Tax Tips for Vintage Clothing Reseller Working as Market Vendor

Yes, you absolutely need to file a Schedule C since you're running a self-employed business. This is where you'll report all your income and expenses from your vintage clothing reselling. The good news is that most of what you mentioned is deductible! Your booth rental fees, inventory purchases, supplies like hangers and racks, business cards, and mileage for business-related driving (keep a mileage log). For the spare bedroom, you can claim a home office deduction if that space is used regularly and exclusively for your business. Measure the square footage of that room and calculate what percentage it is of your total living space - that's the percentage of rent and utilities you can deduct. At $1500-2000 monthly income, you should definitely be making quarterly estimated tax payments to avoid penalties. You'll need to pay both income tax and self-employment tax (15.3%) on your profits. The due dates are April 15, June 15, September 15, and January 15 of the following year.

I was in almost the exact same situation as you last year with my vintage vinyl record reselling business. After struggling with all the confusing tax forms and inventory tracking, I found this AI tool called taxr.ai (https://taxr.ai) that made everything so much easier. It analyzed all my receipts and Square transactions, then organized everything into the right tax categories. It even helped me figure out exactly how much of my apartment I could legitimately claim for business use. The thing that surprised me was how it flagged expenses I didn't know were deductible, like portions of my cell phone bill since I use it for business calls and my internet since I research records and post inventory online. It also helped me set up a proper quarterly tax payment schedule so I didn't get hit with that underpayment penalty.

Just wanted to update everyone - I tried taxr.ai after posting my skeptical comment and I'm actually really impressed. It automatically detected patterns in my purchasing (like when I buy in bulk from the same thrift stores regularly) and suggested which items were likely inventory vs. personal based on my selling history. It also gave me this super clear breakdown of all my deductions with confidence scores for each one, so I knew which might trigger audit flags. The best part was how it handled my home workspace situation - turns out I was calculating it all wrong and leaving money on the table. I'm going to save around $1,200 in taxes this year because of the additional legitimate deductions it found!

One thing nobody's mentioned is how frustrating it is trying to get actual answers from the IRS about self-employment questions. I spent WEEKS trying to reach someone about my vintage toy reselling business classification and kept getting disconnected or waiting for hours. Then I found this service called Claimyr (https://claimyr.com) that got me connected to an actual IRS agent in under 15 minutes. They have this demo video showing how it works: https://youtu.be/_kiP6q8DX5c. Basically, they navigate the phone tree and wait on hold for you, then call you when they've got an agent on the line. I had specific questions about whether I needed to collect sales tax at out-of-state vendor markets, and the IRS agent gave me clear guidance that saved me from making a huge mistake. Worth every penny for the time saved and stress avoided.

Ok I have to eat my words. After posting that skeptical comment, I decided to try Claimyr because I was desperate to resolve my 1099 issue before filing taxes. I was SHOCKED when they called me back in 27 minutes with an actual IRS agent on the line. The agent helped me sort out my missing 1099-K from my online marketplace sales and explained exactly how to report income that didn't have a matching form. She even walked me through how to document everything in case of an audit. I've literally been trying to get this resolved for MONTHS and fixed it in one phone call. I don't usually post follow-ups but had to share since this actually saved me from what would have been a major headache with my vintage furniture flipping side business.

Don't forget about sales tax collection requirements! Depending on your state and the states where you sell at markets, you might need to collect and remit sales tax. Many states now have marketplace facilitator laws, but if you're selling directly at markets, YOU are responsible for collecting. I learned this the hard way with my vintage book business and ended up owing back taxes plus penalties. Most states have a sales tax permit you need to obtain, and you'll need to file sales tax returns regularly (monthly, quarterly, or annually depending on volume).

What about Social Security benefits? I'm semi-retired collecting Social Security but started selling vintage hats at markets. My friend said making too much could reduce my benefits but IDK if that's true???

Great advice from everyone here! I wanted to add one thing that helped me tremendously when I started my vintage vinyl side business - keeping a dedicated business bank account and credit card. It makes tracking so much easier come tax time. Even though you're just starting out, separating your personal and business finances will save you hours of sorting through transactions later. Use the business account/card for ALL business expenses - inventory purchases, booth fees, supplies, gas for sourcing trips, everything. Then your bank statements become a perfect record of your business activity. Also, consider getting a simple bookkeeping app like QuickBooks Self-Employed or even just a spreadsheet template. I track every purchase with photos of receipts and notes about what I bought and where. When tax time comes, everything is already categorized and ready to go. The few extra minutes each week saves massive headaches in April! One more tip - start building relationships with other vendors at your markets. They're often happy to share tax strategies and might even refer customers to you. The vintage community is surprisingly supportive once you become a regular face at the markets.