Other than hipsters and their cafe racers, Motorcycles are not a popular cultural trend at the moment. I cringe when I say this but if HD wanted to jump on an opportunity they could produce a cafe racer sportster modeled around their 1965-67 bikes, priced for a 20 something with lots of addons and actually see some profit.
Yes a lot of current HD bikers would scoff at them, but I get those same annoyed looks on my VROD around some old timers.
HD needs to go further than that, the current entry priced harleys are a great idea but really lose out in looks and style. More effort needs to go in that to attract riders. Push harder on new rider programs and offer better incentives to graduates of said programs. Make those programs dirt cheap or in some cases FREE!
HD needs to invest in films, television or even YouTube channels that promote the brand and make it hip again. They have been trying for years with movies like the Avengers, and shows like Sons of Anarchy, but they need to push a little more and get more focus on the bikes themselves. I always said SoA failed in that regard because they never aimed the show at the gang's central love for the bike. In fact the bikes in most cases ended up being more of window dressing to all the guns, violence, and drama plays.
There is no doubt films like Easy Rider, The Wild One, etc really worked wonders inspiring young riders. I was even motivated to buy a harley when I watched the bike scenes in Terminator2 as a young teen.
The other issue beyond HD's control is that the middle class in the USA is getting crushed. The dollar is weaker, Taxes are higher, expenses, cost of living, job opportunites, etc are all on the downs. I was able to work hard and purchase my first home in los angeles in 1997 at the age of 23, no help from parents, just pure hard work and socking away money. There's no chance for 20 somethings to do the same thing in current times and I lay that on our elected leaders but that's an entirely different conversation.
HD has been on a financial roller coaster ride for a long time, they will weather this situation too. I hope they read this thread, or at least somebody hear could whisper the same words into the right person's ear who could do something about it.