Are clothing and haircuts deductible if I need to look professional for clients?

Almost never, and this is one of the most common audit triggers. The IRS allows a clothing deduction only if the items are required for work and not suitable for everyday wear, like branded uniforms, safety gear, or costumes. A nice suit, business-casual outfits, or grooming fail the test because you could wear them outside work, even if you never would. Haircuts, makeup, and gym memberships are treated as personal expenses regardless of your profession, with rare exceptions for performers with specific requirements. The logic is that anything with personal use is not an 'ordinary and necessary' business expense. Deduct the branded polo with your logo; leave the dry cleaning of your regular wardrobe off the return.