Installing fonts and keeping them organised on a Mac

NWF Installing fonts and organising them 2014-12-01

While I’ve read numerous blog articles over the years on where to find free typefaces, how to use them in different combinations, and what to make with them, I’ve never seen addressed the issue of installing and keeping them organised. All I know about fiddling with digital stuff is what I’ve learned through trial and error, or in a rare instance with the help of a tutorial. Since it’s Monday and tech stuff are on the menu, I might as well walk you through how I make this happen.

The first mistake I made was not to have a strategy

I’m still sorting through my old mess and only recently did I make a decision to stick to my latest system for the foreseeable future. Trust me when I say that a mess can be made even worse, when one jumps from a system to another, since the former didn’t quite work.

The second mistake I made was not to understand the importance of licencing

Since you don’t know what your skills or interests will look like a year or five from now, do yourself a favour and save the original font file with licence. If you don’t understand yet what the differences are, at least save the licence for future reference. Some fonts are free for all sorts of use, whereas others are a total no-go to use apart from in personal projects. There was a time when I thought I’d be more organised when less cluttered, so in quite a genius manner I deleted everything apart from the original font file. There’s a point to the licence that clutters up your computer when you click “Download file”.

The third mistake I made was not to understand different sorts of typefaces

By this I mean that there are various font classifications such as serif, sans serif (sans means “without”), display, novelty, and more. A display font can of course be serif and a novelty font can be suitable for display use, so this part is up to the website to organise, where you download your fonts. My absolute favourite is FontSquirrel, because they keep things neat and lovely to look at as well as quick to navigate. The bonus point is stated in their website header: 100% free for commercial use. Anything you download there can be used in future projects as long as you have the licence (with some exceptions).

So what now?

I didn’t create an organising system based on the font categories used by FontSquirrel from the beginning, but simply saved all of them in single file (haha). Fonts installed on a Mac can be managed in the application Font Book, which you will find in the Applications folder. I’m about to install the font Vidaloka so tag along!

FontSquirrel 1

The device pictures underneath the font name Vidaloka are links, so hover above and click them, and read what you are allowed to do, where you’re allowed to use this font.

The Specimens tab is very useful. According to my newest system I take screenshots like the one below and save them in a samplers folder. In this case, the name of the picture file is “Font – Display – Vidaloka”. Finder will find the file if I look for “font”, it’s useful to know how FontSquirrel categorises it, and the name goes without explanation.

For taking screenshots, I keep the Grab application (Applications > Utilities) in my Dock and have learned the usual keyboard shortcuts, so that the left and right hands are clicking and typing in a fluid motion. While my process presented here might sound laborious, it’s super quick thanks to those shortcuts in different software. Note that Grab saves in tiff format, so you might want/have to change it to jpg or other later. I change it immediately to keep the file size smaller on an old iMac (it adds up when there are colourful images etc. in tiff).

FontSquirrel 2

This sampler gives a great idea of how this font works, whether it is suitable as paragraph or heading font, how it might pair up with another font, and so on. Since I have it saved, I don’t have to go back online just to look at the Specimen. All websites don’t even offer this perk nor can you take the font for a test spin such as in the Test Drive tab. And at some point this font (including licence) may not even be available for download anymore.

Note that some fonts have more than one specimen. Ostrich Sans is an example:

FontSquirrel 4

If the other versions look fairly similar, I grab only one screenshot, but in the case of dingbats there may be more of them. Typically, if there are several specimens, there will also be more than one font file to install.

My next step is to look at the Glyphs overview. Since this is a normal font, I only pay attention to whether it has European letters included or not, because I keep a folder in Font Book called “ÅÄÖ”. It’s a nifty way to check whether I should consider a font when spelling “God Jul och Gott Nytt År” (Merry Christmas and a Happy New Year). (One “ar” is an area unit in the metric system, whereas one “år” is a year; huge difference…)

Had this font been a dingbat, I would take screenshots or print-to-pdf all the “locations” of the various symbols. A weakness of Font Book is that there isn’t a built-in feature to match a letter to a symbol. I’ve spent too much time trying through the keyboard letters, until I had the heureka moment to take screenshots. Have a look at Floralia:

FontSquirrel 3

In the case of dingbats, I name the screenshots the same way as the Specimen screenshot, and add a number at the end to keep them sorted together.

