Unicode/Text App

Not exactly what you're looking for, but similar things...

In the Watch app on your iPhone, in Clock > City Abbreviations, you can change the name of your local timezone to "", and then have a complication that shows an Apple and the local time, and you can change your monogram to "" in the adjacent settings and get that to show if you use the "Color" face.

I actually set the local timezone name to nothing, so I can have an uncluttered digital local time complication on the analog faces, but i almost always end up using the Modular face.

if you can't get the actual "" symbol, you could copy/paste from this message, or google for "apple logo symbol", or, I get arbitrary Unicode characters from an iOS app called "Unicode Pro" (type "apple logo" into its search field).

(Technically, the Apple logo isn't a proper Unicode character, it's a "private use" Unicode character that Apple devices will show as an Apple symbol. If you read this post on a non-Apple device, you may see three instances of some completely different symbol, in quotes, up above.)

 

Unichar may fit what you need, it has a watch 2.0 app and of course a phone app. I used it to get my wife's fraternity symbol as her monogram.