And I just can't get into the idea of wearing used shoes.
I was totally with you until recently. I've picked up a couple of pair of used shoes on ebay. To be sure, these aren't shoes I want new, they're old dress shoes I intend to wear with jeans.
I made sure they were in relatively good condition before buying (I've seen a lot of thrift store shoes that look OK but have mold/mildew or other grossness--needless to say, I'm not buying those). I gave them a good cleaning inside with disinfectant spray (lysol, IIRC--and I use it liberally) and a paper towel. I tree them for a day or two. I also buy new full footbed insoles. Even trying on shoes with someone else's footprint inside creeps me out, and insoles make a big difference.
As for head to toe vintage, the esquire guy looks good, but you have to be committed and a real character to pull that off.