How to step back and evaluate my wardrobe?

Pictures and a categorized list of everything that is in rotation (not being snarky; such lists are fun)

Organize your pants according to the following:

1. Dressier pants - wools, finer quality pressed chinos, etc.

2. Casual pants - faded & distressed khakis, more relaxed cuts, rougher textures, corduroy

3. Rugged pants - jeans, heavyweight outerwear, etc.

In the morning, grab a pair of pants according to the weather or your mood. Feeling like an adventurer? Grab those distressed dessert colored khakis. Cold? Get those cords.

Pick everything else according to the pant!

Jeans - engineer boots w/ a t shirt and leather jacket.

Slacks - OCBD with a blazer and loafers

And so on..

Match weight and textures. Heavy pants go with a heavy shirt and solid shoes. Distressed pants with distressed shirt and rugged shoes. Etc.

Select colors based on your skin tone and hair color. This will require a little research, not much.

Basing everything off the pant will give you a deeper understanding of clothing that will take you over the top! It is obvious, but it was a major breakthrough for me. I routinely look like a Ralph Lauren catalogue with little effort and I'm broke as hell. There is no limit to your variety once this is understood. You will no longer be tied to a 'uniform'.I hope this helps.

   I had a similar experience, though I have a particularity that makes this evaluation process much easier: I travel a lot. 

   This means that I have pack a lot and, while doing so, I can have a crispy clear view of what I have and of what I need.

   The problem is how to handle the "desires", those ones needs a much deeper thought process if you want/need to conciliate the needs with the wants.

   My advice is to pack for each season that you have to face, making a list is not visual enough for something that is purely visual (clothing), so you will be able to see exactly what you have and what is not covered.