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Being from the South, I cannot comment on attire either- but in the interests of being truthful, if blunt, the age issue is going to be the first hurdle to overcome.
There is much talk here about the southern houses and how "superficial" we are- but the fact is that applies at any campus with a strong Greek system. Any fraternity at any campus in high demand will have more candidates than it needs coming through as freshmen straight from high school- and so in that circumstance anyone who does not fit that standard life path is going to have a very hard time getting in.
The best advice I can offer is to have your friend visit the campuses where he might attend (or if he is still in service have someone visit for him) and just observe what Greeks are wearing. Look for letters and also look at who is coming and going from the top houses on those campuses.
Figuring out the right attire is not that difficult- but having to go to great effort to figure out the right attire at a competitive campus is in and of itself a bit of a warning sign because there will be little room for those not coming from a background where "they know" to succeed in rush.
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