Here's how I did my calligraphy for my outer envelopes. I did a really simplified approach with only 3 base lines instead of counting nibs to determine correct height, etc. It took me about 3 hours to do 40 envelopes.
Materials
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Speedwell's C-5 (the narrowest nib for Italics)
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Higgins waterproof ink
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Smooth Cardboard (like from a new shirt)
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Ruler
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Marker (bold--I used a bright blue Sharpie)
Steps
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Print out all addresses in a font similar to your calligraphy style. Pick a font size that allows the longest address to fit on the envelope. (I used Apple Chancery for my font).
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Find the longest address and paste it to a cardboard guide. Draw room for stamp so you know which end is "up".
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Draw base lines under the addresses so they are visible through the envelope so you don't have to put pencil lines on the envelope itself. Put the guide in each envelope to be addressed.
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Start calligraphy. I could not see the letters through the envelope so I used the cardboard guide for the approximate size of the letters but referred to my print-out (step 1) so I would know when ascenders or descenders were coming. This way, I could avoid a mess when a descender (ie, g or y) aligns with an ascender (ie, l, k) from the line below it).
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Space envelopes out when they dry so ink is not smeared.
Tips
1. Use a fine point nib--C-5 is the thinnest I could find. When the nib is too thick, the calligraphy looks heavy & black like Old English rather than light & elegant.
2. Expensive paper sucks up ink like a paper towel. I was dipping the nib into the inkwell, and it was hard to avoid "blobs" where the paper absorbed extra ink. Consider a felt-tip pen if you have this problem.
3. Paper with a lot of cotton fibers also can be "pulled" by a metal nib. Consider a felt-tip pen if you have this problem. NOTE: A C-4 nib was easier to use because it did not "blob" as much as a C-5 or pull the cotton fibers. If you don't mind the heavier look of a thicker line, you may want to use a C-4 instead.



