He's coming down to Melbourne in a few weeks so I'll take him to Patrick Johnson and Azzaro to see if there is something off the rack that takes his interest.
Pink Socks - Edwins from DJs over the Christmas break, on sale were $125, down from $200 from memory. Best jeans I own, fourth pair of Edwins I have. Others were bought in Japan at an outlet type shop up in the mountains, $20 each and they are fantastic jeans from their vintage range, which doesn't mean much just that they looser fit and frayed ends.
Brownman - this might be of interest to you - http://www.ehow.com/video_4959573_marking-euro-hem.html
A euro hem is a convenient way to shorten jeans that are too long, since it uses the original hem of the jeans. This technique works best for jeans that have fairly straight leg openings, rather than flared jeans. You can hand-sew the euro hem or use a sewing machine. Many sewing machines have a toolbox on the front that you can remove so that the you can slip the leg of the jeans over the arm of the machine. This helps prevent you from accidentally sewing the leg of the jeans shut while sewing the hem.
Jobro - posted for the benefit of the context, not necessarily the purchasing recommendations. Am familiar with the limitations and pricing differentials associated with clothing here and abroad