In my closet right now, I have 6 different color alligator shoes (Brioni, Tom Ford, Zilli) all well over $2k each, I have a couple Artioli Ostrich shoes ~$1,500 each. I spent stupid money on clothes. I use to have a tailor and would spend thousands on suits and shirts. I spent $24k on clothes in one sitting one time. A buddy of mine spent over $32k the same day. That tailor is one of the most well known in Los Angeles today and he basically started his business on us. $300 shirts, $500 Pancaldi ties, $500 cuff links, shit was crazy. I can't even wear most of the shit today.
To the Ops original post, I lost $20k in less than 2 hours at the blackjack table at Crystal Palace in the Bahamas many years ago. I was signing so many markers I didn't even know how much I had lost (I've never taken out a marker since). This was my first day of a 8 day trip. I was fukkin pissed. I had an early tee time that I passed up at the tables. That was the most expensive tee time I ever missed. I stayed on the beach the next few days drinking/binging as I avoided the casino. Later in the week I said fukk it and took $500, rolled it all the way up and won my $20k back and another $10k. Well, of course, my dumb ass, I gave the $10k back before I left. I was banging my head in disgust on the plane not believing I gave that money back. I use to fly down there 2/3 times a month and use to go on tilt at least 30% of the time.