Need Help Building A Shoe Collection

I'm trying to cover all bases with the shoe collection I'm building and right now and need your view, Thanks to the info from SF, I have the following shoes (all but the Topsiders were acquired in the last month or so :) ):

• Black captoe oxfords (C&J Connaught),
• Chestnut single monks (C&J Monkton),
• Black chelsea boots (RM Williams),
• Chestnut chelsea boots (RM WIlliams),
• Dark brown suede chukka boots (Florsheim which I bought just before I started looking here so too new to replace),
• Blue suede skate shoes (Dekline Santa Fe - http://www.skaterhq.com.au/browse/details.asp?ProdID=143195)
• Dark brown Sperry Topsiders (too big so will be replaced at some point)

I'm 43, in Australia and wear a suit (either navy or gray) to work 4 days a week but I'm in IT so pretty much anything goes (all of the top 4 can be worn with either suit). I wear the chukka boots and skate shoes with jeans and chinos. For shorts, I also wear the skate shoes.

For the weekend (ie. not with a suit), would a pair of burgundy/oxblood/dark brown penny loafers cover any situations that the set above would miss or is there something else I should consider?

I've been looking at the dark brown C&J Sydney, a burgundy C&J Boston or Harvard for this. An Alden LHS would be interesting too but I've haven't got a clue on how to get the right size for that one.

I've read through some of the threads in the forum and it appears I have most of it covered. I do like the look of burgundy/dark brown penny loafers with jeans or chinos.

Your thoughts and advice are much appreciated. 

Thanks,

Gerry