@peregrinoHello, fellow hiker!  I work on REI's Virtual Outfitting team and size people for footwear remotely all the time.  I hope I can reassure you and make you feel more comfortable about ordering the 9.5. 

The most important clue you provide in your description is that you tried the 8.5 and your toe touched the front.  If you hadn't given them away already, I would have suggested you take the insole out of your shoe and stand on it.  That way you can see how much room is between the end of your longest toe and the end of that liner.  When we fit people in person, we look for about a thumbnail's width of space there.  If you were touching the inside of the shoe with your big toe, there likely would have been zero space.  A "thumbnail's width" is approximately 5 mm!  And a full size is approximately 5 mm.  Therefore, you need a full size bigger than you were in:  that is, a 9.5.  I do understand the hesitancy to buy another pair of shoes and the fear of having to give those away as well.  But I hope that this reassures you that only going up half a size from what you were in is not quite enough.  Once you bend your foot inside the shoe to step forward, your toes come forward, too.  You need room for that to happen.  If you'd still like to set up a virtual outfitting appointment before you order, we're happy to help further.  You can do that here:  https://www.rei.com/outfitting.  The appointments are free and use video to help confirm all the sizing details. 

However you decide to proceed, I wish you happy trails!

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