In this country breakup tune, Hardy wears his boots to bed so it will be easier to walk out the door, and out of his girlfriend's life, in the morning. The song was based on a semi-true story of an angry partner and a pair of too-tight boots. The singer told Songfacts in a 2020 interview
"I was in New York City and I had just played as the headliner of my first sold-out show. My girlfriend Caleigh was with me and I was just a tad bit over-served. After the show, I picked her up over my shoulders and was walking down the street. There was this garbage can with a bag that had a bunch of Styrofoam in it, and I picked her up and I didn't throw her, but I laid her down on top of the bag. I was in the dog house big time, as I should have been, and she stayed pretty pissed at me for the rest of the night. Then we got back to the hotel room and I had these really tight, tough-to-get-off python boots, white boots, and she was so mad, so she didn't help me take my boots off.
The next morning we woke up late to catch the train to Washington, D.C. and I was still wearing the clothes I wore the night before. And I just wrote that idea down. I woke up in my boots, and I was like, 'How could you make that cool?' I thought, 'Oh, I know. What if you knew you were going to get kicked out the next day, so you woke up in your boots. It would give you one less thing to do when she's yelling at you in the morning.'"