Dante' Photo
 

This casual photo shoot developed into a commission for an out-of-town client.

The expression and hands are key, though the cropping is too tight, in my estimation. The following photo shows more air around the subject and may serve the design.

My plan is to go with a dark, plain backgound.

Any comments?

More Air
 

Here is the photo showing the composition I believe will work, though the expression above has been selected.

My response.
 

Personally, I prefer the expression on the photo below. It is more dynamic.

How far "out of town" is the client? The reason I ask is that I would consider reshooting this subject.

Here are some of the problems I see with this set up: The shirt is too big, especially the sleeve length. All that stiff white fabric makes busy distracting shadows everywhere.

I'm confused as to what the rolled up fabric on the chair is. Is it a pillow?

The skintones in the example are very hot pink. I assume you would correct for that in Photoshop before painting from it though.

There's a risk of it being a portrait of a white shirt, if you go with a dark background. Perhaps a midtone background would help, but the shirt is still a very big part of the composition and has all those distracting shadow shapes I mentioned above.

Also, neither expression looks relaxed and natural to me.

The things I like about it are the strong diagonal in the composition overall, the good shadow contrast ratio and shadow shapes on the face.

Sorry to be such a downer on this and I hope you can reshoot to get some more photos.

Dante's Progress
 

Here is where I am up to with this. Initial lay-in of color has been done. (Shadow on top is from the easel.)

I will go back in to evaluate shirt, add more modeling and temperature changes in skin tones, accents and highlights, finish hands.

Your comments are appreciated.

Sail Boat
 

My husband suggested the addition of a toy under his arm, such as a football. I played around with a few items and like this sailboat.

However, the simplicity of the composition as is - especially since I cannot get the model back - is winning my favor. Would you agree?

I'm glad you simplified the setting. To be honest, there was too much girlie stuff for a boy's portrait.

In my opinion, you can't go wrong putting a sailboat in a portrait. But then, I love to sail.

The Boat's In!
 

Dear Jeff:

I'm so glad you said that! We're sailors also. Here it is with boat.

Now I can finish the painting with all these pieces in place.

The Shirt is Excellent.
 

The photograph of the shirt is wonderful. It enables you to really do some dramatic folds. I, personally, would redo the cuffs so that the boy is attired properly. The boy does not seem to be the kind of child who would wear his clothes in a dishevelled manner. If you paint him that way, it might appear that he is too posed.

The photo of the face is also wonderful as it shades the face in such a way that emphasizes the expression and highlights the eyes.

I really like the fact that you are redoing the background. It is too "busy" for my personal tastes.

Overall, I think that the painting will look wonderful and I anticipate your completion of it.