I have this problem a lot, SilkCat, not only with Hermes bags but with clothing and shoes! I see something that I LOVE, but the cut/pattern/colors/fabric/heel height/etc. don't suit me for some reason. Maybe the heel is too high for me to walk, or the pattern is too loud for me to wear confidently, or the color washes me out, or the fabric is too heavy for comfort, or the garment is best suited for tea with the Queen or a debutante ball and I don't get the hoped-for invitation or or or . . . .
I have, sadly, wasted a lot of money buying things I admired because they were so pretty, and then never wearing them and later consigning them for pennies on the dollar with a sad and guilty heart. Sigh.
SO--a lot depends on your budget and your psychology! There is nothing wrong with buying something because it's pretty if your finances and attitude (and closet space) allow you to have things you don't use just because you enjoy owning them. But if that is not the case, generally I think it's best to go with what you feel you'll actually USE. Alternatively, sometimes I'll dip into an untried trend on the cheap and see if I actually make use of it, and if so, THEN I might splurge on the Hermes-level version. Of course, then there is always the risk that the luxury version will no longer be available when I'm ready to pull the trigger, but I've learned there will always be another pretty thing to covet, so I'm getting better at not giving in to FOMO.
So, er, none of this is very helpful to you, I'm afraid. But yes, I do know exactly what you mean.