JUST DON Snapback
Buy It Now at RSVP Gallery, $400
New Era Faux Snakeskin 9Fifty Snapback
Buy It Now at New Era, $30
Maybe you don't do formal hats. The ballcap got a luxury makeover thanks to Don C., and Kanye West helped make it a full-on trend. Rocking it with dinner jackets at high-fashion event, Yeezy successfully dressed down a formal rig while still looking like wealth.
While you probably can't cop a $400 snapback with the scrilla you make hawking pretzels at Auntie Anne's, it's a good thing New Era makes considerably cheaper faux snakeskin versions. That'll also help if your date is one of those idealistic, PETA-type girls. But if you happen to have a trust fund... by all means, spend that mommy-daddy money on the real deal.