If your group is already flirty or comfortable with each other, consider just arranging a night of strip poker. Otherwise you may want to get your friends together and let the game happen organically.
If someone does feel too shy, however, you don’t necessarily have to kick them out if they are interested in staying to watch. They might change their minds after watching a few hands.
Consider deciding how far the game will go and when it will end. Some people might be happy to play until they are completely nude, but others might only feel comfortable stripping until they are in their underwear. Agree on the limits, as well as if and how players will stay in the game once they have run out of clothes to shed.
Play five-card draw. Probably the easiest version for a casual game of strip poker. Each player is dealt five cards and gets to exchange one or more of those cards for an equal number off the top of the deck. They bet or fold before and after the exchange and the remaining player with the highest hand wins. Play Texas Hold’em. Each player is dealt two face-down cards and looks to combine them with a pool of five gradually revealed community cards. There are several rounds of betting, and the remaining player who can make the best five-card hand wins.
You can combine your game of strip poker with truth-or-dare. Let players who lose all their clothes keep playing with different penalties if they lose, such as having to answer a truth or do a dare. Just keep your dares within a realm everyone is comfortable with.
Alternatively, have only the player with the lowest hand in each showdown strip. This is a slower version of the game, for a more extended evening of fun. If you want, you can let players fold early in the hand—such as before the flop in Texas Hold’em—to avoid having to strip. However this obviously gives shy players the option to hardly participate at all, which can defeat the fun of the game.
With this variation especially, make sure no one in your game is likely to get jealous or territorial. In a group of friends it can be fun to find out who wants who to show a little more skin, but not if the answer is going to make anyone upset. Don’t pick on any one person. Conspiring just to strip down one player completely, especially in a larger group, is less fun, and can feel uncomfortable and predatory to that person.
Different items of clothing can either all have the same value, or can increase in value the closer they put a player to being naked. For instance if socks are worth $10, a shirt might be worth $30, and an undergarment could be worth $60. If a player trades in some clothing and later wins a large pot, you should decide whether he or she is allowed to buy back some of their clothes. Letting them buy back some modesty adds a further layer of strategy to the game, while having players stay stripped keeps the game moving.