Before retirement I drove the same 21 mile stretch of 65 mph. highway for 37 years. In later years I saw more SUV's on their roof or laying on the side because of speed and inexperienced stupid a*s driving skills than any other car.
You said with your boyfriend's family? Ask his mom/sister to help you look right. But if they are takeing you tailgating you don't have to "dress to impress". This isn't a formal occasion. Don't over think this one. They may be more put off if you try to show off to much in your attire. But...
That would be AWESOME. And I don't care much for the NFL so I'd be pumped.
As far as the NFL goes, the owners would whine about not having enough billions of dollars and pay rookies less.