Bespoke, period. Custom suits made by the guys on Saville Row is the pinnacle. H. Huntsmon and Sons, Gieves And Hawkes. Italian? Attolini. I'd have them use the finest worsted wool.
Shirts -- Alumo cotton, done by turnbull and asser or Lewin, on Saville. Maybe Kiton if I went Italian.
Throw in some 10k John Lobb bespoke oxfords and your good to go.
As mentioned, it's not about the brand...it's about the fabric, construction, fit and the way it wears. The tailors mentioned above are the best of the best, and they use the most expensive fabric.
I know people would look better than guys who wear $8,000 suits, and they shop at J Crew. There are a lot of wealthy guys with really nice clothing, who look like shit, because theit shit fits them incorrectly and they wear awful colors.