Literally, tailor-made clothes are clothes a tailor made for one particular person, measuring that person's body, so the fit is exactly right — not bought ready-made off a shop rail. From that, the word grew a much more common meaning: perfect for one particular person or purpose, as if it had been made for them and nobody else. "This job is tailor-made for you." "The course is tailor-made for beginners." Usually it is a compliment, and it carries a small feeling of luck or good fit — the thing and the person match without any pushing. You will hear it about jobs, courses, roles in a film, a house, a holiday. Sometimes companies use it about their service to mean "we will change it to suit you": a tailor-made travel plan, a tailor-made insurance policy — here it is close to "custom" or "personalised", and it is a selling word. Occasionally people use it about something bad in a joking way ("a situation tailor-made for disaster"), meaning it could not have been better designed to go wrong. British English says tailor-made most; American English often prefers "custom-made" or "made-to-order" for real clothes, but keeps tailor-made for the figurative meaning.