[1] http://www.amazon.com/Anytime-Tools-Shrink-Sleeve-Assorted/d...
I've found that 3/8" heat shrink fits over the connector, but 1/4" does not. But the 3/8" (at least for the brand I got) does not constrict down enough to fit tightly on the think cable. So I bulk up the cable with 1/4" silicone aquarium air pump tubing.
Instructions: Cut one ~4" piece of silicone tubing, slit lengthwise, and put just below the connector. Cut another ~4" piece of silicone tubing, slit lengthwise, put over the first piece of tubing with the slit on the opposite side. Put this second piece slightly higher, so "top" of tubing covers the base of the connector, and the "bottom" of tubing is ~1/4" shy of the inner layer.
Then cut a piece of 3/8" heat shrink to ~4.5" long. Slide the heat shrink over the connector on to the two layers of silicone tubing, so the "top" is tight to the L of the connector, and the "bottom" extends just past the farther (inner) tubing. Then shrink the tubing with some appropriate heat source (or carefully shrink with an inappropriate source like a match or lighter).
If you're rough on your gear (I've thrown my laptop into a TSA container in a 5:30AM grog more times that I can count), I'd do this as a precautionary measure even if you don't see any damage yet. It might not look pretty, but functionality over form any day.
[1] combined with using thin wire shielding in order to maintain a 'sleek' aesthetic
I think you are visualizing it correctly. Let's see if I can replicate it with ASCII art (not to scale):
------------------------------
==========================******************
=========================*********************
++++++++++++++++++++++++++++++*********O********
=========================*********************
==========================******************
------------------------------ ****************
****************
- layer of heat shrink ------- Rigid Connector
= outer layer of silicone =******************
= inner layer of silicone =********************
+ Thin frayed Apple cable ++++***color O led ***
= inner layer of silicone =********************
= outer layer of silicone =******************
- layer of heat shrink ------- ****************
****************
It comes out looking quite nice. The rigidity of the tubing plus shrink wrap isn't a problem if you plug in so that the rigid part is along the side of the laptop. It actually provides a fairly nice handle for unplugging, since you can get good leverage anywhere along the shrink wrapped portion.