I would skip the black captoe.
As far specifically where to look for quality, sleeker shoes, I would take a look at crockett jones mail order (from UK - mail order has more selection than pediwear and the CJ website.) Pediwear.co.uk and bodileys of northampton both have terrible stock shortages right now. Find out how your foot fits the 341 last. You can mail order a pair of Crockett Jones on the 341 from Barneys and keep them or return them (there is about a $100-$150 cost to buy them at barneys over and beyond what you'd pay ordering from overseas - but time, ethical etc considerations )
Also, get a pair of alden shell cordovan shoes. Not a ton of variety, and also not the sleekest, but it's a beautiful, long lasting, unique thing to have.
I'd look at these based on my preferences (in no order)
1. CJ westfield dk brown
2. CJ finsbury chesnut
3. Alden Men's cap toe color #8
4. AS Exclusive Range Moorehttp://www.afinepairofshoes.co.uk/co...moore-chestnut
5. Alden NSThttp://www.theshoemart.com/alden-men...deen_last.html
6. CJ Arden Tan
7. Peal Split toe Brown (buy on sale for ~$370)http://www.brooksbrothers.com/IWCatP...tionsize=#null
8. Crockett jones Malvern or a 3 eyelet plaintoe blucher (if you don't want to go monk)