1. To remain functional or adequate despite long or continuous use. I bought this old car nearly 20 years ago, and it is still wearing well to this day.
2. To remain particularly popular or well regarded for a long time. Truly great poetry will always wear well, whether it was written this morning or 400 years ago. And yet, 30 years later, the unique aesthetic of the film still wears well.
3. To look very fashionable or attractive while wearing something, such as a piece of clothing, a particular hairstyle, a kind of makeup, etc. In this usage, a noun or pronoun is typically used between "wear" and "well." Not every woman can wear short hair well, but you really pull it off. I must say, for someone who tends to go against conventional styles, he wears a suit and tie very well.
4. To be particularly well suited to a certain demeanor, attitude, title, role, etc. In this usage, a noun or pronoun is typically used between "wear" and "well." The young king wears the responsibility and decorum of his crown admirably well. The former Olympian was recently made an ambassador to the United Nations, a role she wears well.
Last under continual or hard use; also, withstand criticism or the test of time. For example, These boots have worn well, or His poetry wears well. [Mid-1500s]