Need help with token creation!

Hey, person who's been nice enough to take time to read this. I've been DMing a Pathfinder game for my family for nearly 2 years running to keep us all together across some distance, and I've used Roll20 for most of that. As I go I get more adventurous with things, and I've wanted to make custom tokens for my family here and there. I use GIMP 2 and I've made some cool things, mostly by taking free tokens built by Devin Knight and modifying them. Like the bear token I made for my brother who was a dwarf-gone-werebear, and I used his dwarf token, removed the armor and stretched it to the bear token I found, drew a matching tower shield and threw on an axe.

My skills have got more refined since then, but I've run into a problem making a custom token for my other brother. He's the dude with a big sword. I think the token looks good, but when I put it into Roll20, it forces the whole image into one square on the grid and he becomes a gnome with a big sword. I want him to be appropriately sized for a medium character with his sword hanging out of the square. I've fiddled with the dimensions under the "advanced" menu from right clicking on the token, but that fix isn't very good. It gets sizing done appropriately, but with every move of the token it will offset the positioning out of the intended square.

I've seen and used tokens that fit nicely into a square on the grid and have swords and accessories that extend beyond the "5 ft" square.. how do I do that?

Note: None of my tokens are completely original, and all originals were free but not my own creative property. I do not intend to solicit any images for profit, and would accept no payment, but I would share those that I have made if anyone is interested, but please answer my question and help me size my sword-dude correctly!

In GIMP, increase the "canvas size". Make the canvas square no-matter-what shape the token is. Example: If the token is "tall" then it is a tall picture in the middle of a square (more blank space on both sides). If it is a token with a long diagonal sword, the square is big enough to accommodate the longest point so there's probably a large blank space on 3 sides.

Make the blank parts transparent, not white.

Save as PNG with transparency.

Upload tokens to Roll20. Place tokens on map. Resize tokens so that the "body" sits in the square you want, and the extraneous parts (the sword) stick out into other squares.

If it's not sitting in the square where you want it, go back to your GIMP file and adjust the position of the colorful figure within your square canvas area. Save it again and test it again til it sits like you want it.

Should work. Probably some more experienced token-makers can come along and give better tips and instructions.

Totally different answer here (hence different post, plus I thought of this after I wrote the above, when I re-read your question).

You know about "Shift-resize" and "Option-resize"/ ALT-resize? Try using Shift key, and/or Option-or-ALT key when you are resizing your token on the tabletop. Shift-resize lets you squish it in different directions out of proportion so you can fix the "gnome" problem.

Option-or-ALT-resize lets you place a token off-grid.

These techniques may help with your existing tokens rather than remaking them in GIMP.

Gold has the right idea, but personally I'd change the angle of the sword so it points upwards more, meaning the foreshortening will let you keep it all in one square.
Either works though.