Matching Outfits for dating outing?

yea, that's a good plan. If it's a tie situation, go either red blazer - black shirt - red tie, or black blazer - red shirt - black tie,

Get both colours in and don't have two adjacent items the same colour.

Wear a two button suit and have them both up or wear a three button with the top, middle, or top-and-middle done up. Don't do up the bottom button on a traditional three button, it'll pull the material a weird way.
 
Looks like a prom or something. I'd definately try to match. Black suit, red shirt, black tie.

Or if you know she won't mind, get a black suit with red pinstipes.

Or if you are totally crazy, you could do an all red suit or a white suit with red pinstripes.

I prefer one of the 1st two methods, but thats me. If you go with the black/red pinstripe then I'd wear a red shirt and black tie.

If you are getting a vest you can mix it up and wear a black shirt/red vest/red tie instead.
 
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