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Yes, I've done a few short story and poetry collections, as well as some plot prompt and recipe books where a bunch of loosely-related content had to be ordered. Two questions...
1) What were the criteria for the short stories being included in the book? They're all fantasy, of course, but was there any other unifying theme? Are they all your short stories? Were they all written at the same time, or in the same universe? List any qualifiers you can think of for each piece, because it will help you in making your decision.
2) Is your book going to be divided into any subsections, or is that something you're open to?
The reason I ask is because you may consider looking for sub-themes within the work and grouping it that way. If you have some that are more on the horror-fantasy end, and some on the humor-fantasy end, you'll want to group those together under a subheader so the change in tone makes sense. If they're all set in the same universe, you could group the stories by focus character, race, region, era, events in the timeline, etc.
If those more concrete distinctions fail, what I'd do is read each story and rate the "emotion" of the piece. Is it a happy, fast-paced piece? Is it a slow, world-building piece? Does it end on a tragic note? A heroic note?
Write out the emotional "roller coaster" for each story--draw little pictographs if you have to! Then look at each piece and arrange them so the overall emotional progression follows roughly what a full-length novel would.
Basically what I'm saying is that you want to use the emotional tones of each piece to play off of each other. If your audience reads the whole book in one sitting, you don't want to disrupt the flow by putting the most climatic stories at the beginning and the most trifling at the back. You want to start on a slower, world-building note and end on a heroic one. So if you put a few more humorous stories that introduce characters in the beginning, then some mixed ones that expose details and villains and twists in the middle, and then your most emotionally impacting ones at the end, you'll have mirrored the general progression of a novel.
You can then repeat the same process between each story. If you have one story that ends on a real sober, tragic ending, you probably don't want to open the next chapter with a tongue-in-cheek, irreverent story. The key is to reread your collection--or have someone else read it--once you've ordered it and see if any of the emotional "leaps" break the "magic" of the book, or if they help keep the reader immersed.
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