Having deep set eyes means that one has permanent dark under-eye circles. It has nothing to do with lack of sleep, alcohol consumption and general hydration (though all of the above can make things even worse). It's just the way one's bones are structured in a way that creates dark shadows under the eyes. As my tecchie friends say, it's not a bug-- it's a feature. Thus, there's only so much you can do to lighten things up; it's another way for me to tell when a makeup artist knows what he or she is doing. Recognizing that piling up thick concealers is futile, and instead using highlighters and correctors in a skin-friendly texture is the only way to go.
Giorgio Armani Master Corrector and High Precision Retouch Concealer are liquid, light and very blendable. The textures don't cake or pool in those fine lines you weren't fully aware even existed (denial. Never fails). I use Giorgio Armani Master Corrector in no. 1 and High Precision Retouch Concealer in No. 3, and usually mix them together. They create a concoction that helps even out the problem area. These corrector and concealer meld and disappear seamlessly into light texture foundations.
It's important to note that neither the concealer or the Armani corrector provide full or even high coverage. They blur imperfections and shadows but don't make them go away completely. For a superb texture and serious coverage I recommend Ellis Faas, but if you're searching for the most natural looking textures and a very light touch, give Giorgio Armani a chance.
Giorgio Armani Master Corrector & High Precision Retouch Concealer ($36 each) can be found at select Nordstrom, Saks and from Barneys.