Well, is the Bleeker St a seasonal shoe, really? Is it all that bad to have a Brogue Suede Strand? If the weather is too bad to wear these, I'm wearing boots anyhow.
But yes, I've fallen into the trap of buying a bunch of low-priced seasonal or conditional-use shoes. However, I'm not convinced yet that it's so terrible. I don't go into an office regularly, and if I did, it's casual. I know that I"ll wear loafers and boat shoes all summer and boots all winter, and any other shoes I buy should be suitable for spring and fall.
The Long Branch is different, yes, but some of us don't dress up as often, or look forward to doing a reduced-price MTO.
How many pairs do you have? I think I have enough dress shoes for work even though I can pretty much get away with casual. However I like to dress up sometimes and I'm going to buy the carlyle for a nice sleek black pair.
I try to balance dress shoes and casual shoes so I have a good balance