You Said The Party Needed Buffs (Patreon)

 Masaru wears women's clothing because it accentuates his muscles. Will wears women's clothing because it has all the best casting bonuses. A tailor had to let his old gear out a little bit, but he can still do the job!  Will is rolling in cash, because there's always high demand for a back row caster who can strangle or pummel any mobs that get past the front.