On this trip I made shopping a priority and dragged the guys around to a few different places, all of which were amazing, but I had the best luck at Oak Street Vintage, where I scored a cherry-red 1960's raincoat for ten bucks, and this hat, which I adore so much I wrote a list about it:
1. It's dark green, which is almost as versatile as black but adds a subtle pop of color to any outfit.
2. Adjusting it like so means I only have to do makeup on one eye:
3. The frayed tag says "Made in Italy for Bloomingdales," a fact I brag about to random people on the bus, and they are always impressed.
4. Oh man, it's gonna take my karaoke rendition of Carly Simon's "You're So Vain" to a whole new level.

5. I can pull down the brim and walk around feeling glamorous and incognito, at least until someone taps me on the shoulder at the grocery store and says, "Winona? Is that you? Why aren't you wearing pants?"