I have a number of constraints which dictate everyday toddler wear.
1 Money. I can't afford to keep replacing clothes that get irrepairably stained, torn, or worn out from too much washing. So I wear cheap shit that doesn't matter. Some of my cheap shit is more stylish than others.
2 Shoes. I can't wear heels, at all, ever, so they have to be flat. They have to be easy to clean mud off so they don't get ruined. See point (1). I have big calves, and hideous legs, so boots and skinnies or short skirts and tights are out.
3 Requirement to sit on the floor a lot, in public. This, combined with fat legs, also rules out skirts. It means jeans plus top or leggings plus jumper dress. Due to repeat floor contact, lots of washing. See point (1)
4 DS's stuff is in a boring rucksack because it's easier to carry when I also have to carry him, and DP is willing to carry it. Transferring everything into decent, stylish bag and back again every other day will result in the thing I need being in the other bag.