Classic Portrait Oil Painting

12×16 Oil Painting on Gessoed Board

Above – Final Painting

This is my largest painting to date. Sometimes I play. Playing has value. Sometimes I am very serious and want to get it right. What is right?  I wanted  to create a classic painting, with accurate skin tones for this person – I wanted to reflect accurate hues, tones and chroma appropriately sculpting the form of her face – within the lighting in which she was photographed.  “Accurate” is a tall order here – starting with the fact she was photographed in weird light, the photo was printed – meaning a different shift in colorspace. So many things,  have interfered with accurate. That being said, I was deliberate and wanted to do my best.

I took the reference photo while in New York at a gallery opening a few years ago. She was very willing to pose, as I find is usually the case in New York City.   Her dress was black dripping with multiple chains. She had one bare shoulder.  The bare shoulder was covered with huge tattoos likewise all down her arm. She had a long ponytail. Her eyes were rimmed in bright red make up.  I think she might have been disappointed had I not ask to photograph her.  I thought she might be enjoyable to paint.

 Initially, I spent an hour mixing paint. Based on colors and values in the photo, I created a  large variety of subtle shades and hues for her face. That become an enjoyable part of painting – believe it or not – it’s own meditation.

Below is mid stage of the painting. It was a modern, rather vixen look  – but that’s not what I had in mind.

Above – Portrait Stage One

I wanted a more classic look.  I thought a vintage hairdo might be interesting and added a bun to the back side of her head and a long curl.

 After looking at the painting for a while – nearly an hour later I decided  to remove the back bun and curl I added – to wipe off the paint from that vintage variation. The  hair paint was still soft/wet.  I then only slightly modified her original “do”, softened and blended  the edges of the hair where it met the face and its exterior edges. In the final image above, I also subdued the red rimmed eyes, subdued the eyelashes, and softened the lip lines. Some of the boldness of the image was lost, but I was after softer and more subdued  look – shocking!! Perhaps, I should have and could have been more careful in painting her neck and upper chest.  I did not do so intentionally – not sure it was the right decision.

Hint:  We all need time away from out art periodically, to bring fresh eyes to our work. There are many ways painters do this.  Viewing your artwork in the mirror can help as well. What I do most often is to photograph my painting with my phone periodically –  a series stages of the painting along with the latest stage.  I can view these images anytime – and I do so frequently. Viewing these images small  on my phone gives me distance and a different way of looking at the painting.  I find this process very helpful and I do this with every painting. It shows me things I might never have seen when looking at the larger painting.


I  also wasn’t sure what I would do for attire. I could leave her shoulders bare – or dress her in some way. Again, I photographed the painting with my iPhone and opened it in Painter to explore some alternatives. Thats how I tested a few strokes of “fabric on her shoulder”.  (Bye the way, I also used Painter to test adding the bun which I removed.) I decided that whatever I creates as attire would be loose and easy, hence, I returned to my paints.  In the end, I used the palette knife to create her “stunning” dress top. That was fun!!

Over all I learned a lot in the painting process – always the case.    Once again I learned to try to get color, values, and brushstrokes right the FIRST TIME.  “FIXING”, especially skin, doesn’t usually lead to good results.

Related Images:

Portrait Painting of Girl

Portrait of a Girl – 9×12 Oil on Gessoed Board 

I think portraits are the most challenging images to paint – even using a reference photo.  As you can see below, I create a very loose sketch initially and then work into the detail. I also always want to bring some level of artistic expression and creativity to the painting rather that to just to paint what I see. This can be challenging to envision, and a bit frightening to execute. I have to let go and take chances.  I consider it better to try and screw up than to play it safe.

Below – Loose Tonal Value Portrait Sketch

Below – Starting to Add Color

I  always like this stage of a painting.

“Oh Give Me A Home”

“Oh Give Me A Home” 9×12 Oil on Gessoed Board

For years there was a herd of Buffalo on Beaver Valley Road in Chimacum WA, a town not far from me. What a sight it was. It was the only herd of Buffalo I’ve ever seen. 

During a drive by one spring day, years ago, there were quite a few calves. I’ve always loved the photos I captured, one of which inspired this painting. I don’t think the buffalo are there anymore – not sure.

Below is my initial sketch on a gessoed board I toned.


