About 4.5 years ago, I cast off my corrected grain Kenneth Cole New York shoes and began the upgrade process. Like many new to SF, I've made many mistakes along the way while figuring out my size and my last preferences, having bought then sold seven pairs along the way to get to what I have now.

Top L to R: bal boots from Zee's HK, John Lobb Tudor, John Lobb Newland
Middle: Trickers Henley, Allen Edmonds Jackson, Santoni Brenden
Bottom: John Lobb Stafford, Santoni Bristol, Santoni Jensen
Only the AE Jackson and Santoni Jensen have rubber soles. The bal boots and the Trickers have Topy. I have lots of balmorals, so I figure my next pair should be a brown wingtip blucher with rubber soles for bad weather. I was thinking Alden but they seem a bit boring/"old man" to me.
Suggestions for my next pair? Budget is $250-$500, live in Washington DC, prefer to purchase in store or online w/ returns. I'm not really into secondhand nor loafers/slipons though the EG for RLPL Eden interests me.
Also, which of these work well with jeans (or suggest a new pair that does)? Thanks.

Top L to R: bal boots from Zee's HK, John Lobb Tudor, John Lobb Newland
Middle: Trickers Henley, Allen Edmonds Jackson, Santoni Brenden
Bottom: John Lobb Stafford, Santoni Bristol, Santoni Jensen
Only the AE Jackson and Santoni Jensen have rubber soles. The bal boots and the Trickers have Topy. I have lots of balmorals, so I figure my next pair should be a brown wingtip blucher with rubber soles for bad weather. I was thinking Alden but they seem a bit boring/"old man" to me.
Suggestions for my next pair? Budget is $250-$500, live in Washington DC, prefer to purchase in store or online w/ returns. I'm not really into secondhand nor loafers/slipons though the EG for RLPL Eden interests me.
Also, which of these work well with jeans (or suggest a new pair that does)? Thanks.








