Outlining is a smart way to take ideas from the scrambled mess that is your brain and arrange them for clarity and purpose. And yes, “there’s an app for that.”
Note-taking apps Evernote and Simplenote are popular as outliners. Scrivener, an application that’s a hit with writers of all stripes, comes with an outlining feature. OS X’s native apps Reminders and Notes also make great outliners — but these are not your only options.
There are some decent standalone outliners, both for the Web and for your desktop. You can use them for taking notes, capturing ideas, planning a trip — for pretty much anything that will benefit from an organized, hierarchical approach.
For Mac users, there’s a nice, but limited selection of outliner apps. Here’s our list of the top three. Take your pick!
Tree ($9.99, 14-day free trial)
Ideal if: You want an outliner app that’s powerful but doesn’t overwhelm you with all that it can do
True to its name, Tree takes a tree-like approach to outline hierarchy (as shown in the image below). This horizontal arrangement looks and feels more intuitive than the usual list-like vertical one. But if you do prefer a list view over the tree view to see expanded outlines, that’s not a problem. There’s a toolbar button that allows you to switch views.
The tabbed interface means you can have several outlines going at once. You can also use Rich text, add notes and checkboxes, and export outlines as .OPML documents. The labeling feature allows for better organization, although it could do with a bit of highlighting. As of now, labels appear as tiny, colored arrows and dots that are hard to see.
Overall, Tree makes for a fuss-free experience. Check out the following unofficial intro video above to see what the app is capable of. The video is a couple of years old, but it’s still relevant.
OutlineEdit ($8.99, free trial)
Ideal if: You like lean and uncluttered apps that don’t try to be everything for everyone
OutlineEdit is my personal favourite in this list. If distraction-free apps are your thing, you’ll love OutlineEdit. Its feature set stays out of your way and allows your ideas and words to take center stage.
You can create, structure, and rearrange your outlines with ease. You can tag items with colorful labels, add side notes, search through your outlines, and send them to Evernote and Kindle. There are a handful of options to customize window behavior: you can dock the app window, keep it floating over other apps, or even make it appear translucent.
The app makes suitable use of the Mac’s versioning control under File > Revert To for accessing past versions of your outlines. Safari users might want to get Marker, a free companion app for OutlineEdit. It allows you to highlight text snippets on the Web and bring them into a new OutlineEdit document on the fly.
“I’m a pretty big fan of outliners and have been for a very long time. I personally use and love OmniOutliner Pro but not everyone needs that kind of firepower. This looks like a nice simpler alternative.”
Patrick Rhone, OutlineEdit on Minimal Mac
Scribe ($12.99) is another minimalist outliner worth checking out.
OmniOutliner (from $49.99, 14-day free trial)
Ideal if: You’re looking for a versatile solution that can handle EVERYTHING from your monthly budget to the novel you’re planning
When compared with other outliners, OmniOutliner looks complex, and to some extent it is. But its workflow is not all that difficult to grasp.
What stands out as a particularly useful feature is the set of outline templates you get to work with. The templates give you a relevant readymade structure for your outline. You just have to focus on replacing the placeholder data with your own. Choose from styles like Budget, Class Notes, Book Draft, Checklist, and Journal. See how time-saving that could be?
Apart from the usual tasks like item creation, indenting, and reorganization, there’s more you can do. Enhance your outlines with notes, dates, highlights, and audio recordings. Customise the toolbar and keyboard shortcuts to speed things up. You can even use custom styles to change the look and feel of the interface elements down to the tiniest detail. And you can experiment with quite a few hidden features (like the ability to export files as .PPTX) that make up this sturdy app.
The bottom line is that if you want an app that takes a minimalist approach to outlining, OmniOutliner is not it.
It's an @omnioutliner kind of morning. How I love that app. Freedom to think and plan in a way that feels natural to me.
— Matt Gemmell (@mattgemmell) July 6, 2015
OmniOutliner has an iOS version ($29.99) as well. If you want an outliner that’s powerful but not as pricey as OmniOutliner is, give NeO a shot. It’s costs $6.99 and comes with a (limited) free trial.
Apps That Didn’t Make the Cut
Some good outliners have either fallen by the wayside or are getting there. Maybe their developers have moved on to other interesting projects. Maybe there’s not much of a demand for a desktop outliner thanks to nice Web-based outliners as well as all-in-one writing apps like Ulysses and Scrivener. We don’t know.
Here are a couple of popular outliners that didn’t make it to our list because they’re not up to date. Keep an eye out for them, just in case they make a comeback or see releases on mobile platforms.
Outlinely is a minimalist text editor and outliner rolled into one. It comes with a 14-day free trial. The default outline that pops up when you open Outlinely for the first time walks you through the main features of the app.
@outlinely I'm enjoying Outlinely. Any chances of an iOS version?
— Steen Christiansen (@dissemination) October 28, 2014
Cloud Outliner ($9.99)
We have covered Cloud Outliner before. It’s a simple app that promises to keep your outlines in sync across your Mac, iPhone, and your Evernote account. The iOS version ($6.49) is still going strong, but the Mac version hasn’t seen an update in more than a year.
Do You Use Outliners?
Think of outlining as text-only mind mapping or solving jigsaw puzzles using fragments of your thoughts. It puts your ideas in a digestible format and gives you a roadmap of sorts to start taking action. If you want to get your thoughts in order, an outliner is a good place to start.
Are there any other interesting outliner apps we should know about?