You could sew two different ribbons together and set a grommet in the seam. That's basically how the original 4-color ribbon is. Even with the original ribbon you had to wind the ribbon to the middle and undo the ribbon from the vibrator and swap the side the middle grommet is on to change the color.
Via Ted Munk at https://typewriterdatabase.com/1969-sears-medalist-power-12.24661.typewriter
This was an easy service with the ribbon drive belt being the only issue. I used a 2 1/2 in O ring (link). The original V-belts are ok, so I am living with a little bit of hop in the motor belt.
Vintage Sears Celebrity Portable Typewriter Manual With Hard Case & Instructions<br /> by [[ShopGoodwill.com]]<br /> accessed on 2026-03-13T10:33:18
2026-03-12: 9 bids total with last minute bidding going from $82 (5 bids) to $128 with 4 additional bids for a Sears Celebrity typewriter with an obvious (photo of typebasket) double gothic typeface.
TypewriterMinutes - Typewriter Review: 1963 Sears Cutlass - YouTube<br /> by [[TypewriterMinutes]]<br /> accessed on 2025-12-26T01:20:57
https://old.reddit.com/r/typewriters/comments/1h4b3aw/is_there_a_source_that_exists_that_sells_or/
If you need them for basic functionality, often you can find the manuals of the original manufacturers' models for rebrands (example: the Sears Tower machines which were really just rebrandings of the Smith-Corona 5 series).
Additionally, after the 1930s there really wasn't a lot of new functionality, so almost any manual will help you to get you where you need to go, though there are some small differences in locations of things like carriage locks which can be helpful to know about and whose placement moved around on various machines.
You might also notice that as typewriters were more ubiquitous in the 60s and 70s their manuals got thinner and thinner with less detail. If you do find a specific manual, you're unlikely to find very much in it.
The Davis Brothers have some history on the Commodore line which was related to some of the Sears Chevron line. Polt does have two Commodore manuals which may be close to your machine: https://site.xavier.edu/polt/typewriters/tw-manuals.html
Taylor Swift uses a Sears Cutlass in All Too Well: The Short Film.
The Sears Cutlass is very similar to the Sears Citation.
New 1964 Sears Cutlass Model advertised in February 1965. The faceplate of existing examples exactly matches other machines only offered between 1964-65 (Citation, Constellation), so it is presumed to be exactly contemporary. Manufactured by Smith-Corona and similar to Smith-Corona "New 5-Series", with custom shell.