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Howie Long and Michael Strahan look good in theirs. I look good in mine.
I'm a couple of years older than Howie, I'm guessing Strahan is older than you. Three piece's are definitely in style especially fall and winter.
T shirts are a good idea no matter what your size is.
OP does not say where he is, but JAB is having their buy 1 get 3 free through the end of the week.
Suspenders are a must.
Shop ebay looking for returns if needed. Thrift stores, etc. Tell those people at these stores to let you know...
The jacket is to short for my taste and looks like to much waist suppression from the back. The pants look to tight in the thighs from the rear, you can't even see the crease.
Did you gain 10-15lbs from the time you submitted your measurements?
Sounds like you need these Gobis while you can get them from the Shoebank.
Do you know your "friends" hat size?
Have you seen him wearing the style you have in mind, or do you "just think this one will look good on him"?
His taste and your taste may not be the same taste, he might prefer a fedora after all.