I know I'm risking sounding like a huge control freak here, but I'm going to admit this anyway: last week I organized the little guy's closet into outfits.
(Far left are church/dressy clothes, middle is "everyday" and the right are sweatshirts that are multi-outfit appropriate.)
I was out shopping (the same time I picked up the curtains), and as often happens to me, I drew I total blank on what I needed for DS. "Make a list!" you say. Well, yes, sometimes I do, but I always forgot to write down exactly what he needs and (more importantly) in what colors. So standing in Old Navy, staring at toddler boys' sweatpants, I vowed to go home and organize his closet into outfits and his drawers into "extras" for those inevitable times that he spills water, or plays outside, or wipes sauce on himself. I did just that, and on my next trip out, I was able to pick up a few extra pants and shirts (in several different color schemes) to match everything in his "every day" rotation. Whew.
I feel so much better now and dressing him has become much easier. The bonus is that now DH can dress him without worrying about putting clothes together. I imagine this system will be even more helpful in the future should we have more children. Oh, and from now on, I'm only buying clothes in pairs. Same rule applies to hand-me-downs. If we don't have shirt or pants to match the item, it goes.
Oh, as I was editing this post, he just dripped most of his water bottle down his sweatshirt. Sigh. Good thing I know exactly what I have on hand (and clean) that he can wear next! And I took the water away!