DPC never had parties that were final freeroam. They're usually either in the middle or last third of the episode. There were always major events after it.
Besides we don't know when the timeskip will happen. There will probably be two parties at all.
Josy sitting by the fire has a more conventional hairstyle.
Josy in the tent has the same hairstyle as in the episode banner.
We can assume that either
1) They are two different parties. Josie with the Padme-style hairstyle in the tent refers to the beginning of the episode
2) Josy with the ponytail hairstyle and Josy with the Padme hairstyle refer to the same time. Probably the outdoor party was either a camping trip, or they were outdoors for a few days which always made Josie able to change her hairstyle the next day.
Well. It's not about the past. How it was before and making an assumptions based on this and if it wasn't happened before then it will not happen now. And, technically, EP9 was exactly met this criteria. Someone expected at least something after the party but it ended together with the party.
If you making such assumption, then you probably expecting the episode to come further than Thanksgiving party and apropriate calendar day, which is unlikely. We are starting at the morning after the Halloween (last day of October - first day of November) while Thanksgiving day fluctuating usually in mid of 20 of November. It's more than 3 weeks. And we have a confirmation regarding back to classes and other events in college.
The most likely scenario is that we either spend a week in college (as it was in almost all previous episodes) and then time accelerates or there is a sharp jump to Thanksgiving. Or now the episodes will be made in such a way that we will play not by day basis, but through important scenes, classes and other events such as small parties with a time skip like a 2-3 days between them. In such case, it can do without a 1.5-2 week jump in time. But if you assume that everything will not end with Thanksgiving and a party in his honor, then you expect at least a few more days after this event. And if I'm not confusing anything - the DPC said that this party is the biggest free-roam event in the game and it happens at the end of the episode. I.e. this does not cancel any other free-roam events taking place before this party, as well as other parties.
There are no Josy in the tent. It's her & Heather room in the HOT's mansion.
1. It looks like a "date" or a romantic night with her, whatever. Let's stick to "spending time with girl". We seen Sage in restaurant, Riona in gaming room, etc. While same thing with Maya will probably take place in MCs room. On the "what branch will you play first?" banner there are clearly visible MCs gray couch on which Maya seats. And we also had a preview of Maya, when she came to MC with umbrella. Her hairstyle is the same and rainy autumn day is a perfect movies time (we know MC planned to invite her to watch some movies on his big TV).
2. If the camping and tents are all from the Thanksgiving party, then it should be considered as outdoor. Josy's new hairstyle is complicated and this is not something that is done in field outdoor conditions, in this case it is easy to assume why she is with her classic ponytail at this party.While Maya's new hairstyle just gives her a different look and doesn't look like a complicated styling.
There are only 2 confirmed previews and other renders from (probably) Thanksgiving party with girls in tents. With Maya and with Sage. No Josy, the only one preview with Josy on that party of her seating near MC while he plays on guitar.