Now that we wrapped up the Mediterranean trip, Jenn asked "Could you revisit your "what to pack" post and maybe show all the ways you mixed together the items you did pack into different outfits? It would be fun and helpful for those of us with limited ability to do that."
Sure thing! Traveling the Mediterranean out of a carry-on bag for nine weeks turned out to be a breeze. The trick was having a mix of light tops that could be layered easily over jeans, leggings, a dress or a skirt. It would take me weeks to map out every combination, so instead I'll focus here on showing all the ways you can easily layer with a black dress.
The two black dresses I brought for the trip were quite opposites. A fancy black Theory dress with a nice a-line fit, a v-neck and pockets that I've had for years (similar to this black dress). The mid-weight suiting wool fabric did well with resisting wrinkles. And, also a very cheap black jersey racerback maxi dress from Old Navy (similar to this maxi dress). These two dresses turned out to be mix-and-match powerhouses for the trip.
It helps to keep the top layers light for wrapping and tucking into a belt. Also, it's helpful since they dry quickly after being washed in countries without dryers. The chambray shirt, pink sweater and rayon top were all featherweight. When it was cold or with the boots, I wore black tights along with the dresses.
More links: Silver cap toe flats in black. Versatile brown belt. Flat black boots. Chunky silver necklace. Featherweight pink cardigan.