I go through a mental checklist when deciding on a location to take outfit photos:

1) Is there an object nearby so I can manually focus and set the camera? Open fields won't do.

2a) Does the spot have shade or is the sky overcast? Much preferred option. I find photos to have the prettiest bokeh background when I'm standing in the shade but the sun is shining bright behind me (example). Camera settings also seem to be easier to configure.
2b) Where is the sun in relation to the camera? With my back to the sun results in soft, glowy photos (example). Facing the sun usually washes out details. I have the most trouble with camera settings on this one.

3) Is the background pretty? Will the outfit clash with/blend into the background? Usually don't realize the latter happened until after the fact.

4) Will my shoes be able to handle the terrain? No to heels on sinkable surfaces, untreated leather on grass.

5) Are there a lot of people around? Depending on how self-conscious I'm feeling that day, I may or may not want to answer potential questions.

1 is a must. The object today is a log lying to the left of my foot. 2b and 3 are usually an either-or. Today's photo is the perfect example of having chosen 3 over 2b. Pretty background, but unfortunately I was facing the sun which completely washed out the details of the jacket. Sorry about that.

Have a great weekend, everyone!