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Luckily I haven't run into this problem yet since being initiated (no duh from my signature...). I think it's the Pledge Master's responsibility to clearly outline what is appropriate attire in advance, also making sure to run it by the appropriate people first if necessary, and firmly relays this to the Pledge Class.
In short, I'm saying you should probably ask them to refrain from wearing strapless dresses at initiation.
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