I got both endings, thanks in part to the tips given below (though it is interesting that Gail absolutely refuses to wear anything joyful herself, such as the semi-hidden sailor suit).
This is quite well-written and atmospheric. The slow bitcrushed music and the faded, almost sepia-toned colour scheme create this sense of times long past, especially in conjunction with the oldschool (1900s) outfits. Gail having shorts and cropped hair is the biggest push away from this older feeling, and it's a sign of her own rebellion.
The writing is seriously good, too. Nothing is explicitly shown, but what's happening is still pretty evident during the finale scenes. I also *really* like that the characters chat about the clothing options as you're picking them; I'd love to see that in more narrative dress-up games, as it really gives the clothes more history and gravitas.