Yes, you should always keep your WordPress plugins up to date. You risk security vulnerabilities by exposing your website to out-dated software.
Make a backup of your website before making any updates. You will want to have the ability to restore your website in case the updates fail and break your site. Be sure to obtain a backup of the plugin files, and your database.
Check to make sure your plugin updates are compatible with each other and your current WordPress version. Keeping you website software up to date is a priority, but you will want to verify that the newest versions of your software can interact correctly with each other.
Once you have your backup files and ensure your software is compatible, begin updating the plugins from the Updates Page. Check the plugin tools to make sure everything is functioning as intended. If you keep your website maintained and up to date, then applying new plugin updates is a quick and easy process.