Since episode 1 is all about raising all of Olivias stats to 5, the walkthrough is slightly limited to how much it can help at that time. In order to give her any of the outfits that you buy, you have to go to the living room after picking her up from school (the highlight button should appear above the living room after school if you have brought the outfit).
If you can upload your save file, I can take a look for you and see if anything has gone wrong.
Edit: While looking into the issue for you, I discovered a major issue which makes it impossible to progress if you buy the wrong outfit (even if you buy the correct outfit the second time), which I can only assume is the issue that you're experiencing. I have just updated both of the mod posts to fix this issue, so hopefully reinstalling both mods should solve it for you (you may or may not need to set Olivias 'love' stat back to 3 though).
If this doesn't solve the problem, feel free to let me know and I'll do what else I can to help.
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