As I'll be teaching a workshop in the Sierra Buttes in a few weeks, I wanted to do a post talking about my setup, present and past, to take any mystery out of it, as well as help inform those that are contemplating the purchase of an umbrella, a pastel box, backpack, etc. The photos above shows the way I'm currently working. I'm using an allinone easel, mounted on an old Manfrotto tripod. I can adjust it to comfortably work sitting or standing. This is a 10 x 14 pochade box, which has a hinged foam core panel to mount your paper on. There is storage behind the easel, which is held by velcro. I made a simple storage pad out of glassine, canson, and cardboard, to hold blank paper, as well as finished art, which fits in that space. I can also use the pad to mount paper on for a vertical composition, as shown in the top image. As far as umbrellas go, I've used a variety of them over the years, losing several every year to unexpected gusts of wind. I am currently using the bestbrella, which has worked well for me for the last 7 months. One improvement over other umbrellas is that it is silver on the outside, and opaque black on the inside, reflecting heat, and eliminating diffuse glare. A white umbrella can over illuminate your work under certain circumstances. The mount is extremely sturdy and adjustable.
Everything fits into the backpack below, plus a bag for the tripod, and the umbrella mount. If I want to, I can secure the tripod bag to the backpack to keep my hands free. To choose a backpack, I simply went to a sporting goods store with all my art supplies, and started trying to fit everything into the packs they had on display. The folding camp stool is from there as well. Other items I carry are a camera, usually looped through my belt, water, sketchbook, and and wipes for my hands. It's ok to have extra room for snacks, extra clothes (windbreaker, hat).
Here's a typical setup by the side of the road. No umbrella needed, as it was an overcast day.
The above image shows the way I worked for about 10 years. Same stool, backpack, and tripod as I currently use, but a large, wooden pastel box from Dakota Art Supplies. Also shown is one of the many umbrellas that took a beating over the years.
Below is me finishing one last piece before hiking out on the last day of a packtrip in the Sierra. Note the white umbrella. The dark one's provide a more balanced shade than the white umbrellas, imho.
Here's an 'ultralite plein air' setup: One small box of pastels, many of them cut in half to accommodate more colors, a tracing pad cut down for storage, with a same size sheet of foam core to clip paper to. The whole thing fits in a zip-lock bag. Just sit on the ground and start painting. I took this setup backpacking last year, and had a similar setup for a raft trip down the Grand Canyon a few years ago.
The truth is the gear is of less important than the experience. At the same time, you want equipment that will be comfortable, reliable, and easy to use. Being able to stand, or sit, as well as control your shade, are very useful 'tools' for working outdoors.
You have more options about where to paint that way. Lastly, consider the weight of everything. An 'ideal' setup is the one you're willing to carry with you for a couple of miles.