Jimmy is a headstrong little boy, has been since the get-go, and we deal with it by letting him have his way when it is safe for him to do what he wants. And this extends to clothes.
We started by offering him a choice of two tops, followed by two pants, and we would ask him to choose which one he wanted to wear. And it worked for a while: getting him dressed didn't take too long, and he could feel he had some say in the matter. Win-win.
Some days the result was rather coordinated and subdued, and on other days the result was fun and loud.
There would be occasional day when we might ask Jimmy what colour top he wanted to wear. He would say "green!" because it was the colour he could say at the time, so we would get him a green top.
"No green top!"
"What colour top do you want to wear?"
"Ok, here's a blue top."
"No, not that blue top."
This exchange would continue another round or two or more, usually ending with Jimmy actually wearing an orange or red top. He may or may not have actually wanted to wear the orange or red top, but after 5 minutes going through each and every top in his collection, and explaining that the other red top was dirty and in the wash, we had to settle for something.
So, these days Jimmy mostly chooses his own clothes. This results in some interesting outcomes. He's a toddler and it's allowed. Actually, I think it's expected. The photo at the top of this entry shows three outfits and the ones on the left and the right are ones I had picked out for Jimmy, a few days before taking the photo. The outfit in the middle is all Jimmy. Clearly that lovely warm jumper is a "top".
Jimmy likes strips, bright colours, prints, and anything with pockets. He's not afraid to wear red with coral, he doesn't mind if his pants are turning into capris, and his go-to shoes are his dinosaur
gum rain boots. He's quite happy to wear his rain coat when it's cool and windy, but he doesn't like how his hat flops over his eyes.
I'm not beyond vetoing Jimmy's selections. The lovely warm jumper? Vetoed - Jimmy would have been far too hot that day. But for the most part, Jimmy has pretty good taste, even if what he wants to wear is not what I would have picked. And that's ok, because he's allowed to dress however he wants - he's the one wearing the clothes.