At the bottom of the Start screen for OOTP, there is a clickable word "Settings". hit that. A pop-up will appear with a bunch of, well, settings... go to the far right tab on the pop-up (Troubleshooting) and select "Open Folder Containing Customizable Data". There are folders called ballcaps, jerseys, and pants. Place each item in its respective folder.
I don't think the naming conventions let them load automatically. But in the Team Home page you can go to the Team Settings and look for the Modify Team Logos, Colors, etc. and then go to the tabs for each uniform item and assign it from there. When you try to manually assign a jersey for example, it will open up that folder you put the jersey in - just remember what it was named to navigate to it. Good luck
