“Look, I come like a thief! Blessed is the one who stays awake and remains clothed, so as not to go naked and be shamefully exposed.”
Revelation 16:15
Even with all the Bible reveals to us about Jesus' second coming, people will still be caught off guard. Jesus says He will come like a thief, so He warns us to make sure that we are ready
How do you make sure you’re ready for Jesus’ return? Well, according to this verse, part of being ready is staying awake. Be careful not to allow yourself to be lulled to “sleep” by the enemy or by our world. You must keep your eyes open if you are going to see the signs that Scripture tells us will signal the end. If you want to avoid being caught off guard by Jesus' coming, the first thing you must do is stay “awake.”
The second thing Jesus mentions is keeping your clothes with you. “In the ancient Near East, conquering armies often paraded prisoners of war naked to expose them to as much shame as possible”* Can you imagine? Wanting to hide so badly but being completely exposed with no way to cover or hide anything from anyone. It would be awful!
So, being properly clothed in case of an attack was important. It could help you fend off your attackers. (It's difficult to fight for your life in your pajamas.) It could help you outrun them. (It’s hard to run for your life without shoes on.) At the very least being properly clothed when you were captured ensured that you weren’t embarrassed until and if they stripped you naked to parade you.
For believers “keeping our clothes with us” probably refers to making sure we are clothed with righteousness. Jesus is warning you to be careful not to sully yourself with the sins of the world. You don't want to end up ashamed when Jesus returns. Because when he returns we will all be exposed for what we really are. He will see what you have been doing, and there will be nowhere to hide.
So, are you ready? Are you staying awake? Are your eyes open to what's going on in the world? And are you keeping your clothes with you? Are you clothed with righteous deeds or will you be embarrassed when Jesus returns? Take Jesus' advice: "stay awake and remain clothed, so as not to go naked and be shamefully exposed.”
*John D. Barry, Douglas Mangum, Derek R. Brown, et al., Faithlife Study Bible (Bellingham, WA: Lexham Press, 2012, 2016), Re 16:15.