XF 1.4 will upgrading overwrite my custom smilies?

If you are using the default style directory, yes.

You should use a custom style directory if you are using non standard images (of any sort).
 
Create a new style directory on the server and copy the files from the default style directory to it.

Then update the image path in the style properties.

upload_2015-1-14_11-6-29.webp

That will prevent your customised images from being overwritten when upgrading.
 
I modified the default style and I have put all of my smilies in the default smiley directory. I didn't think this was a problem though as the files have different names and extensions (they are all .gif whereas the default are .png).
 
As long as your smiley files have a different name and/or extension, that's fine.

If they are the same name and extension as the default files though, they will be overwritten when upgrading.
 
@Brogan out of interest, when I moved from phoBB to XenForo nearly 2 years ago (wow, time has flown!) I simply edited the default style to what you see today. At the time I thought it was the way to do it. Should I have created a new style and edited that instead? I didn't think it was needed and never use the default 'out of the box' style (and just create a new version of it if I ever need to test something).
 
You don't need to create a new style in the ACP - you can just edit the default style.
A new default style can always be created so it's not necessary to leave the original default style untouched.

However, if you are going to customise any of the style images then I would recommend having a custom style directory and then update the path as shown above.
 
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