Top 5 Retro Typewriters for Writers Who Want to Type Like Their Heroes

A typewriter was the tool of many of the greatest writers you've read your whole life. You can get a little closer to them with your writing by getting your own typewriter, whether it's a restored classic or a modern e-ink device.
Averil Gleason
Updated January 28, 2022

Tom Sawyer. The Wicked Witch of the East. Stella Kowalski (Stellllaaaaaaa!). All these characters, and so many more, were born on the pages written with a typewriter. Literary geniuses like Mark Twain, L. Frank Baum, and Tennessee Williams, among many others, used typewriters like their lives depended on it. They helped produce portals to other worlds. They were catalysts in creating some of the best pieces of fiction this world has ever known. So, like, wouldn’t you want to do that too? For this Dealspotr Top 5, we’re taking a look at the past so you can focus on your future. Let’s take a closer look at the best typewriters on the market that’ll bring you a little closer to your long-gone literary heroes.

Be Free, Writer

retro typewriters writers

Freewrite, $599

The fact of the matter is you can’t go wrong with a typewriter (see what we did there?). The Freewrite typewriter blends the past and the present to create an easy way to write without the distractions that come with the computer, or the aches that come with handwriting your stories. The Freewrite typewriter has a digital e-ink display and holds more than 1 million pages worth of drafts on its storage device. And these drafts? They can be seamlessly transferred from your Freewrite to the cloud with the device’s built-in WiFi. Write for 30 minutes a day for up to four weeks without having to charge the Freewrite.

Just My Type

retro typewriters writers

My Cup of Retro, $450

If electric typewriters aren’t your speed, My Cup of Retro is the shop for you. My Cup of Retro sells vintage typewriters dating back to the 1920s. Each typewriter has been restored to its full working condition. They are ready to use immediately and come with user instructions and full support. From portable typewriters to collectors items like the Hammond Multiplex typewriter ranging in a rainbow of colors, you’re sure to find the right typewriter for you.

Can’t Go Wrong with a Classic

retro typewriters writers

Classic Typewriter, $555

Specializing in the beautiful and the vintage, Classic Typewriter knows its way around a keyboard. This company is working to pair you with your newest writing tool. But before it’s sent to you, Classic Typewriter completes a 14-point inspection, ensuring its writability. Just add writer. These typewriters are categorized by day-to-day writing and portable writing. 

Death to Fascism, via Typewriter

retro typewriters writers

Iron Fox Typewriters, $400

Technology is killing individualism. At least that’s what the founders of Iron Fox Typewriters believe. Iron Fox custom paints and sells typewriters, or as they like to say, the machines that kill fascists. This company is all about preserving the past and forming the future without distraction. Writing, according to Iron Fox, is all about intention. You won’t automatically become the next Hemingway when you buy an Iron Fox typewriter, but it will start you on the path to greatness. Or at least to a really good looking piece of decor.

Straight to the Point

retro typewriters writers, $200 is more than, ya know, typewriters. They’re your go-to spot for all typewriter-related needs. Whether it’s transport motors or cleaning supplies, or vintage typewriters, has everything a writer needs. Well, besides the paper. All typewriters are packed and sold in their original packaging, and go through a reconditioning process before shipment. has sold and reconditioned typewriters since before there was a dot com (1958), so it’s safe to say they know their way around a clacking keyboard.