I think you should do the best painting your judgment allows. If that means head and shoulders, and the canvas will need to be 20 x16, than that's what they should get. You can dramatize scale with the frame.

But don't paint a giant head, unless giant heads are your signature.

You can desaturate the red with its complement, but I personally wouldn't try to change the color unless I planned to work the whole painting from a grayscale. There's a LOT of reflected color in the face.

p.s. What about some new photos with a white blouse and red scarf?

This is an award and needs to be the same size as the previous one so I'm stuck with the dimensions. And it took over a month to nail her down for this photo session; she's super busy. Between her schedule and the weather (more snow is forecast) I don't think I can grab her again. Also the thing is due the first week of April because they have to get it framed in time for the presentation on April 11th. It doesn't leave me many options. I guess I have to go with what I've got, desaturating the red as much as possible, and hope it works. Thanks for your input.

Leslie,

Another option for knocking back that dominant red shirt, since you can't schedule another photo shoot: paint a shawl over it, or a blazer, in a different color. I'd do thumbnails, check out what different value shawls do for the composition (choose the value according to what gives you the most powerful 3-value composition). Then I'd set up a model or a mannekin in a red shirt with the chosen shawl to see how the fabric drapes.

The red shirt, the red "mud-face" you get in that full-sun light key (the light is not flattering her features in either photo), the deeply-shadowed squint caused by that full-sun light key, and I'll mention the very dominant (distracting) rails here, too -- I see lots of challenges to this reference photo.

Somehow you need to simplify what's going on in this photo.

I personally think that these out of door, in full sun photos, are double tough to make work. I would hate to think that the background that you show is driving this pose.

I think that an indoor shot with controlled lighting (even with the red shirt) gives you a much better opportunity for success.

Is it really all that important to those viewing this portrait to be reminded, with a distant glimpse of water, that she was the mayor of a beach community?

P.S.

What about going to her office and blending in with your camera? Either taking some candid shots or setting up a chair near a window. Maybe she could spare 15 minutes.

Thanks for your suggestions, Mike and Mari.

I was actually hoping for some ideas about how to orient the picture, and which hand treatment and how much of the model to use, but you've all certainly re-sensitized me to the importance of just saying "No" when the subject's wearing something so problematic.

My specialty is "portraits in a natural setting," so that's what people expect when they commission a painting from me. I try to find a background that says something about the individual and that enhances his or her persona. Sure, I could go in and try to catch her in her office but I have no idea what I'd do with those photos; it's just not my style.

With that time line facing me I've been working on it today and I've got the thing blocked in now, using the first pose but cutting her off just at the hem of her shirt to avoid those rails, which bothered me, too, and then using the head I posted. I ended up with a horizontal orientation because it worked better for getting both hands in without making her too small. I'm going to soften those harsh shadows in her face and also dull the red, leaving only the highlights of the shirt bright and bringing in red in her ears and lips and so forth. And I'll show you what it ends up looking like and you can all say, "I told you so!";) But nonetheless I think she'll like it because it's what she wanted.

Oh, the portrait's going to be presented at the annual NJ Conference of Mayors gala and it will hang in her living room in Stone Harbor, right by the beach.

I am reminded of this great painting by John de la Vega ...

http://www.portraitartist.com/delavega/lisarail.htm

I'm not suggesting that you hoist this woman's leg up onto the rail but maybe some ideas on what to do to make the background more interesting.

Please rethink this approach. For starters, by going to her office and photographing her next to a window, you'd probably get much better shots of her face and figure without the squinty eyes, harsh lighting, messy hair and the gigantic red inflated shirt. Then go and compose a beautiful photo of your/her favorite natural setting and combine the photos...i.e., paint it into the background.

The great outdoor backgrounds of the Old Masters were done separately...the model posed in the studio where the light was controlled. The background was painted in separately to create a mood and enhance the figure.

Here is a painting that Sir Thomas Lawrence did and he did NOT paint or have the model pose outdoors.

And here is another one NOT posed outdoors. I would like to think that no matter what your "style" is - it will not get in the way of producing the highest quality painting that you can muster. Poor reference material is a bad way to begin - most especially when you have a choice in the matter.