I'd say depict the superstrategists the way they do in the stories: vaugely Batman-ish heroes (dark, less eye-catching costumes; reliance on cunning and gadgets) that give out orders and are usually team leaders or the right hands of the team leader. Their costumes/personas don't seem to be based around intellect either. Darksider, Emerald Blaze, Skeleton Steele, and so on. Of course despite Steele's bit of narration about the costumes of strategists, Emerald Blaze's name would suggest that "non-eye-catching" is not a hard and fast rule.
The Union seems to go out of their way to give each super an individual and distinct costume and persona, make them into a character, but beneath that skin-deep layer they seem to be treated like interchangeable parts; several codified tactical roles. Of course there are exceptions, like the solo missions that show up in the stories a little.
The fact that they're a bunch of highly trained professionals in body armor working together as a team should help the costumes work. And when you have a single hero in the spotlight, narratively depicted as more comicbooky, sheer characterization should pull off the feat.
Also, what will overall make the costumes work is how important they are to the story. Inside the Pyramids Union members have to wear domino masks at all times, even when they're alone in their rooms. How creepy is that?
