A Proper Suit
Whether you wear it weekly or once a year, a classically tailored suit is crucial.
There's always going to be one that you reach for most. Make it good and keep it clean.
Tailored chinos and quality jeans are just as good with brogues as they are with sneakers.
Sneakers, dress shoes, sandals... No closet is complete without (at least) one of each.
Don't treat accessories as an afterthought. End your look on a good note.