I prefer to wear a suit but invariably out dress my date.
Try not to do this. In general, women like men who dress in a similar style and at a similar level to themselves (attire says a lot about your views on many things, imo.) So, be yourself, but maybe a relaxed version of yourself. Dress to be comfortable, ahead of all things. This will help your confidence level, and to have fun, tremendously. The exception, of course, is if you are most comfortable in sweatpants and a "Naked Polo" tshirt and fipflops. If you are not a jeans guy, don't wear them. But I say, if you are, do - just a nice, dark pair. Similarly, if you dislike or are uncomfotable wearing tailored clothing (and many guys are), do not. But I digress. I don't know what city you are in, but here is a combo that rarely goes wrong. Grey or charcoal merino or cashmere pullover. I think that a mock neck (whether with or without a front placket) flatters most guys and is unlikely to be construed to be either too fashiony or too conservative. Brown corduroy or moleskin pants - again, classy, but more relaxed than wool pants, generally. The lighter colored the pull over, the darker the pants, and vice versa. Well polished brown shoes - no brogues - which despite their origins, are associated with businesswear, the actually shade being your personal preference: would you like to show off your shoes (tan to mid brown), or have them blend in more with your pants. I personally prefer boots (Chelsea or riding inspired) if not allowed to wear sneakers), and these are an option too. There are many, many options to look well groomed and put together without outshining the woman with an Attolini. Remember, a woman, like a man, is looking for two things: physical attraction and emotional comfort level. The first is not primarily a matter of what you are wearing, second, much moreso.