Painting Bridges, Alleys, and Avenues of My Favorite Cities

I was born and raised in the suburbs, with rural farmland and city centers nearby so I have an unbiased appreciation for both. I’m attuned to the natural elements around me and I love to be outdoors, but I also get so energized by the sights and sounds of the cities I visit or live in. And cityscape painting or sketching urban spots has certainly helped me hone my perspective drawing skills because with so many visual elements to contend with, I have to be able to create a sense of space in which objects look like they share the same environment relative to one another.

Although one-point perspective is easy to grasp, I’m still working on using more complex layouts of linear perspective. In the meantime, I have a few workarounds that I use to keep myself in a perspective mindset but don’t necessarily require me to work out all the details.

Cropping: One thing that I don’t think artists use enough is creative cropping when it comes to settling on a composition for a cityscape painting. For instance, if I taper my composition in at the middle, an illusion of distance is created. Artists often do this in cityscapes where the buildings and roadways, for instance, veer together at one point in the distance.

Via Pietro Micca by Valerio D'Ospina, 2010, oil on canvas, 57 x 51.
Via Pietro Micca by Valerio D’Ospina, 2010, oil on canvas, 57 x 51.


Color: Over the span of a day, light on a form—a building façade, let’s say—changes consistently, though sometimes subtly, as the hours tick by. None of us usually have the time to watch that play of color change minute by minute, but I always try to remind myself of how subtle color changes can really make an impact. When trying to go from near to far in a cityscape painting, I don’t need to drastically alter my colors; minute changes—more like tinting—will give me the effect I want.

North Window in Afternoon by Bennett Vadnais, 2010, acrylic painting on paper, 12 x 16.
North Window in Afternoon by Bennett Vadnais, 2010,
acrylic painting on paper, 12 x 16.

What looks right: For me, it all comes down to what looks believable rather than whether or not it falls within the mathematical boundaries of a more complex perspective drawing. So I stop looking at my subject and just evaluate my drawing or painting. Does it look believable or does my eye snag on something not quite right? That assessment is my highest standard and one I keep in mind no matter what I work on.

Scrub Free Vessel by Christopher St. Leger, 2008, watercolor painting, 26 x 38.
Scrub Free Vessel by Christopher St. Leger, 2008, watercolor painting, 26 x 38.

But that isn’t to say that I am not always taking steps to sharpen my city smarts–those drawing and painting abilities that allow me to evaluate quicker and work on more complex compositions. Using these skills well means the difference between having to use a lot of creative workarounds and working exactly the way I want when I paint cityscapes.

The lessons combined in the About Town Drawing & Painting Collection are ones that we can easily incorporate into our art practices–and there is plenty of visual inspiration from practicing artists included as well. Seeing how talented artists break down their painting practices and also give us tips on how to conquer architecture, cityscapes, and urban sketching makes this collection an incredible value. I am ready to make the most of this upcoming summer with my eyes searching all around me for my next “downtown” composition, even if that turns out to be simply looking down the street from the house where I live! Be sure to order this collection for yourself, and as always, enjoy!

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Courtney Jordan

About Courtney Jordan

  Courtney is the editor of Artist Daily. For her, art is one of life’s essentials and a career mainstay. She’s pursued academic studies of the Old Masters of Spain and Italy as well as museum curatorial experience, writing and reporting on arts and culture as a magazine staffer, and acquiring and editing architecture and cultural history books. She hopes to recommit herself to more studio time, too, working in mixed media.   

3 thoughts on “Painting Bridges, Alleys, and Avenues of My Favorite Cities

  1. Some beautiful work shown here. If you get a chance, check out Stephen Magsig’s work too. He’s a plein air painter who does gritty paintings around Detroit. Very stark and thought provoking in these tough economic times.

  2. Courtney—

    I love all of this work. This is an excellent commentary on one of my favorite subjects.

    You are so right. Your eye is the best judgement tool you have. You can be mechanically correct when using the principles of perspective but be off visually.