If I'm dressing up for a night out, it's usually a black shirt (unless white is required), black suit, black shoes, a tie if the occasion calls for it (probably with at least some black in it) and a grey fedora such as the one in my profile photo - very wide brim.
If I'm dressing down, it's jeans and whatever else strikes my fancy and suits the day's or evening's events (if any). T-shirts or dress shirts, sometimes a black tux shirt. Black shoe-like sneakers. A baseball cap, probably something to do with magic or playing cards - though on warm nights I might leave it behind. It's rare that I'm not either carrying a haversack or wearing a vest or jacket with lots of pocket space.
I always have at least two decks with me, one of which is usually a stripper. Wallets, keys, pens, pad, "indestructible" EATCT, titanium pocket knife (events permitting). I travel lighter when I'm dressing up, but I still have those decks.
Around the house - bathrobe, not much else.
My wife wouldn't have it any other way!
I'm naked... everywhere...
Not in your profile photo...
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