Alright, let me chime in.
You need two pairs of shoes no matter what. The leather must rest after each wear. Rotate the shoes, allowing the other pair to rest with a shoe tree after each wear.
Invest in your shoes now, instead of buying pair after pair of crap shoes. A $300 pair of shoes will last you 3-5 years with good care and sole protectors.
You need to look for full-grain leather, not the plasticky top-grain or corrected grain shoes. Full-grain leather will last much longer as it will not crack. Also, ensure that the soles are welted (goodyear or blake). I prefer goodyear welt, but blake is also ok.
Some brands you can look at are
- Clarks (you need to make sure that shoe is welted, and not corrected grain)
- Loake (I can only recommend the 1880 range) - Available from Herring Shoes or Pediwear (Free shoe trees from Pediwear)
- Herring Shoes (House brand of Herring Shoes but made by Loakes anyway) - Use code HSAB for free shoe trees
- Allen Edmonds (Excellent quality, but you need to look for seconds sales, which I can't be bothered. Also you have no way to try on your size unless you are very very sure on the size)
- Johnston & Murphy (A lot of their shoes are corrected grain but they are mostly goodyear welted, so take care when you buy)
You can try Loake (and Herring Shoes as they are made by Loake) at Robinsons & J&M at Taka.
Even if you don't want to pay so much for shoes now, at least get 2 pairs of shoes and rotate.