This seems like a tricky one, but surprisingly isn't. Depending on the line of work, there are easy ways to "dress up" or "down." Let's take the Wall Street corporate for example, he would typically just need to loosen up his tie (or remove it), discard his suit jacket, possibly replace it with a blazer and undo the first few buttons of his shirt.
It's as easy as that. A quick spritz of cologne and a last ruffling of hair, and the Wall Street corporate has now evolved into Mr Charming.
Whether you are heading for a casual lunch or a low key-dinner, the Sunday brunch look works for both. What is this Sunday brunch look you ask? Pairing a simple pair of chinos, a tucked-in polo or a classic button down shirt with some Mantorii-esque shoes, is the Sunday Brunch look!
It's important to remember that it might be better to stick to the lighter colours in this scenario, rather than the blacks, to give more of a laid back vibe.
Now for the, I'm really trying to impress her, dates. It really depends on the level of swanky here, but if you have two tickets to the Opera, a perfect fitted suit may be a great option. Try to steer clear of the average black suit as you may again be confused with the Wall Street corporate.
A more colorful yet classic suit is perfect for such an event. We have some great options here with the Navy Glenpaid or possibly the Ari Gold? One last tip: if you feel that a suit is absolutely necessary for the intended date than go right ahead, but most first dates don't call for such formality.
These guidelines are not set in stone so feel free to play around with them. Hopefully, you will have a great first date by following some of these tips. If not, at least you'll be dressed for it.