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Chief
Go for the tube top with leather pants, and don’t forget the sunglasses and glitter if you feel bold.
Chief
Unless it’s cold don’t wear a cardigan in summer
Chief
Wear an undershirt to protect you from sweat stains. Like a secret cardigan
If it’s a nice restaurant, a grey/navy suit with a polo/dress shirt, but maybe switch it with a pair of dark jeans if the setting’s more casual
Chief
Crisply pressed formal trousers, starched tux shirt, waistcoat with pocket watch, cummerbund, ascot, monocle, tophats, and a finely engraved walking stick to complete the ensemble
Rising Star
Like a true early 20th century business magnate
Bring a sport coat. Easy enough to take off if it’s hot / you’re over dressed