I started new because I make some wrong decision (around 10 hours playtime) and I have had no save anymore that I can fix it.
The dress problem I have had was I accepted the Quest (Opera Quest with Kira) before I have had the Quest to go with Jane in the clothing shop to see the saleswoman for dressing the dress for you (Second Dress for Opera for Kira). Only online buying was available so it was not acceptable.
I played it to the end my playtime is around 15:15 hours.
look_skywalker helped me a lot to solve the Game with the best possibilities.
With the summer dress I have had no problems (the most expensive one). The selfie was not the 3rd missing the first one was missing after I heard my mistake it was no problem. The other wrong choices I done was not curable anymore so I started new. I load a lot around to solve my mistakes so I don´t know what I have done before and what not in my save. In the new play I saved immediately after I get the selfie.
The 3rd selfie from Kira is no problem to get at 10am at weekends when you go out before with her to a picnic.
After the dress you buyed the food in the main hall around 12am and then you searched for the right picnic place (you put a blanket on the place). After this you tell Kira that you are ready for a picnic with her.