I guess I'm destined to be a sensitive mess when I wear hats. I may go through phases where I'm all like, Yea, girl, we look good right now in this fedora — wear this hat out! But then I put on said hat with a less egomaniacal mind, like when I'm one foot out the door for work in the morning, and I begin to rethink the whole thing. What if this actually looks stupid. WTF what was I thinking, why risk the criticism? Do I look like Dark Man in this? BEST TAKE IT OFF. Insecurity eats me up whole and in a matter of seconds I become my worst enemy and convince myself that I am not a hat person on that day. Weekends are another story though. They're the playing ground for most outfits I deem too questionable for work until I get some proper mileage on them first. Long story short, that is what the above is. It's a test run for hats again because in this moment I'm 50/50.

J. CREW tux shirt (size 4) | J BRAND leather leggings (size 26, runs large) | J. CREW double monk strap shoes (size 7, runs large) | EVERLANE leather portfolio tote (similar, other colors!) | REPOSSI ring | FREE PEOPLE hat | ROLEX vintage | KATHLEEN WHITAKER earrings