I'm #3.
"If your second toe is longer, you're a born leader. You're great at managing people and coordinating efforts. You're energetic and resourceful and stand up for what you believe in. If your second toe is shorter than the others, it means you may have trouble standing up for yourself, though you are more level-headed."
http://www.higherperspectives.com/toe-length-personality-1593182514.html
Guess mine are closest to number two. As far as what it means? I haven't a clue. Maybe from wearing combat boots so many years. IDK
This type of foot or toe, i.e. Morton's toe, is also called the Greek foot:
https://en.wikipedia.org/wiki/Morton%27s_toe
And it is true that a pair of suitable new shoes, which do not hurt after walking for 20 minutes, is really hard to find.
I never had a problem, but my index toe is only about two or three millimeters longer than my big toe.
That is lucky - on my side, new shoes were often a torture, and blisters were frequent.
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