Are you in or out?

A debate was recently brought up between the staff here at The CuffLink (all 2 of us!) while on vacation with friends in tragically rainy Rehoboth, Delaware.

cheap sneakers shoes for women & men,cheap dresses 2011 for women Are you in or out?
Kenneth Cole boots w/ pants tucked in

I have a pair of tall leather shoes for men that I love and I was going to wear them one day, but I had a question.  'Should I wear these with the pants tucked in or out?'  He suggested that I tuck them in and show off the boot, but you know how you that thing where you ask advice and then do the exact opposite?  Guilty.  I mean, it's not like we were going out somewhere special ' just shopping.

cheap sneakers shoes for women & men,cheap dresses 2011 for women Are you in or out?
Kenneth Cole boots w/ pants untucked

So I untucked the pants and followed my 'subtle style' rule once more.  But this got me thinking: is there a fashion rule somewhere akin to 'no white after Labor Day' that says there's one sole way to casually wear men leather shoes?  Or is it open to individual interpretation?  Are there only certain venues where you can wear a certain style?  So many questions!  Hopefully you can help me out.  Let us know which side you take in this debate.  Pants in, out, or either way?  Let us know in the comments and vote in our poll (both here and on Facebook).

Article Source: http://www.shoulderbagss.com/men-women-shoes-heels-boots-dresses-are-you-in-or-out