I spent this morning packing to go to a funeral and it took me significantly longer than I expected. I knew that I had plenty of somber pieces, but it had been awhile since I had looked at many of them, so my memory of them turned out to be fairly skewed. The black jersey wrap dress that I pulled off the hanger showed too much cleavage, the black patent heels felt unsupportive after months wearing boots and booties, and I struggled to find a sweater and pant combo that didn't look casual. My wardrobe is extensive enough that I was able to create two outfits, but not with the pieces I was expecting to use.
Luckily I am in the habit of trying on my outfits while I am packing a suitcase because my weight often fluctuates and I don't want to end up at my destination with nothing to wear. But whether you try on the pieces while packing or once you arrive, if your closet isn't offering the options you remembered it having, you are going to be in trouble. Any last minute shopping trip is going to force you to choose within a limited selection and will likely result in you paying more than you want for pieces that you are only lukewarm about.
To ensure that your wardrobe is always well-rounded requires doing an occasional audit:
1. Take the time to try on all the pieces that you don't wear on a regular basis. You can do a massive try-on session one afternoon or you can try on a few pieces a week. This will ensure that your memory of the fit and style of the piece is accurate. It's difficult to really assess an item when it is on the hanger, so give yourself a visual of what you look like in it.
2. Keep a list in your closet of pieces that would be great for different occasions. If you try on a pink floral dress and think, "This would be perfect to wear to a wedding!" then you should make a note of that. This could be as low-tech as taping a piece of paper to the inside of your closet door. Then when you need to attend a wedding, you can check your list and start by trying on the pieces you know will be winners.
3. Get rid of the pieces that aren't carrying their weight. For example, you might have a Little Black Dress that you don't actually like wearing, but you keep in your closet just in case. There are other LBDs that you do like and would wear more often, but you feel like you can't buy them because you already have one. Donate the one that you don't like (and aren't wearing) and use that space in your closet for something that you feel great in.