Okay, so I decided to heed the advice and start putting outfits together. After about the 10th incarnation I stopped adding all the possible top layers. It became obvious that I could pair the khaki moto or flowy black vest with most all of them. Most important was that I could wear any shoe option in case my feet really give me trouble. With that, I think I succeeded! And you'll notice everything fits in the bag barely larger than a kitty cat Even the shoes, scarf, undies, hat, belt, clutch . . . .Deep breath, here goes . . .

the outifts I had planned were
#1 for the daytime after I finish my race switching up a little to #2 for night
#5 for the plane trip there (wearing the boots so I carry less)
#3 for the day leaving and plane trip home (7pm flight)
#6 and/or 7 for Valentines late night music
#15 or #16 for renting bikes

So the green cashmere sweater and embellished black halter are just alternate choices particularly if it gets too cold.

Not pictured is my pink dress for Valentine's night which the BF will carry in his garment bag. I will pair the grey ruffle heels from #4 with it. So, that's the capsule. It sure does remix but I can't help but think I'm a little monotone. I guess that's the sacrifice if you want things to play well together lol.
Again, any thoughts on what doesn't work or any improvements, I'd love to hear it!! I did not add jewelry or my scarf, but they are packed along. Thanks for sticking this far with me