I would lay out a couple of choices and let my son pick what he wore that way. It sped things along and gave him the sense doing it all on his own. It also let me pick a couple of things which were interchangeable aesthetically – which seems to have taught him a sense of style.
But, like you, I preferred to let him do things himself – which often meant letting him run to things that terrified me. It meant letting him take that tumble climbing rock piles or chasing fish in the stoney creek. Letting him learn the spinning out trick on the kids' Typhoon Trike saw me in tears watching him; and it meant cleaning him up after he crashed and skid to stop by skinning his leg from lower thigh to upper calf. It meant watching him learning to skateboard or ride his bike down the hill in front of our house – where even the dayworker construction guys watched with baited breath as the neighborhood kids took that hill at speed. The hill ended at my front yard, with no deceleration grading at all.
The result is that he's chosen a career in EMS and it's absolutely terrifying. Think, Nick Cage in Bringing Out the Dead. My son sees that as a roadmap to his future as a paramedic.
That's always been my "most annoying thing about being a parent" – standing back and letting my son rush headlong toward the scary arguably dangerous stuff.