Don't know if i'm overthinking this

So on Wednesday I will have the money for the 350 pics plan. Now I need pictures for both Tinder and Instagram, because I'm in Milan and I want to approach everyday, and girls prefer IG over WhatsApp.

Before Tinder went to shit, I had success with a buzzcut: https://imgur.com/a/XGGFp4F

I have a high forehead and receding temples, which younger girls don't like. Only one of the girls I dated was 18. I figure it's better to hop on finasteride, minoxidil, and RU58841 to get my hair fuller and have the look that younger girls like more.
Barbers are competing with photographers on who's the lowest IQ, so I decided to cut my own to get some sort of fringe that will look better once all the meds start working.

https://imgur.com/a/ATmXuw1

I also like how I look with the right hat.

https://imgur.com/a/sxklk2b

So the fringe is a work in progress. The buzzcut pics are the old ones from Tinder and are just 3; I won't go back to buzzcut just to take pictures for AI; I have to finish the fringe experiment.

I can take hat pictures anytime; that would be the easiest. I also have multiple hats of that brand with different animals.

What type of pictures should I produce/give AI?

Also, any idea how should I approach girls, with a hat or with the work-in-progress, still-not-so-good fringe?

Thanks