Vessel Loading – Bainbridge Island to Seattle

I spent the day with a young friend from Seattle on her13th birthday more than a year ago. Now it was time for her to return home.  I took her to the ferry – her mom would meet her on the other side. Amongst others, I took this photo as she prepared to board the Bainbridge Island Ferry.

A few days ago,as I perused my photos searching for any interesting reference photo to paint – I came upon that image and was inspired to paint it. Getting the perspective right was challenging  for sure and the was a dominant consideration for this painting. 

Initial Sketch and Design 

Developing Values and Perspective

Values and perspective  and image content are increasingly developed. 


I’ve  been reminded of a digital painting I created a few years ago. I was in New York and walked down the stairs into Penn Station. Immediately, I saw this little girl playing the trombone and her brother holding the music.  I love the story and the memory. I added a few dollars to the trombone case.

Related Images:

Suspending Judgement

Suspending Judgement –  8×10 Oil on Canvas

We’re so hard on ourselves, always wanting to get it right, the design, the color, the brushstroke, the values. perhaps you’ll wonder if others will like it.  What if we suspend  this brainwork and jump into bonafide play – just throw some paint around. No one else needs to see it. Tell the brain to take a rest – you won’t be listening – and you’re doing it just for your self!!  Digital or traditional painter – it won’t matter. That’s what I did to create this painting.

It was fun. There was no thinking – no right or wrong.  I wanted “to do” and not “to think” about it. Lets face it, some of what’s been learned always shows up a bit anyway. You cannot teach yourself “not to walk”  – you just do it. Your painting should take not more than 5 to ten minutes. Try to paint quickly so you don’t have time to think.

For this painting, I only used the left over, already mixed oils on my palette, limiting my  color choices and I started “plopping” on paint with a palette knife. Who knew where it would go – there was no plan. Remember, NO THINKING – just play! We all need to play. It’s amazing the part of yourself you might discover. I had no idea there would be polkadots all over. Never did I DECIDE, “I will put dots all over”. I put a few on the upper part of the painting with the end of a brush, then a few more and a few more. I did think it was pretty cute however.

Funny, I usually do my wildest painting  experiments using a pear as subject.  I don’t have to think about creating a pear shape.  You might want to create something different.  I had a student say she didn’t want to paint a pear but she would paint and apple. Okay, apples are cool and anything else!!

Since you’re here and we’re looking at pears. I’m going to show you another painting. Below is the second oil painting I ever did.  I thought it was ok – for learning to use oils. 

Now, 6 weeks later, I decided to paint from the  same reference photo again – it’s simple, fast and just practice. This time I did a value sketch – I don’t think I did that for the first painting and it’s vitally important. Then, I added paint to it. There’s a big change from my initial painting.  I thought you would enjoy seeing the change.

Orange and Pear Simple Still Life

I’m sure I will paint the reference photo again in a few weeks ti see if I can’t take it in yet another direction. Thank you for taking a look. Winifred








I’m painting far more than I anticipated and hence posting more blogs. If there are too many – do let me know.  You  can also unsubscribe but I would hate to loose you. Winifred

Related Images:

Dirty Birds – Oil Painting

Dirty Birds – 12×9 oil on gessoed board.

Dirty Birds by Winifred

  There is always a challenge in painting. There were so many decisions with respect to design, values, color and chroma. I still see changes I will likely make. There were many elements in the photo reference which I ultimately eliminated for design and simplicity sake.  The photo which inspired this painting was taken in Guatemala by photographers Daphne and Art Carlye who often work summers with Rotary International.  There were lovely palm trees in the background which ultimately I ignored.

Below – initial tonal sketch 

Below – INITIAL PAINTING – Too much detail – No place to focus. No place to rest ones eyes – though there are some aspects of this image I like. In my initial painting I found my eyes darting all over the place – not a good sign.  Everything is foreground and everything was the same levels of saturation and contrast. I know better than to do that. I scraped the paint off the background and made changes to design and expression.  

Below: This version is not too bad and I rather like it but I decided to push the background  back even more by simplifying  it –  and muting the colors, thus arriving at the final version at the top of the page. I may have made a mistake in that regard – but, I share my mistakes with you as well.  

What do you think? Which image do you prefer and why?