SHOES FOR THE SHORT DUDE-What is the best shape footwear for the vertically challenged?

I'm 5'5" and you know what? It doesn't make any difference. You wear good quality clothes and shoes in coherent combinations that fit properly, you look good. End of story.

I'm about your size, with small feet (size 6), and I tend to think that more substantial shoes look better on me as well (say, Florsheim Imperial Longwings).  I think it may be because it makes my feet look more "normal" sized.  I have an older pair of J&M cap toes which I rarely wear because they look so stubby by comparison.  

 

On your other rules: (1) I think monochromatic colors help; (2) I don't think no cuffs helps much - maybe if you are 5'7 trying to look taller, but I don't think there's much difference under 5'5; (3) pants should have a slight break, but too much is as bad as too little; (4) I'm not sure that vertical stripes help, but horizontal stripes are *horrible*; (5) I don't know if slimmer tailoring and shorter rises help by themselves, but they tend to make the suit look like it fits better, which is important: the last thing you want to do is look like a kid in your dad's suit.

 

Additional tricks - get MTM shirts with 2.5" collar points (3" seems to be standard) - this fits my face much better (if you get a buttondown shirt, just use the standard size; it's fine for some reason).  This is less of an issue now that narrower ties are becoming available, but when the standard tie length was 3.75", I would try to find 3.25" or 3" ties - it just looks more proportioned.

enofile, I presume you also have small feet. If you go with burly shoes like double-soled gunboats, you will end up looking like member mafoo, whose legs look disproportionately large when compared to his psysique. Yet very contoured shoes like those made by G&G will make your feet look even smaller than they are. My recommendation is to between these two far-ends, but with lasts that are a bit longer and wider to make your feet look larger. Alden is the answer.

LOL

For the smaller gents, my advice would be to avoid shoes featuring an outrightly round toe box unless necessity demands it. Proportioning is what matters. You can have the acceptable appearance of larger feet with a slightly narrower pant leg and no cuffs. This means avoiding the recent trend of the 2" cuff which works better on taller gents. At a height of 6 ft myself, and I have stated this before, I would truthfully be much happier at 5'-6". Aside from being able to change light bulbs easier, being taller isn't always better, at least not in my own experience.

enofile you seem well-adjusted to your body type and this is pleasing to read that you embrace life with humour.
Here is the Alden Lasts chart. Plenty of nice toe shapes to choose from. (Right-click 'open in new window' to see full size image) Alden Last Chart (Click to show)

Shoes that fit properly are more important than obsessing about any irrelevant advantage one "shape" of shoe might have over another. I doubt that there are any but doubtless some will think to the contrary.

True, GBR, no one is likely to argue that a shoe's shape is more important than how it fits, especially considering what ill-fitting shoes can do to one's comfort, posture, and health. That does not, however, make a shoe's shape an "irrelevant advantage." I'm sure MoL was assuming proper fit when he offered his excellent advice: