A few nights ago I went to North Pond, a fancy restaurant I'd been wanting to experience for a long time, which has a "dressy" dress code. I had some fun debating what to wear for a hot night, a dressy place, and some walking in grass and possible bus-taking. Turns out we didn't have to take the bus, but that would have almost ruled out heels.
I have a few actually nice dresses, but mostly kinda frumpy shirt-dresses which I absolutely love, or overly-sexy yet too-casual jersey dresses. I have a bridesmaids dress which I guess I could wear, but it has short sleeves and is therefore a little too warm, and a really great vintage lime green & pink paisley dress. I bought it at the Gage Park Unique (best thrift store in Chicago) and it still had tags on it that said 100% silk, but then when I wore it my friends were convinced it was polyester, but it was remarkably cool and breathable, so I think the tags might be right. Anyway I hand washed it and tried to iron it, but I'm bad at ironing, and it still looks super wrinkly. I'm at a loss.
I've also got a pink dress with one strap that was my go-to fancy dress until I suddenly realized it's kinda stained and the sheer polyester chiffon-like layer has somehow shrunk so that when it's on, the top sheer layer is shorter than the underlayer of silk. It's extra-bizarre because when it's on the hanger, the sheer layer is a good couple inches longer than the silk, but then as soon as it gets on me, it shrinks up. I tried to stretch it out by clipping a pants hanger to the bottom and keeping it in the bathroom to relax in the humidity, which did nothing. (I now realize that this was a strange and overly-involved solution, which I continued rather than admitting to myself my unwillingness to learn to iron.) I finally realized I could iron it, which only partially worked and now the length of the sheer layer is uneven. I refuse to admit defeat. I have a picture of this dress from first year of college, but I hesitate to post it because it has two close friends in it, neither of whom have given me permission to put pictures of their 18-year-old dressed up selves on the internet.
I want something like this, by Mina Stone at Steven Alan.Or this, from Calypso St. Barth a long time ago.
Somewhat relatedly, I went to an antique market (it's like a flea market but way classier & more pricey) the other day and they had some Calypso stuff. They had a lot of incredible stuff, almost none of which I could afford. As I was telling my friend afterwards, my price range is: under $10. I did end up buying a great 50s full-skirt floral dress for $5. I have to take it in a little, and after that I'll be ready to take pictures.
Oh, and for North Pond, I ended up wearing a sleeveless navy blue velvet dress from Gap, which I bought at a yard sale in an alley a few weeks while waiting in line for Hot Doug's. I was unsure about velvet in the summer, but there ended up being a huge storm that cooled it down a lot, and it was cold in the restaurant. I also wore yellow heels (also from Unique) and a green floral silk bag (also from Unique) and a white pashmina that my boyfriend bought in Kenya and thought was a men's scarf, which I bet he could pull off but is definitely not the case. And a raincoat.