Compared to large and colorful butterflies like swallowtails and Monarchs, skippers are usually difficult to identify. Even so, they are easier than most of the moths that I find, but they are still tricky. Consider the skipper pictured above. It is small, brown, and has almost no distinctive markings. I think that makes it a Dun Skipper (Euphyes vestris), but it is difficult to be sure with such a plain butterfly.
This one looks easier to identify, but that did not stop me from misidentifying it at first.When I first looked through my butterfly guide, I thought it was a Sachem because none of the others seemed like good matches. Thanks to some of my Flickr contacts, I found out that it is actually a Broad-winged Skipper (Poanes viator). What threw me was that my guide's images seemed to show a much brighter and more contrasting streak down the middle of the hindwing. Apparently the hindwing can look plainer, as this one does.
I liked this view of a Broad-winged Skipper feeding on phlox.
Luckily not all skippers are quite as difficult. The one above was a new species for me but fairly easy to find in the guide. This is a Peck's Skipper (Polites peckius). This one was tiny, even for a skipper. You can see how small it is if you compare its size relative to the flowers to the Broad-winged Skippers above.