And usually with a black concert shirt. And black on black Vans, which are pretty much what I wear exclusively (VERY rarely do I wear "grown up" shoes, and when I do, I have several simple pairs of ballerina flats)
Dresses! I only own one pair of jeans and I keep them for when I travel to Michigan to visit family. Even when we visit cold places like Munich or Krakow in the fall I wear dresses and tights. I love heels and wear them a lot. But if I'm going to be walking a lot, like New York City in the fall I wear a dress or skirt set with pearls, red lips, black eyeliner in a kind of retro way with cream or white eyeshadow and a bit of blush along with my fall coat and a pair of Sketcher Shape Ups that are really tennis shoes but look like dressy casual shoes. Not the most beautiful shoes, but they work when traveling, we walked 13 miles all over New York City one day and my feet didn't completely terrible that night, so that's a plus. I like to be dressed up and girly and it makes it easier for us to just stop into any nice restaurant we find while out on the town, even if there is a dress code. And if we are visiting somewhere where the dress code is enforced, like St. Peter's Basilica, I don't feel underdressed and I'm afraid of getting kicked out, they have signs that say no pants for women, even tourists. Pere Lachaise cemetery in Paris was a lovely spot to visit and we spent a nice afternoon walking amongst the sculptures and tenderly cared for graves and monuments and I felt more dignified in a dress because there were also people there burying their dead and I wanted to show respect. But mainly since I live in a tropical climate I wear sundresses or those funky dresses that have patterns on them and are terribly comfortable and soft, yet stylish. Jeans here hold in the humidity and would be very hot. Only tourists wear them here and only on the first day, usually, because they've just come from somewhere cold. Dresses are my comfort zone, jeans feel too heavy and constricting on me after years of not wearing them. But I love the way they look on most people and would like to find a great pair to have for Michigan visits, there is just something about an awesome pair of jeans that fit right in all the right places with a great black shirt. I'm so out of the loop, though, I don't even know where to start with brands!