I took the iPhone plunge in early 2009, getting a 3G a couple of months before the 3GS came out because my old Motorola Razr died.
I knew I needed to get a protective case for it because I’ve had previous phones meet their demise due to repeated drops, a couple of friends with iPhones have dropped theirs and cracked the glass, and, well, it’s the most expensive phone I’ve ever bought.
Dave (boss, colleague, friend) solves this with a belt case, but I have long been opposed to the concept of the Batbelting of geekdom. I like to carry my phone either in a shirt pocket or in the front pocket of my pants.
My first case, purchase when the phone was less than a week old, probably, was an incase Slider. The case served me well with my only complaint being that the lower, smaller part of the case that was intended to slide off for docking more often stayed put while the larger part slid off. This wasn’t usually an issue because I don’t have a dock that requires removal of the small part. The case also started to lose its matte finish over time and became speckled with shiny spots.
My second case purchase was an Aquapac Waterproof iPhone case. I bought this for kayaking and other water sports after having a good experience with an Aquapac camera case. The iPhone fit is a little tight, but the phone can be fully operated inside the case, which allows texting and checking the weather while paddling (or during a rain-drenched football game).
My most-recent case purchase is an OtterBox Commuter TL (in blue). This is a two-part case consisting of an inner, colored silicone jacket that is nicely textured for grip along the edge. The jacket incorporates shock-absorbing coring to protect the phone from drops and has covers for the dock, headphone jack, and button covers to help keep dirt and moisture out of the phone. It is not, however, a waterproof case. The second part of the case is a hard, clear plastic spine that provides extra protection for end drops and covers most of the silicone to make getting the phone out of a pocket easier than with an all-silicone case.
My only negative (barely) observation so far on the Commuter is that the plastic spine has less friction than the Slider on hard surfaces like desks, dining room tables, and nightstands. As a result, it tends to slide around when I’m trying to type on the phone at my desk, for example.
The Commuter is also thinner than I expected. I was worried that it wouldn’t fit into the Aquapac case. I was wrong (though either case is easily removed). I’ve tried it once and it may slide in and out of the Aquapac more easily than the Slider due to the low friction of the plastic spine, apparently.