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Doesn't Turnbull & Asser do a three-button cuff?
The poster from Chicago (see #8) thinks so.
Sounds completely like MTM. Although Turnbull & Asser has 3-button barrel cuffs.
does T&A shirts have bright red translucent buttons?
I would not do this if I were you. It's just a bit awkward given your respective positions.
Just ask him. He'll probably be flattered because if he's wearing such a recognizable shirt then you can bet he wants to be recognized. And since the shirts seem custom or at least a particular brand then he obviously puts a lot of thought into them. People love to talk about things for which they have a passion. If he drove a rare collectible car you can bet he enjoys talking about it, the same goes for his fashion taste I bet as long as you don't mention price since that makes most people uncomfortable. "Is that a custom shirt? It looks great" is all you need.
I've bought shirts from Bernard Oyama that have all of the described traits -- three-button cuffs, contrast stitching, and interesting buttons. His stock changes all the time. Also, the shirts were made in Italy and may be sold under other labels.