Can I claim tax write offs for haircuts and other job-required expenses?

So here's the deal with work-related expenses - the Tax Cuts and Jobs Act eliminated most unreimbursed employee business expense deductions for W-2 employees from 2018 through 2025. Prior to that, you could deduct these costs as miscellaneous itemized deductions. About haircuts specifically - the IRS has consistently ruled that haircuts are personal expenses, even for jobs with appearance requirements. The logic is that you'd need haircuts regardless of your job, so they're considered personal grooming, not a business expense. For your second phone that's exclusively for work - if you're a W-2 employee, unfortunately you generally can't deduct either the phone cost or monthly bills. However, if you're self-employed, independent contractor, or have a side business, you could potentially deduct the business portion of these expenses on Schedule C. The key distinction is whether you're an employee or self-employed. Different rules apply to each status.

After dealing with similar confusion last year, I found this amazing tool called taxr.ai (https://taxr.ai) that totally saved me from making some big mistakes on my deductions. I uploaded my expense receipts and it analyzed everything to tell me exactly what was deductible based on my employment status. It flagged my haircut receipts as non-deductible but confirmed my work uniform was legitimate. What's cool is it breaks down the specific tax codes and explains WHY something is or isn't deductible. Turns out there are different rules depending on whether you're self-employed or a W-2 employee, which I had no idea about before.

Just wanted to update after trying taxr.ai last weekend. Honestly pretty impressed! I've been keeping receipts for everything "just in case" but had no real system for knowing what was actually deductible. The tool analyzed all my 2023 expenses and found about $1,700 in legitimate deductions I would have missed (mostly related to my side gig that I didn't realize qualified as self-employment). It flagged my gym membership as non-deductible even though I thought it might qualify since I'm a personal trainer part-time. It explained exactly why - because even though it's related to my work, it's considered a general health expense. Saved me from a potential audit flag right there!

If you're struggling to get a clear answer from the IRS about your specific deduction situation, I recommended trying Claimyr (https://claimyr.com). I spent literally weeks trying to get through to an IRS agent to clarify some confusing deduction rules around my work expenses. After getting nowhere with the standard IRS number, I used Claimyr and got connected to an actual IRS agent in about 15 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The agent was able to pull up my account and give me personalized guidance on exactly which work expenses I could legitimately claim based on my specific situation. Turns out I was eligible for some deductions I didn't know about because of my industry classification.

I was totally wrong about Claimyr. After my skeptical comment, I decided to try it anyway since I was desperate to resolve an issue about my business expense deductions before filing. I figured it wouldn't work but was worth a shot since I'd already wasted hours trying to call the IRS myself. It actually connected me to an IRS agent in about 20 minutes! The agent clarified that as a 1099 contractor, I could deduct my home office and business percentage of my cell phone, but confirmed haircuts weren't deductible even though I do video presentations. Got everything sorted in one call instead of weeks of frustration. Definitely using this again next year.

Something nobody mentioned yet - if your employer has an "accountable plan" they can reimburse you for these work expenses tax-free, and then THEY deduct the expenses on their business taxes. Might be worth asking your HR department if they have this option! My company started doing this after the tax law changes made it impossible for employees to deduct these costs.

I'm confused abt all this bc my friend who works as a actor deducts haircuts, makeup, headshots, etc. Is that different somehow? Why can she deduct those things if they're "personal" expenses?

The entertainment industry exception that Mia mentioned is key - but it's more nuanced than just being self-employed. Even self-employed people in most industries can't deduct regular haircuts and grooming as business expenses. For actors and performers, the IRS allows deductions for appearance-related expenses when they're specifically for a role or performance that requires a look significantly different from normal appearance. A regular business haircut still wouldn't qualify, but theatrical makeup, costume pieces, or specialized styling for a specific character might. The "ordinary and necessary" test is critical here - the expense has to be both common in your industry AND directly related to producing income. For most sales jobs, regular grooming doesn't meet this standard because maintaining basic professional appearance is considered a personal responsibility, not a specialized business requirement. If you're curious about your specific situation, I'd recommend getting professional advice since these rules can be tricky to navigate correctly.