My current everyday shoes are about to die. I have only recently made any sort of attempt to be fashion conscious and have lurked here for a while, so bear with me. I am currently in graduate school, so there is no need for the shoe to be particularly formal. In fact, pretty much any kind of shoe that is not a sneaker seems to be considered formal by grad student standards. In starting the search for new boots, I found myself unsure as to what kind of boot would be appropriate for my environment: chukkas? dress boots? work boots? I know leather soles are preferred, but as a commuter, I have already eaten “it” several times walking on the sidewalk in leather soled shoes during winter, so I would definitely prefer a thin profile rubber or composite rubber/leather sole. I generally wear jeans (and on occasion, corduroy or khakis) with a button down shirt (or fleece in the winter). Despite my confusion as to what kind of shoe is appropriate, I do have a certain aesthetic in mind: a brown, finished leather boot which covers the ankle and has a rounded, but sleekly tapered toe. I hate wingtip brogues, but like quarter and half toe cap brogues. I would definitely like to avoid Chelsea boots. Likewise, I am not a huge fan of the workboot studs, but am willing to compromise there. Finally, the sole really can't be leather, but many of the rubber soled work-like boots have huge profile lugged soles, which I don't like. As for full height vs ankle, I would prefer ankle, but would be fine with a full height boot. My search yielded a number of results and was hoping to get some comments/feedback on their style, suitability to my needs, and durability.  These are nice, and are a nice compromise between the studs and style (in my mind).  These are nice as well, but I am not sure about the monk strap and somewhat square toe. I know that most people here tend to think that  Stafford shoes tend to be of lower quality. I don't think that  imitation leather is a good idea.  These have been debated on this site a bit, but they are I was hoping to avoid such obvious studs. The overall boot looks pretty good though. I also found a couple of chukkas which meet what I am looking for a bit more.  These Timberlands look pretty nice, but are out of my price range. I also started looking at chukkas. Most I had seen were a bit too clunky for what I wanted, but  this pair and  these look pretty good as well. I know that I am a bit all over with styles here, but that is a function of me not knowing what is really appropriate and just going on overall shape of the boot. Edit:I suppose I should note that I am also considering cowboy boots, but those generally seem out of my price range unless I look to ebay (I am not a huge fan of no returns on shoes purchased online). Edit: I didn't even know that Caterpillar made  boots.