I've never documented how I do this before, but being that the first time I have, it was a 40K design, let's roll with it. if you're impatient just hit the bottom of the topic.
So you start with an image (hopefully a lineart) that you wish to turn into a sewing.
I doodled up this sassy misappropriation of commissariat equipment. As this is B&W the shading is drawn in, which makes this look pretty ugly. Because of the roundness of stitching you gotta over exaggerate certain shapes like arms and angles.
So you take that image, and put it through the embroidery software's first step. Whereupon it turns into a rough approximation of utter ass.
The next step roughly vector-traces it, and I mean roughly. You get gaps, double runs and tomfoolery. I didn't snap a pic early enough. This can take anything from 5 minutes to several days. thankfully because I designed this one, it took about 15 min. Worst I ever had was a week on and off, working from an old photocopy.
Everything is linear, point manipulation, so when that lovely circle ends up looking like crap, you gotta fix it back up:
Not gonna bore you with stitch density settings, but now you layer in the fills and outline stitches. Dotted lines are where things overlap but have no outline. This part takes the least amount of time and is the best way to utterly spanner up your entire design if you don't understand stitching.
Now you can do a rough digital preview. Are there actually gaps under the arms?
Yes ok.
Then you stuff the file into a machine, and the machine makes you cry, and you get this.
Well actually, you get this first:
What happened here is a brain fart where I used blue material. You can see what happens if you run too many stitches into a small area. It's much like ink saturation, your material eats itself.
Now you too can go deaf at an early age with industrial sewing! Go create!
All stitched up: 40K Embroidery
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That's so neeaaaat!!!!!!!!!!!!!!!!! :OOOOOOOO
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I used to work on hoodies and such, very rarely my own designs, so this was a blast. All my stuff is packed away until mid Feb, but I'm hoping to have some fun with designs again soon. Might see if I can do some tiny flags.

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Man... That would have been a great Warhammer 40k gift for my Christmas
If you like to Read up about my OC ->
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- Commissar Cat
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Glad you like it.
And here's an older piece that wasn't my original design (you may recognize it as a scan of the decal the GW gave out for a while), but shows a little more of the process.
Skipped all the cleaning process pics because dull.
Here you can see all the various settings to adjust for one section of sewing. It's blurry so you don't steal my secrets- I mean actually because it's amazingly dull. This is the fill setting for just one half of the skull. If you leave them on automatic, bad things happen.
Digital preview, again the stitches are never really rendered correctly, this just checks it doesn't look like Satan barfed on your fabric (which is a thing).
And then I test it on a dice bag before wrecking a hoodie.
Brrrrmmmmmm. (1200 stitches per something)
And done. Don't forget to sew up the bag and give it away without taking a picture of it when it's completed. That is an esstential step.

And here's an older piece that wasn't my original design (you may recognize it as a scan of the decal the GW gave out for a while), but shows a little more of the process.
Skipped all the cleaning process pics because dull.
Here you can see all the various settings to adjust for one section of sewing. It's blurry so you don't steal my secrets- I mean actually because it's amazingly dull. This is the fill setting for just one half of the skull. If you leave them on automatic, bad things happen.
Digital preview, again the stitches are never really rendered correctly, this just checks it doesn't look like Satan barfed on your fabric (which is a thing).
And then I test it on a dice bag before wrecking a hoodie.
Brrrrmmmmmm. (1200 stitches per something)
And done. Don't forget to sew up the bag and give it away without taking a picture of it when it's completed. That is an esstential step.
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Well now you've gone and done it. Andromeda just swooned over your Icon Mechanicus.
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SHUT UP AND TAKE MY MONEY!
Doing the work of the Emperor is its own reward.
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I only ever do these things as gifts, I'm afraid. Rather stay out of all that kind of thing. 

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Doing the work of the Emperor is its own reward.
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