I wonder too if men just don't have much inspiration in their lives about how to dress? And like us, if they see pictures on blogs...or better yet, be around some fashion forward guys...and actually try on some clothes that fit well, they can easily be converted.
When my son was here visiting from Toronto...he's 27...I showed him some of the Street FSN photos of guys outside of the fashion shows in Milan (that I think Jonesy had posted in favorite links?). Since he has tattoos too, he liked seeing the inked arms paired with dressier outfits...and also, just the way the men seemed to carry themselves with such confidence. He always looks stylish in his slim cut Lev's and great fitting dress shirts or t shirts..and Converse or Blundstones in winter. We had a great time shopping together.
This year he got a great Filson jacket at Blackbird in Seattle: http://www.filson.com/products.....oduct=1011 My experience with my sons and with my husband is that they prefer the go once a year and stock up method. Doing some research ahead of time...like I'd done for him with the Filson jacket...helps because it seems they like to get in, get their stuff and get out of the store!