High-rolling is a phrase used to describe someone who is affluent, has a lot of cash, or is living a luxurious lifestyle. Synonyms for high-rolling include terms such as rich, wealthy, prosperous, and affluent. Other synonyms for high-rolling are loaded, flush, comfortable, and well-off. For those who are financially successful, esteemed terms like prosperous, opulent, and rich are suitable. Some people use the word baller or boss to describe themselves when they are living a high-rolling lifestyle. In conclusion, whether you prefer formal or informal language, there is no doubt that there are plenty of synonyms available to describe a high-rolling lifestyle.