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The truth is, you have everything you need to start this pastime today. At it's essence, all you really need is something to write with, and something to write on. Certainly there are all kinds of pens, papers, and accessories to make this more fun, but if you have a pen or a pencil, and something to write on, you are already prepared.
That said, I'll describe the attributes of some of the basic supplies so you understand their benefits and limitations.
Pens and Pencils
Pencils are a good way to start, they give you the opportunity to erase if you find you've done something you don't like. Pencils give you the chance to create variations in line thickness and depth by manipulating the sharpness and angle of the graphite on paper. You can make very fine reference lines or very bold outlines. And you can erase your mistakes.
You can use pencils for roughing in your work, and then working over your layout lines later with pen. Or you can use pencil throughout.
Note: if you are going to block in your sketch with pencil to later over-sketch with pen, be careful not to add too much detail. The fine detail should be reserved for pen, and should be done LOOKING at the scene and not just coloring over pencil lines.
Pencils though do tend to smear, and over the course of a sketching session it is inevitable that you will rub previous pencil marks with the palm of your hand or sleeve. And closing your sketchbook over your pencil drawing might cause the marks to smear as well.
Note: A thin layer of watercolor over your pencil marks will “lock” them in and make them more permanent. A very thin yellow ochre (or similar) seems to do a very good job of this.
Pens are more permanent. That is good and bad. Good, once you are confident in your mark making, bad when you make a mark where you don't really want it. Most sketchers are fine with that. There are lots of different pens to choose from. Great art has been created with a good old fashioned Bic pen. Most standard pens use ink that is NOT waterproof, so if you end up doing a watercolor wash over your sketch the ink can smear pretty dramatically.
Note: Some sketchers use this to their advantage, and incorporate the bleeding ink into their sketch design. It can create some very interesting interpretations of the scene you are sketching.
Types of Pens
Standard Ball Point -best for sketches that will not be painted over
Fine Liners – Like Staedler or Micron, available in a variety of tip types and thickness, and normally with waterproof ink
Fountain Pens – There is just something fun about writing and sketching with a fountain pen. You can buy ink cartridges, or fill using a converter with bottled ink.
Fude Pens – A fountain pen with a bent nib; this allows you to make a variety of line thicknesses and expression using a single instrument.
Erasers
If you are going to use pencil you might want an eraser. I'd recommend a kneaded eraser, which is less harmful to most specialty papers and allows you to mold to a configuration that is more shaped to the lines you are trying to erase.
Types of paper
There are all different kinds of paper. What matters to sketchers is thickness, color, and surface.
Thickness matters because a thin paper may bleed through when using a strong pen or wet media (watercolor, marker, etc.). Thin papers are also prone to buckling when wet. It is very difficult to avoid buckling when sketching and painting on location, but thicker paper minimizes that.
Color is really personal preference, papers is available in all shades of white, toned tan, or many other colors. I like white paper because it suits everything I want to paint, but I've seen some pretty interesting sketches on colored paper. Typical thickness of paper are 90 and 140 lb, both pretty good for water media.
Depending on what you are using for sketching, paper can be smooth or rough. Cold press paper has a rougher surface (called “tooth”), and is great for water-colorists. But if you are using a very fine pen (Micron .005 for example) it can eat pen tips, and it can be difficult to sketch exacting detail. Hot press paper is quite smooth, and good for sketching and detail with even the finest pens. But watercolor reacts quite differently to hot press papers. Not necessarily in a bad way, but if you've painted on both you will quickly see that paint is a little less controllable on hot press papers.
Types of sketchbook
You don't absolutely need a sketchbook, any more than you need a special paper to get started. I've seen phenomenal art on the back of envelopes, on old pieces of sheet music, or on restaurant menus. But a sketchbook is a great place to keep a history of your work. There are so many options to choose from, including all the various paper types I've mentioned above. I'd recommend to start small. I have little 5 1/2” x 4” I like for small sketches, but my go to for Urban Sketching is a 5” x 8”. These can be purchased in either Landscape or Portrait orientation.
These books can have either be spiral bound, or book bound. I like the book bound because I often sketch across pages. So for a 5 1/2” x 4” sketchbook I get a painting area of 11” x 4” (landscape) or 5 1/2” x 8” (portrait). But everyone has their own preference. The only thing you can do is try. A sketchbook can take quite a while to fill, so if you can afford it, don't go cheap. Etcher makes a nice book, as does Moleskin and others. Pay attention to the paper type, a nice looking sketchbook with the wrong paper will not be fun.
Fine Liner Pens
There are some relatively inexpensive artist pens available, my favorites are Micron and Faber Castell. These are available in a variety of line thickness, all the way from 005 (very thin) to brush pens (like a paintbrush pre-loaded with ink). Some folks like very fine lines and some folks like rich expressive lines, you'll probably want to try a variety. One thing to note, the thinner the line is, the more fragile the tip is. When I use a 005 Micron on cold press (rough) watercolor paper, I ruin the tip long before I run out of ink. Especially with the finer pens, you need to be careful about the angle of the tip on the paper, and the pressure you exert on the tip.
Fountain Pens
Fountain pens are available as dip pens, with ink cartridges, or with converters so you can fill the pen with your own ink. It is sometimes difficult to find pre-loaded cartridges with waterproof ink, so my choice is a fountain pen with a converter that I can fill with my own waterproof ink.
