I noticed that when I use AwesomeMod, outerwear that the game generates for all sims in town is weird. It remains the same as everyday wear sometimes it adds gloves. It works fine without AwesomeMod.
I have been using AM since long before Seasons came out, so when I saw that, I just figured it was another EAxis fuck-up, to go along with all the other fuck-ups they left behind. Given that most of the outfits from everyday also show up under outerwear, I am not surprised they wear the same shit. I just ignored it.
At first I tought the same, but then I got curious and decided to start fresh game without AM and it worked ok.