I know what you mean. You are not crazy, nor the only one with this issue. My son is 5, too and last year it took us 2 and a half HOURS to get him dressed, just dressed, for preschool, every morning. And he would ONLY wear certain jeans, and one of two hooded sweatshirts. That is not the case anymore, he has very few clothing issues anymore, but it did not go away on it's on, we did A LOT of work!
I'm not saying, in any way, this is the case for you - my son has Sensory Processing Disorder. Go to this site and review the checklist for your child:
http://www.sensory-processing-disorder.com/sensory-proces...
When I did that the first time, it was a real eye opener the beginning of things getting better. I had only barely heard of it, and did not understand it. When a friend's mom, retired, but worked with kids her whole career, watched my son for all of 15 minutes, she pulled me aside and said "fill this out and call your doctor for a referral for sensory integration therapy".
My (former) family doctor, did not "believe" that Sensory Processing Disorder was "real", because it is not currently listed in the official diagnostic manual that psychologists use. The occupation therapy field has entire schools for this! It took time to find therapists to help, resources are limited, but there is so much you can do on your own!
Email me if you have any questions