Nice effort, back leg is a bit of distraction.
I am not an expert in portrait yet but I agree with John about the legs. I am glad you are moving forward with this and not lacking for models to pose for you...
I think your fill light is over powering everything. I'm not sure what your goal is but she looks like she's more interested in selling the leather jacket on ebay. Other than the lighting, I think she needs a bit of warmth in her skin tones.
I use to do some retouching for JC Penney's catalogs. The emphasis was always on the clothing and I often had to desaturate the skin tones of the models to force them into the background. Your photo reminds me of that.
I think this is an example of where cloning is preferable to cropping which would have her hand too close to the edge of the frame. Though a tash tricky with her shadow and that of her lower leg. Very nice altogether though.
An interesting lighting and PP treatment for a woman; the harsh lighting and high contrast look tends to be used for male models. On the other hand, it works well with the leather look.
Travis, would your first image be an example of flat lighting? I recently had a portrait done, and I believe that's what was done to me to hide any sight of a wrinkle. I know your model doesn't have wrinkles....
Very different look, nice capture. Is that shadow near the blouse from subject movement, all the other shadows are subdued?
Travis - one thing that I noticed about both of your shots is that Jess has her eyes positioned so that they are pushed to the edges of her eye sockets. That tends to make for a strange looking image. I suggest you might try to get her to look in a direction where she is looking more or less straight ahead so that you get the iris more centred and show the whites of her eyes on either side for a bit more balance.
I found when I started doing that, my people shots looked a lot better.
I don't shoot portraits but I do view them. My impression is that the relative position of the iris (centered or not) is purely a personal preference.
I just now quickly reviewed the photos of 13 famous photographers ranging from those living now to those who lived in the 19th century and quickly found examples by all of them of photos made with the iris centered and other photos made with the iris far at the side. Some of the photographers are known almost exclusively for their portraiture. The portraits (some were perhaps candids) were made in a wide variety of situations ranging from formal studio portraiture to portraits made outdoors or at work. Some of the photos of the people with the iris positioned strongly to one side are on the covers of books.
The position of the iris can dramatically change the apparent personality of the model and the apparent kind of thought that might be going through the model at the time. So, the position of the iris can be critical to what the photo is attempting to convey.
Travis,
I rarely comment about portraits because I have never taken the time to develop a particular preference of taste for them; I enjoy all styles of portraiture. So, I'll only mention a minor issue that can easily be fixed in the second photo: Notice the curved, grey tonality in the woman's skin tones just above the top of her shirt. At first glance, I thought those grey tones were another layer of clothing.
I like the image and the PP you did to arrive at it. The only bone of contention is that her skin (on my monitor) looks a tad rough. I opened the image in CS6 and selected the skin with NIK Viveza. I then reduced the structure just a bit which seemed to smooth out the skin without losing any detail in her lips or eyes. BTW: it seems as if her lips could have used some balm or lip gloss. I tried selecting them and reducing the structure but it did not look good.