Calligraphy is essentially the art of „beautiful writing“ (this is how the word translates from the Greek), today it comes in many classic or modern variants. Calligraphy is always written with a pen (or a brush) in one gesture, it’s all about the flow of writing, and calligraphers need to attain mastery of their hand and their tools to achieve the effects they want.
Calligraphy is always about the direct expression of the hand. Although it looks lightweight and effortless, it is most of the tine executed very planned and deliberate.
Lettering is closer to illustration, lettering artists draw their letters and then refine them in a number of ways, similar to how an illustrator makes sketches and then creates a finished artwork. Lettering is based on constructing and building the letters, not writing them in one stroke.
It is usually done in pencil and with pens, although you can use a drawing nib & ink, or of course the computer (vector drawing software) or make lettering out of food, objects, embroidery, etc.
Letters can be drawn in a huge variety of styles – serif, sans-serif, blackletter, scripts, or wood type-like decorated styles, and so on. A lot of contemporary lettering work has illustrative aspects or lush swashes combined with top notch letter drawing.
Brush lettering is a bit misleading in its name. I’d essentially put it in the calligraphy category, because though it’s called lettering, you essentially write a script style with the brush or brush pen just like you would in calligraphy. It can be done with simple round brushes or with brush pens.
Type Design is the nerdy cousin of lettering – type designers are basically type engineers with highly technical skills. Type design is what you do when you design a typeface – you build a system of letters that must work in combination, built into a font that you can then use on a computer.
The term typeface means the finished alphabet by itself (almost always drawn on paper first, with either pencil and pen or calligraphy tools), whereas a font is the finished file on your computer, often enhanced by complex programming (Open Type) and always accompanied by technical necessities like spacing, kerning and hinting, which will often go unnoticed by the person using the font. Each letter has to interact with all of the other glyphs in the font, and there are a lot of additional glyphs besides the alphabet like punctuation, diacritics, etc.
These days, there are a lot of handwritten script fonts out there which are a whole science for themselves: you have to know about where to connect the letters to make them look written in one line, and supply alternates to make the font more handwritten – it’s really an attempt at making something that is constricted through technology look as human and organic as possible. There are a few great type designers out there and often their field of expertise spans over the whole range of typographic expression.
What should I learn?
Having done all of the things above, I’d say it’s really up to you and your interests. I myself started out with type design and noticed after a few years that I want to get back to more analogue work and enjoy the materials and the drawing/writing process, so I turned back to calligraphy and lettering.
That said, you can always combine the one with the other. Brush lettering and calligraphy are probably the most approachable because of their proximity to handwriting, and they show instant results.
Lettering can come in a lot of different flavors, and is a lot like drawing and can be combined with illustration. You can also include calligraphic aspects into your lettering, which is what I often like to do in my work. There is definitely a lot you can learn from knowing how a writing instrument affects letterforms, and this will improve your letter drawing considerably.
All of these techniques can be taken over to the computer, and be changed and enhanced. Type design is the most technical of all these arts, if you’re really into building systems and spending a lot of time on the computer making everything fit and perfecting and molding your letters, then this is for you.
I hope you liked this explanation and have gotten a clearer understanding of the similarities and differences of these typographic terms.