Staff Member: Joe La Puma, Director of Content Strategy
Buy It Now At: Kith, $400 
Why I Bought It: "I got this at my friend Ronnie's store in KITH, and it was a combination of an impulse buy and him being a salesman. It's ridiculous to spend so much on a hat, but I justified it in a way that I'm a huge Giants fan, and not many people will have this specific hat when I'm tailgating at MetLife Stadium."