Chapter Two: April Influences Mr. April
Mr. A is a widower and he had often found himself wearing things his first wife bought that he didn't particularly care for, e.g. Cosby sweaters.
Shortly after her death, he went to a company holiday party and a stylish friend mocked his pleated khakis. He immediately laid in a supply of all-season charcoal wool dress pants to replace the Connecticut khakis. (His job was in Manhattan, where they expect a bit more.)
He's a uniform dresser: a tight palette of black, grays, and whites and a formula for most occasions. It works for him and I like it for him too. Now that he works from home he's far more casual. He also began working out in earnest and all the gray dress trousers were donated - too big.
My goals for myself in his wardrobe journey were and are
1. not to inflict anything on him that he hates
2. to help him determine what he actually does like
3. to steer him gently from truly dreadful choices if he's going out. At home, I mind my own business.
Once he figured out what he did like wearing, I helped him learn where those things could be acquired, often accompanied him there, and introduced him to concepts such as "all trousers need not have pleats and cuffs" and "a belt with jeans is 100% optional" and "other shoes exist besides black dress shoes, boat shoes, and sport sneakers."
Lately, as I've mentioned elsewhere, Little Mr. A has been buying him wardrobe gifts and making recommendations. He's a cool dresser himself and has known Mr. A for many years so he knows what to recommend and when the comfort zone is best left alone. Mr. A trusts him implicitly on matters of what looks cool and trusts himself on whether it's comfortable.