Shoe Dilemma

When packing for a vacation, at what point do you determine if you are taking too many shoes?
Tonight is my only chance to pack for the big BeNeLux trip, and I am rushing around making sure I have every little thing I will need while there. Having flown to Europe a few times in the past, I have discovered how much I truly hate being stuck in an airplane for hours on end. First, US to Europe flights are overnight flights- sort of. If you consider getting in a plane at 5 pm Eastern time, and landing at midnight Eastern time (7 am local), overnight. In other words, just about the time I should be getting tired for the night, its time to get up and get going. So I've tried the sleeping pill route- which is why I don't remember much from my trip to London. (I fell asleep in some museum place and my travel companions left me there and continued sight seeing. And never saw St Paul's Cathedral because I was so sleepy I couldn't climb the five berzillion stairs.) I tried the stay up all night the night before getting on the plane- and then ended up in a center seat on the flight to Prague, and couldn't fall asleep wedged between complete strangers for 9 hours. (And then was so cranky once I got to Prague that I actually started crying when I saw my meager motel room.) So I'm not sure what route I will take on this upcoming trip.
But back to my original problem. Shoes. It is imperative when stuck in one seat for 8 hours that you dress very comfortably, but more importantly, you must also be prepared for what meets you on the other side. I'm sure you are all envious, but the weather in Brussels is predicted to be a high of 40F, and snowy every day we are there. Which means I have to be dressed warmly upon landing, and the shoes must be good for snow. And don't even get me started on packing luggage and how to shuffle it from car to plane to train to metro and through a strange city. So right now I have the following on my bed waiting for me to decide if it gets to go to Europe-
My large pink fluffy boots- I think I will wear them on the plane, and bring slippers to change into. They should be good for arriving in Belgium and navigating snow. But they are large, and not necessarily great for sitting in for long periods. (Hence the slippers for the plane- for anyone who has never flown internationally- its normal and common for people to wear slippers on overseas flights.)
My sexy black boots- We do have some clubbing and after hours ambitions in a few cities. These are required accessories (to be worn with my faux black fur thingy). But they take up a lot of space, and cannot be worn for walking and sightseeing.
My favorite adored black Born clogs. These are the world's most comfortable shoes. I have worn them while standing on my feet for 8 straight hours and never even felt an ounce of pain. (Why do we say "ounce of pain?" We never compare it to say, "pounds of pain." I don't get it.) I love these shoes. BUT- clogs? Snow? I don't know. Not so smart. But if we're talking hours and miles of walking, these shoes rock. They are going for sure, even though I'm not sure why.
My other favorite Borns (have I mentioned how much I love my free Born hook up recently?)- ballet flats. I don't really have an outfit to wear them with, but just in case my feet hurt and I can't wear the boots, the flats become a necessity for dancing. These shoes are a pre-emptive strike so I don't feel compelled to buy more shoes while in Europe. (Oh that is a funny one. I'm making myself laugh! Me not buy shoes! Ha!)
Now, none of the shoes I have mentioned are really very good for sight seeing in snow and rain. So I have packed another pair of black walking shoes. They aren't Borns- probably Payless. They are decent shoes, and a pair I wouldn't mind getting ruined from all the walking. And if the weather is really bad, I'll have the pink boots as back up, right?
So 5 pairs of shoes. For a 6 day trip. There's nothing wrong with that, right?
And then there's the coat issue. Knowing that we will probably get wet and cold, I think I should take 2 coats. One coat to wear, one for back up. Right? But 2 coats? There is a luggage limit. Because using the back up theory, I also have to take 12 outfits for a 6 day trip. Which is why it has taken me 3 hours to pack so far...