The brief was simple. One evening in Monte Carlo, starting with a drink on the terrace of the Hôtel de Paris at eight and ending, if things go well, at a blackjack table in a private room at two. Five pieces, bought with that evening in mind, that will not look foolish the next morning at breakfast or the next winter in New York.

Look from The New Formal editorial
From The New Formal, Milan
  1. The midnight-navy dinner jacket. Not black. Black goes green under casino lighting; midnight navy goes black, which is the whole trick and has been since the Duke of Windsor. Unlined if you can find it, grosgrain lapels, and no vents. Berluti, Zegna and a good Neapolitan tailor all do it; the tailor does it best.
  2. The white evening shirt with a turndown collar. Wing collars are for people who read about dress codes rather than live in them. Mother-of-pearl buttons, no studs, French cuffs with the plainest cufflinks you own.
  3. A watch you can read in the dark. A table runs on time you do not notice passing. A simple dress watch, 36 to 38 millimetres, on a black leather strap, with a dial that does not reflect the chandelier. One watch. The man with the bracelet, the signet ring and the watch is the man the dealer remembers for the wrong reasons.
  4. Velvet slippers or patent oxfords, and nothing in between. The slippers if you are staying in the hotel and the casino is across the square. The oxfords if you will walk. Either way, shoes you can stand in for an hour at a roulette wheel without thinking about them.
  5. A money clip and a card case. Leave the wallet upstairs. A clip with the evening's budget, decided before the shirt went on, and a slim case for the room key and one card. When the clip is empty, the evening is over, and you walk back across the square looking exactly as good as you did on the way in. That is the only rule of the night that cannot be bought.

Everything above works in Baden-Baden, Venice and Macau. In Las Vegas, swap the dinner jacket for the navy suit and keep the rest. The budget in the money clip is the one piece of advice here that matters more than the clothes.