A “High Roller” is someone who spends lots of money carelessly, blowing money fast and recklessly. The term originated from high stakes players who place large bets at the casino.
A schoolgirl who shortens a uniform skirt above the knee (or higher) by rolling the waistband. Typically done for comfort or fashion purposes. Rarely to be provocative.
High rollers are in the frontline of society's war on young women's bodies.
One of a group of 4 individuals that are highly skilled in poker and hustlepeople at the poker table. They always dress nicely at the poker table and have good table etiquette. A high roller is often feared by other poker opponents.
Bob: "I heard the high rollers were playing in this tournament."
Jake: "Yeah, they are the people with ties and triple everyone elses' chipstack."
Bob: "It's ok, we can always play for 5th place."