The skirt is a black, floor-length (because I'm short) polyester/rayon blend and comes from from Nordstrom's kids' section. The t-shirt is from my Birthright trip to Israel, so it has the easily-spotted Birthright logo on the pocket area and a large map of Israel on the back that is the entire length of my back. Not subtle, right? The gray shell is from Kosher Casual, my favorite shell supplier!
I always giggle when I wear this outfit, which happens relatively often because it is incredibly comfy while also being comfortable going between radically different temperatures. I basically lived in this outfit during the winter because even though this is a very lightweight skirt, it is very warm in the cold, but is almost equally comfortable in the heat.
But why does it make me laugh? Because I feel like a walking stereotype when I wear it. I look like a "frummed out" baal teshuva fresh off the boat from seminary in Israel. It screams "Born Jew!" so loudly that conversion has never come up in any discussion in its presence.
If you hear someone (especially young men) refer to a "seminary skirt," this is the skirt they mean. It is the sweatpants of Jewish femininity. Yet paired with a nice shirt, it passes as business casual in the secular world. If I could clone it, I would. I wish I had bought more than 2 of them.
On the other hand, the Birthright shirt suggests that I was not raised orthodox because most orthodox (especially modern orthodox) youth have gone on group trips to Israel before, which usually disqualifies them from Birthright's free trip. (Note that I qualified as a Jew as a conservative convert. Pre-converts are not eligible.) Even many reform and conservative youth are disqualified for the same reason. On the other hand, the pairing of the Birthright shirt with an orthodox-style shell and seminary skirt implies that Birthright affected me so strongly that I either stayed after Birthright or went back so that I could study in a seminary, maybe Neve Yerushalayim or Mayanot, both always popular with the BT crowd (For the record, I hear they're amazing). While studying there, you become observant and "frum out" according to the perspective of your friends and family back in the United States. They think you've gone a little crazy. And you think you've discovered the best thing since sliced bread. This causes you to talk about why observant Judaism is the best thing since sliced bread, which causes everyone to really think you're crazy, maybe to the point of avoiding you. Then over time, either you ditch it altogether or you mellow out and settle at your equilibrium of observance.
And that is what I saw reflected in the knowing glances from frum strangers on the street today.