What sort of dress you choose is going to depend on your lifestyle and the events that come into it. You must be honest with yourself. While your pretty dress can go to church or date night or most parties, only you know which you spend more time attending.
For instance, I attend a very casual church, but I go out to dinner with my husband quite regularly and we almost never attend dressy parties. Therefore, my “pretty dress” is going to be mostly a date dress. If the situation was reversed, and I attended a church that still dressed up, I would have a nice quiet dress that I could sparkle up when we went on the town. Likewise, if we went to a lot of parties, I would choose something that could be accessorized with endless variety (the classic LBD*). My really dressy dress stays in the closet most of the year, but it’s stunning and I love it.
Your special dress should be fit you perfectly. It doesn’t have to be a “timeless classic” unless you’re spending enough time in it that you’ll be recognized as wearing the “same old thing” over and over. (Timeless classics, like LBDs, can be accessorized so as to not be obviously re-wears). Wear what suits you, and what you love. A pretty dress is exactly the right place to indulge your heart.
*The LBD doesn’t have to be black! It should be a basic neutral, suited to the dominant season in your area. It should fit and flatter you, which may well let out the slim sheath dress that has probably popped into your head at this point.
**You may substitute in your white blouse and dark skirt until you are able to find this special item.