JR -  I'm sure you could write a book on what types of shoes to buy but I'm looking for some wisdom for someone in my position. I have three pairs of leather shoes I wear to work. Cordovan wingtip brogues, cap toe black Allen Edmonds lace ups, and old Church's brown leather loafers (my favorite simply because the leather is the softest and my feet stay cooler). Found from thrift store, ebay and ebay respectively. To simplify, I really want a pair of suede desert boots for the summer. Should I roll with Clark's, or step it up with a better known shoe maker?

IG - It sounds like you've got a good start on your workwear footwear.  Cordovan, Allen Edmonds and Church's are great foundational options.  However, it sounds like your casual footwear is lacking.  Desert boots originated in hot and humid climates of Africa and the Middle East. Characterized by their minimalistic silhouette, crepe sole, and simple four eyelet lacing they are a great way to wear boots during the summer and still look relaxed and put together. The unlined, suede versions are best in our opinion.  Clarks is the manufacturer of the original desert boot and is the gold standard by which all others are measured. However, they aren't the only option available.  There are several others that are just as wearable and affordable. Check these out.