Next you download the font. It will be saved in the Downloads folder as a zip file. Once you have unzipped it, a normal file folder will appear and you can move to trash the zip file.

FontSquirrel 5

On FontSquirrel you will find both otf and ttf files. Both will work fine.

To install the font on your computer, double-click the file and you will see this:

FontSquirrel 6

Click Install Font. This should open the Font Book application, if you haven’t opened it yet.

My Font Book looks like this, with quite a mess still in the collections in the left-hand column but it’s getting more neat by the month (week is too optimistic to say):

FontSquirrel 7

Another weakness of Font Book is that you can’t tag fonts to create smart collections like in iPhoto, but everything is manual. This is the reason for my obsession with keeping track of everything, from naming font sampler and glyph screenshots to creating samplers in a single folder, to keeping original font folders (the ones we just saw in Downloads) sorted according to category. The upside is that it comes with the OS (I have 10.6.8 and it might look different on your Mac) and is free. Font managers are expensive pieces of software.

Here’s a close-up of a portion of my collection column:

FontSquirrel 8

FS is FontSquirrel and refers to their system of categories. IFS is icke-FS (non-FS), fonts from other places such as dafont. FontSquirrel uses tags, too, so a font categorised as Display goes into “FS Display”, and, if tagged serif, will appear in “Stil Serif” (Style Serif). You can see this information below the font specimen.

Some other style collections I have are “Stil Består av bitar” (Style Consists of pieces) in case of for instance Costura, which looks like cross stitch, and “Stil Hög smal” (Style Tall narrow). Think about what you like about fonts, see if there’s a red thread, and create a collection.

My theme (Tema) collections are another example. Fest is Party and Barn is Kids. The rest, I believe, you can figure out. All these topic-based folders  (Style and Theme) will contain fonts found on various websites. For instance in the Valentine collection I have Paper Hearts from dafont. Paper Hearts also appears in “Style Consists of pieces”, quite logically :)

There’s something very useful about Font Book that I actually discovered only recently, namely the Preview menu. The standard view is Sampler, like you saw earlier of the Vidaloka font that we installed. This will show only a portion of the characters and my beloved Å, Ä, and Ö among others aren’t visible.

If you click on Repertoire, however, you will see all the characters that are part of the font file. This can come in handy in the case of webdings also (blog social media buttons, hello – like mine made from scratch). And finally, Custom is a built-in Test Drive! How cool is that.


I mentioned mistakes I’ve made in the beginning and these examples are here to show you that even if you don’t create a huge bunch of empty collection folders yet, at least you might look at fonts differently already when deciding to download or not.

Because the fourth mistake I made was to download aimlessly. It’s a bit like pinning stuff on Pinterest without any aim at all. When boards are a mess, I can’t find my way around them and hence won’t keep track of what you pin, unless a picture appears in my feed. Other users will actually also find you better via search when you name the board “Typography” or similar, rather than “Oh these are so cool”, if it contains font samplers, great movie posters designed, and what not. (Search algorithms may be boring, but they do get the job done as long as you help them.) During the past few months I’ve therefore deleted around 100 fonts so far and more are on their way out still.

I hope this walk-through has shown you how easy it is to start working with fonts. I will write another tutorial in the future about how to create stuff with them, but for now I think there’s enough to chew on.

As usual, if you have any questions at all, please do ask them in the comments and I’ll do my best to help you out. I have no great idea of how fonts work on Windows, so that’s an area you’ll have to ask someone else about, but the functionality in general of this tutorial will work beautifully for Windows users, too.

Are you a Mac user? Have you got more tips and tricks up your sleeve? Or does this post cover something you’ve always thought you will never learn how to do?


2 thoughts on “Installing fonts and keeping them organised on a Mac

  1. Kristy Daum

    I honestly don’t know how many “free” font downloads I have collected over the years; but it is not too too many…so it is probably the perfect time for me to create a system then let it go to bits. Thanks for the FontSquirrel link, it’s always helpful to know where other people have had success.

    1. Nina With Freckles Post author

      Heh, I will never be able to let my system go to bits anymore, not after this over-a-year lasting cleaning up. I can only take it for a short while and then my patience runs out, so it is much easier to just bite the bullet and do the font management properly (alternatively bookmark the font page until one is ready for the big circus).

      I love mixing and matching my fonts when they are well organised, so it is totally worth it! My Christmas cards will be jazzed up in a few days time with the help of my new and functional system.


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