But I don't want to call attention to myself when I show up at the airport with just my purse. I'm trying to consider first impressions here.
Here's what I have planned:

That's the black shirred tank that I never get to wear because the neckline feels a smidge too low for work.

And there's the orange sheath dress that I love more than any other piece...with a hemline about a quarter inch too high for, you guessed it, work. I want to be Cathedral-ready for this trip, but it can't be harder than dressing for my job.

Those are pajamas. Pajamas! I usually sleep in my clothes to get one last wear out of them, but I'll be sharing a room and I'm trying to keep it classy.
The other items are
A yellow blouse that pairs with everything
A swingy navy blue tunic top
A black mesh cardigan for covering my shoulders in the cathedrals
Patterned palazzo pants
A red and turquoise (it works. trust me) patterned romper
Black skort
Yellow silk scarf in case I get cold, not likely
By my calculations I can wear each top three times, wear the dress alone once, wear the romper alone once, and I'm covered for an eleven-day trip. My companions will surely have noticed by the third wearing of the yellow blouse. Fortunately, I look amazing in yellow.
Shoes: metallic flats. I figure a closed toe is nicer than flip flops for the churches.
And now for the bag! Trusty blue backpack or stylish brown leather purse? Sadly, I think I know the answer. As much as I'd love to rock my leather purse all over Spain, my policy is never to travel with anything that I absolutely cannot bear to lose. (RIP, blue cotton lawn smock dress with tiny orange flowers that I accidentally left drying on the door handle of a hotel in Sarajevo. Six years on, I don't miss you any less. I've acquired new accessories that would pair so well with you. Grief is a spiral.)
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