Highest grossing films of 2000 tend to disagree:

• MI:2
• Gladiator
• Castaway
• What Women Want
• Dinosaur
• Jim Carey Grinch
• Meet the Parents
• The Perfect Storm
• X-Men
• What lies beneath

Given this, I would say the coolest outfits would either involve plate armor, a volleyball, or a green yak-fur suit.

Making money != being cool.

If your sense of style is dictated by what is profitable, your style is consumerism.

“Cool” is subjective. But if you’re looking at a population, you need to look at what is most popular to determine what people think is “cool”.

Mass approval means mass acceptance. Mass acceptance means mass cool.

I can’t think of a better measure for what the majority of people like and think is cool, than cinema gross revenue. Because most walks of life enjoy the movies. Hollywood knows movie-goers vote with their wallets, or at least they knew that in 2000.

Hipsters weren’t gonna be cool for nearly a decade.

Iron Man wouldn’t come out till 2008, roughly the time the universe splintered and we got stuck in Timeline B. That was basically the beginning of the end of anything making sense. Now everything’s a reboot, a sequel, a sequel to a reboot, or a reboot of a sequel.

They are highest grossing because they sold the most tickets.

Uncool movies don’t sell the most seats.

It’s literally a popularity contest. And popularity contests are always given to the coolest.