I'll tell ya the "guy way" of doing it.
First off, a heterosexual guy needs a maximum of 3 pairs of shoes. One pair of good clean sneakers, a pair of casuals that'll match just about anything (for Vegas I *really* like Rockport for comfort and walking), and for dress up, one pair of dress shoes. If mixing colors, you need belts to match each (or do like GonZo and carry a white belt which matchs everything).
Heterosexuals also dont carry 3-4 bags. You get one huge fucking upright that is large enough to smuggle a small cadaver in and pack almost everything you own into it. Two pairs of shoes go in plastic bags in bottom of the suitcase. The other pair goes on your feet.
For a 5 day vegas trip, I check one large upright and cram all of my electronics, cameras, computer, etc into one other bag which is my carry on.
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