👔 Your blazer doesn’t qualify. Your hard hat does.

Yes. And the absence of a 1099 does not mean the absence of a tax obligation. That’s the single biggest misunderstanding in crypto and it has cost people real money.

The IRS classifies cryptocurrency as property, not currency. That means every time you sell, trade, or exchange crypto — including swapping one coin for another — you’ve triggered a taxable event. Bought Ethereum at $1,200 and sold at $3,400? That’s a capital gain. Traded Bitcoin for Solana? Also a taxable event, even though no dollars were involved. Used crypto to buy a laptop? Taxable. The IRS does not care that you were just trying to buy a laptop.

What’s not taxable: buying crypto with dollars and holding it. Transferring between your own wallets. Receiving crypto as a gift (though your basis carries over from the giver).

What is taxable: selling, trading, earning crypto as income (mining, staking, airdrops), and using it to pay for goods or services. If you held the asset for more than a year, long-term capital gains rates apply — 0%, 15%, or 20% depending on income. Under a year, it’s taxed as ordinary income.

Starting in 2025, major exchanges like Coinbase and Kraken began issuing Form 1099-DA, so the “nobody sent me a form” defense has an expiration date. But even without a form, you’re required to report. The IRS added a yes-or-no digital asset question to the front page of Form 1040 starting in 2022, and checking “no” when the answer is “yes” is the kind of thing that ages poorly.

Track your cost basis. Use a tool like CoinTracker or Koinly if your transaction history is messy. Report everything.

Almost certainly not, and the reason is one of the IRS’s more philosophical distinctions.

Work clothing is only deductible if it is (a) required for your job and (b) not suitable for everyday wear. A nurse’s scrubs qualify. A construction worker’s steel-toed boots qualify. A welder’s protective gear qualifies. A suit does not. Neither do dress shoes, blouses, slacks, or anything else you could theoretically wear to a dinner party, a wedding, or a particularly formal grocery store visit.

The IRS doesn’t care that you would never wear your work clothes outside of work. It cares whether you could. The test is suitability, not actual use. A three-piece suit is suitable for everyday wear even if you personally would rather wear sweatpants, and the IRS is unmoved by your sartorial preferences.

Uniforms with logos or organization-specific features do qualify, as long as your employer requires them. If your company makes you wear a branded polo with the company name embroidered on it, that’s deductible (if you’re self-employed) or reimbursable (if your employer has an accountable plan). Military uniforms qualify if you’re prohibited from wearing them off duty.

For W-2 employees, the point is largely academic anyway. The Tax Cuts and Jobs Act suspended the miscellaneous itemized deduction for unreimbursed employee expenses through 2025, and the suspension was extended. Even if your clothes technically qualified, you can’t deduct them as an employee right now.

Self-employed individuals can still deduct qualifying work clothing and uniforms on Schedule C. The key word remains “qualifying.” Your blazer collection doesn’t count. Your hard hat does.

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No, and the options have gotten significantly better in the last few years.

A 529 plan was originally designed for college tuition and related expenses, and for a long time, using the money for anything else meant paying income tax on the earnings plus a 10% penalty. That’s still true for genuinely nonqualified withdrawals. But the definition of “qualified” has expanded enough that the money has more exits than most people realize.

K-12 tuition now qualifies, up to $10,000 per year per beneficiary. Private school, religious school, any accredited elementary or secondary institution. This was added by the Tax Cuts and Jobs Act in 2017.

Apprenticeship programs qualify. If your kid enters a registered apprenticeship, 529 funds can cover fees, books, supplies, and equipment. This was added by the SECURE Act in 2019.

Student loan repayment qualifies, up to a $10,000 lifetime limit per beneficiary. If your kid went to a trade school, community college, or a four-year program and has loans, you can use 529 money to pay them down.

The biggest change: Roth IRA rollovers. Starting in 2024, SECURE 2.0 allows you to roll up to $35,000 from a 529 into a Roth IRA for the beneficiary, subject to annual Roth contribution limits. The account must have been open for at least 15 years, and contributions from the last five years don’t qualify. But for families with older 529 accounts and kids who didn’t use all the funds, this is a genuine retirement head start.

You can also change the beneficiary. Transfer the 529 to a sibling, a cousin, yourself, or even a future grandchild. The money doesn’t expire, and the beneficiary can be changed as many times as you want without penalty.