First time the dress up menu shows just leave him in... that little number and assure him that kind of exposure is back in style.
As for Storm. Well I'm not sure if it matters which new clothes you get but the jacket lets you take the home visits line which counts for "nice things for Storm". There's also checking out the children section at the library, hanging out around the city center, hanging at the diner, and some other things.
for hinterlands: donate clothes; visit Storm's house; visit P's house; have dinner on the archeological site; hang out with storm in town plaza; read the fiction section at library; and talk to storm at the pond. the order doesn't matter much just pay attention that the seventh day you have limited options, i know the pond is available in the last day.
