Most 2-year-olds are ready to try getting into their clothes all by themselves. To help encourage these early attempts:
Pick Velcro and elastic.
Skip shoelaces and buckles for now: Velcro tabs are the simplest for little fingers. And go for pants with elastic waistbands; your child will be much more successful if he doesn't have to fight with buttons and zippers.
Prep his shoes.
Pull up sneaker tongues and loosen shoe straps so they'll be easier to put on. Also, use a permanent marker to draw a star on one of his shoes, and teach him that the marked shoe always goes on the same foot.
Offer a demo.
Show your child how to sit down to put on his pants -- it'll be easier than if he tries to balance on one leg.
Use a new tack.
If he's having any trouble pulling a sweatshirt over his head while groping for armholes, try an open-front top. You'll have to work the buttons, but he'll also get practice putting on a jacket.
Indulge wardrobe whims.
Though your daughter can't don her tankini for a trip to the grocery store, she may be more inclined to dress herself if she can choose to wear some beloved items occasionally. So allow her to wear the swimsuit under a dress.
It takes time to sort through the mystery of left versus right and top versus bottom. Give your child an extra minute or two to figure out what should happen next, but make sure to step in whenever he gets tangled up or frustrated. The goal is to foster independence, not to force it too early.