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Leather chafes. I have a good quality shoulder holster, and it takes about 30 seconds of wearing it without an undershirt to teach one the error of doing so. Add in the weight of a pistol, and it really digs. You'll acclimate to wearing two shirts. I did. I wear two shirts even with a belt holster.

Best shirt I've found for accessing a shoulder holster is a pearl-snap shirt. Yeah, people will ask you where your horse is. But unless you're fond of replacing buttons, a snap-down is the only way to go. T-shirts and polos don't really give you that good an access; they bunch up and drag on the gun, holster, and hand.