"Cute on some hipsters, gangsters and the occasional supermodel. On the everyday person, they just make it look like you are trying too hard to be cool."
This weekend, I learned to eat my words. We were in NYC for a wedding and stopped by a place called Tillman's for a drink and a quick bite. Filled with dapper bartenders, clubby U-booth alcoves and hip wall art, this spot oozed of Coltrane and Harlem reinvented. We were served by a gorgeously classy girl wearing...a fedora! And man, did she pull it off. She called me "the lady" and brought me a perfectly constructed Old-Fashioned, which I sipped with a gourmet chèvre and roasted tomato sandwich, along with a side of scrumptious black eyed peas and handmade spicy potato chips. Sundays this bar features live jazz, and I bet late in the evenings it's one fun spot to drink some classy cocktails while people watching. I highly recommend either activity.
In any event, I will now jealously think about how damn good that fedora looked on our waitress, in a totally hip (without being hipster) kind of way. And believe me, she wasn't trying hard to be cool. She just was.
165W 26th Street
New York City