Reapplying Products Throughout the Day - Dry/Dehydrated Skin

Hi everyone! My skin has always been super dry but after looking at one of Picky’s posts on Instagram I think it also maybe dehydrated as well. I normally never get a lot of break outs but lately I’ve been getting more, and usually my dry skin is just a little patch or 2 on my face while now a days it’s basically covering my whole face (eyelids included! as well as being bad around my lips) So today I had a shower and have been reapplying one of the cream based moisturizers I have about every couple of hours. It seems to be helping me feel more hydrated and less dry but what I was curious about was if I should be washing my face each time I reapply. Does the 2nd, 3rd, so on time I reapply my moisturizer to my skin not work as well because the residue/moisturizer from the time before is still on my skin? Does this make sense? Am I overthinking this more than I should be?😅 Anyways just looking for a little advice and knowledge. If you’ve seen any of my past discussions you know I’m fairly new to skincare and still learning so bare with me if I sound sort of dumb right now because I’m truly just unsure And if you were curious about what Picky had to say on Dry vs Dehydrated skin I have the photos below so you can view it yourself!