Is a “Man Bag” (messenger bag) Recommended with a Suit?
Leaving out the part that wearing a bag make you look less manly, that’s another discussion, from style perspective only if you have decided you’ll wear a man bag (high-end leather messenger bag or leather accented camera bag – ipad sized) for a casual (non-formal) dinner should you wear a suit?
If the answer is yes, how about color matching, what color suits are recommended for a brown leather bag and what for a black leather bag? What color with get more miles?
Also if the answer is yes, how about a more formal gathering like a wedding?
If the answer is no, the only other solution is a briefcase, but briefcases are too big generally (most you can fit a 15″ or 17″ laptop), do you know one close to an ipad in size, or if that is impossible, for a 10-12″ size ultrabook/netbook?

I generally wouldn’t use anything other than a briefcase with a business suit. If you’re wearing a more casual social suit or a jacket and odd trousers, a leather one-strap bag is probably fine.
The bag should match your other leather — brown bag with brown shoes/belt, black bag with black shoes/belt.
Somewhere like a wedding I wouldn’t bring a bag of any kind. Your suit jacket should have enough pockets for everything you’re carrying, unless you’re the photographer or something.
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LikeDislikeA casual case rather than a business-formal case might also be a good option for you. It skips the messenger-style strap so that your jacket isn’t being flattened, but it looks more natural with a casual outfit. We did a video on business versus casual bags over at the Real Men Real Style YouTube channel that might help:
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