Different methods work for different people in different situations. If Kon Mari isn't working for you try something else. Personally I have good success with a 'fixed amount' approach. I ask my self how much space I'm really prepared to dedicate to this group of things, or how many I really need, and then only keep that much. You've already decided that you want everything to fit into a dresser, that's good. Now break it down by category. How many outfits do you really need for whole foods? 2 or 3? Pull them out and put them aside. How many "playful" outfits do you really need for photoshoots? 1, or 2? Put them aside. How many business casual outfits do you need for shows? just one in neutral colours so you can jazz it up with accessories? Put it aside. Now move onto your general clothing. I find I already pretty much know which stuff i wear regularly but just hold onto everything else for one reason or another. Pull out only the stuff you know you wear regularly (should be no more than say, 10 tops and 10 bottoms) and put everything else aside.

Now put your 3 Whole foods outfits, 2 playful outfits, one business outfit, and 10 every day outfits into your dresser. Do they fit? If not you're going to have to either use more storage or cut back some more. If they do fit and you have heaps of space left you can 'rescue' a few things from the left over clothes, or leave the space for future purchases.

Another way I've done it is to remove all your clean clothes to a seperate place, and only put them away after you've used them. In a few weeks you can get rid of everything that's not put away because you know you don't really use it.

If you have trouble with motivation break it down. Use 20 minutes of work, then take a break. Or just do one drawer, then take a break. Have a set time amount for the break so you get back into it.