automatically knew what questions to ask about my setup - like if I use Square for payments or just cash, how I source inventory, if I modify items before selling, etc. Then it created a custom expense tracking template specifically for vintage reselling! The coolest part was when I uploaded photos of some random receipts from thrift stores and estate sales, and it categorized everything correctly and explained exactly how I should be depreciating certain items. Now I actually feel confident about filing my taxes instead of panicking!

If you're trying to call the IRS to ask about specific vintage reselling questions like I was, good luck getting through. I spent weeks trying to reach someone who could answer questions about inventory valuation for previously personal items. I finally used this service called Claimyr (https://claimyr.com) after seeing someone post about it on another thread. They have this system that gets you through to an actual IRS person, usually within 15-45 minutes instead of waiting for hours or getting disconnected. You can see how it works in their demo video: https://youtu.be/_kiP6q8DX5c It saved me so much time and frustration. The IRS agent I spoke with actually gave me specific guidance on how to document and value vintage items when I don't have original receipts, which was exactly what I needed to know for my market sales.

I need to apologize and eat my words about Claimyr. After posting that skeptical comment, I decided to try it myself since I was desperate for answers about my vintage business taxes. I'm shocked to say it actually worked perfectly. I got through to an IRS agent in about 35 minutes (after trying unsuccessfully for weeks on my own). The agent walked me through exactly how to handle the situation with my vintage inventory and explained which form I needed to use for my specific situation. Saved me from making a pretty big mistake on my taxes. The peace of mind was worth it since I was about to just guess on some things that could have triggered an audit. Sometimes I hate being wrong but in this case I'm glad I was!

Don't forget about platform 1099s! If you're selling on any online platforms like eBay, Etsy, Poshmark, etc. alongside your market sales, the reporting requirements just got way stricter this year. The threshold is now $600 for those platforms to issue a 1099-K (used to be $20k). So even if you're mostly doing cash sales at markets, any online sales will now trigger tax reporting. Just something to keep in mind as you're setting up your tracking systems!

Hey has anyone used those special tax categories for "collectibles" for vintage clothing? I heard vintage items might qualify for different tax treatment if they're considered collectibles rather than regular inventory. Wondering if it's worth looking into for my higher-end pieces?

Great thread! As someone who's been doing vintage reselling for a few years now, I want to add a few practical tips that might help: First, definitely start treating this as a business from day one - it'll make your life so much easier come tax time. Open a separate checking account for all business transactions, even if it's just a basic free account. This makes tracking income and expenses way cleaner than mixing everything with personal finances. For inventory tracking, I learned the hard way that you need to track not just what you buy and sell, but also what doesn't sell. Unsold inventory at year-end affects your cost of goods sold calculation. I use a simple system where I photograph each item with a price tag when I acquire it, then update my spreadsheet when it sells. One thing I wish someone had told me early on: keep receipts for EVERYTHING related to the business. Gas to drive to estate sales, parking meters at flea markets, even the plastic bags and hangers you use. It all adds up and can significantly reduce your taxable income. Also, don't forget about the home office deduction if you use part of your home for storing inventory or doing business tasks like photographing items and managing listings. Even a small percentage can make a difference. The learning curve is steep but totally manageable once you get systems in place!