A FUDE fountain pen is a bent nib pen, and the bend nib allows you create a variety of expressive line widths from a single pen.
Fountain pens can be a bit fussy. They can dry out if not used frequently, or they can clog up if you are using them on rough or cheap paper. For me, it is worth the frustration. I love the feel of a fountain pen, both for writing and for sketching.
Ink
If you are using a fountain pen and choose to go the converter route, or choose to simply use a dip pen, you would need to have ink. There are a lot of inks out there, in different colors and darkness. I use Noodlers Ink, it seems to flow pretty good in the pen, and the black I purchase is a nice rich black. But color and intensity is a personal choice, and might take some experimenting to find one you like.
Note: With any pen or ink, if you are intending to put a watercolor wash over the ink sketch (and do not want the ink to bleed), make sure the ink is waterproof.
Watercolors
There is nothing that says you must use watercolor, or any specific medium for Urban Sketching. You can use whatever you want. But watercolor tends to be the most common choice. It is portable, you can bring it in your carry on bag (pans, not tubes) even on a plane, it is not terribly messy, and it is inexpensive. You can spend a ton of money or artist grade watercolor paints, but if you are just starting out I'd recommend buying an inexpensive set of paints that give you a wide variety of color to choose from. A good sketch with a thought out composition and cheap watercolors will look much nice than a poor sketch with expensive paints. Once you get a feel for what you like, you can explore the many options available.
A watercolor paint set should have a decent mixing area in the cover. If it doesn't, a small plate (white) works just fine.
Brushes and water
If you are going to use watercolor as your was, you will need a couple of brushes and some water. A 12 round and a 6 round are more than enough to get started. I bring a water bottle with me, and put it in a cheap disposable plastic cup.
A nice portable solution is a water brush. A water brush has a reservoir of water in the barrel. You squeeze the barrel and that soaks the bristles. It is a little harder to control the water flow than a cup full of water, but if you are just splashing some paint on a sketch they work quite well once you get used to it. They are cheap, and I always have a few in my kit.
Markers
Colored (or simply gray) markers are an easy alternative to adding highlights to you sketches.
Binder Clips
I always keep 3 or 4 with me. They are a good way to hold my sketchbook pages down on their edges, and holding my sketchbook to a board. I use magnetic binder clips to attach my (metal) pallet to my sketch board.
Other stuff
Extras – Pens, pencils, etc. You will lose something, or you pen will run out of ink halfway through a sketch. Be prepared.
Sketch-board – I just use a small clip board and remove the spring clip. If I am using single sheets of paper I can tape them down with masking tape, or if I am using a sketchbook I can use binder clips to secure the sketchbook so I have a solid surface to sketch on.
Paper towels – Essential if you are using water media (or have to clean up after filling your fountain pen with ink).
Masking tape – Good for taping loose pages to your sketch board, or anything else you need to hold in place.
Straight edge – A straight edge might be helpful if you are trying to be precise with your perspective, or simply struggle with a straight line. I use one occasionally for pencil layouts on complex scenes. But when I start to draw detail over them in pen I like the expressive nature of hand drawn (imperfect) lines.
Folding chair – I bring a small folding stool to sit on when I sketch. I don't like sitting on the ground, and this helps me set up anywhere I want to sit.
Color wheel – I bring a small color wheel with me. It helps me find and verify that the color combinations I am choosing will work.
To me Urban Sketching is about the line. When I am painting more realistic watercolor paintings the pencil lines disappear under the layers of paint. With Urban Sketching, I think the pencil line is an expressive part of the scene, and I don't want to lose it. This is why a lot of Urban Sketchers work in pen. Even if they use paint, it cannot normally cover the line. Even with pencil sketches, the light watercolor washes that are typical of this type of art still shows through. Many sketchers do not use any paint or color at all.
Different types of strokes can add depth, texture, and value to your sketch. It is beneficial to be able to execute varieties of line work to get the most out of your sketch.
Long Hatching
Short Hatching
Cross Hatching
Curved Hatching
Scribbling
Stippling
Weaving
Uneven Hatching
Design
All these various strokes can also manipulated to increase shadow and value to your sketch. Varying the line spacing, varying the line weight, and good use of directional or cross hatching can add depth and realism to your work.
Light also adds depth and interest to a sketch. Paying attention to the direction of light and shadows creates value, establishes three dimensional shapes, and adds interest to your art.
Skills to practice
Being able to segregate and identify values in a scene
Creating consistency in your line work, start loose end loose, start tight end tight
Line work also allows the sketcher to either draw or imply texture. Depending on the result you are working towards, you may choose to fill a wall with bricks or a roof with shingles, or may use a few scattered bits of brick and shingle to “imply” the texture of the entire surface. In most cases when properly executed, the viewer will fill in the blanks.
Practice sketching subjects
Bricks
Paving Stones
Shingles
Roofing
Siding
Keep strokes consistent but with some variety
Let line direction define the textures contour
Remember texture changes with contour and perspective
Remember texture follows light and shadow
Rather than fill it all in, suggest texture (let the viewer finish the drawing)
Tips
Slow Down
Trust your eyes, not your brain
Determine where the light is
Vary your pencil / pen grip to change the look of your drawing
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