I think this depends a lot on whether you are also working on smithing and enchanting. I have 100 smithing and about 90 enchanting, and it's incredibly rare for me to find pieces of armor that are better than what I can make myself. I'm a light armor mage and I wear a full suit of custom-enchanted glass armor. I also have a full set of legendary dragonscale, but it's not enchanted yet because I'm waiting to hit 100 before I do so. I used to wear Dark Brotherhood stuff, but it just couldn't keep up with the vastly superior protection that my legendary glass armor has. With high enchanting, you can also make sure you get exactly the enchantments you want, instead of having to decide between less optimal protection for more preferable enchantments.
The only exception I've found to this are a certain set of masks that I won't discuss further due to spoilers. Those things, with smithing improvements, are absolutely superb.
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