Could I still be hot?

My personal assistant is 21 years old and about to graduate from a famous music college which shall remain nameless--it's the one I teach at, and I don't need any trouble from them. She is a brilliant Renaissance woman who can play jazz piano like Oscar Peterson (and I am not exaggerating) She can sing in a unique, quirky jazz voice. She writes great songs. She takes photographs like a professional fashion photographer. She paints and makes films. She does everything well. She has been helping me to give my flagging performing career a shot in the ass. She got me in touch with a web designer who redesigned my website, she designed and printed business cards for me, she took hundreds of photos, and she got a special phone number that people can call to book me--they will get her on the phone. In theory this should all work like a charm, but I have not gotten any gigs as a result of this yet and it's almost a year. It is so exquisitely difficult to put yourself on the map as a musician at any age, and if you have not succeeded in doing so by the age I am now, you are at a distinct disadvantage.
The economic downturn isn't helping things. Being a jazz musician is 3 strikes against you right there. I have heard of bands that developed a following when they got a million hits on their YouTube video. They don't play very many shows. Apparently their young fans are content to download mP3s of their music. The question is: How do you come up with the next big thing song-wise?

There is also the issue of getting tired of playing jazz, which I have been doing for 30 years. While I love free jazz, almost no one else does. Playing standards no longer excites me after 30 years. And even when I was young I didn't want to be Diana Krall. I am now over 50 and I hope it is not too late to re-invent myself. I told myself I would never sing again, but it's a fact that singers are wildly more popular than the most accomplished instrumentalist. Lady Gaga knows this instinctively. Although she can play jazz standards, she sings (and extremely well) and uses the piano as a prop. When she does play, she plays minimally. It's all about the performance with her even though she has a lot of musical talent. She has created a persona in much the same way Madonna created Madonna, the difference being that Madonna has little musical talent. Even if I were to start writing catchy soulful R&B dance tunes right now, I would still be faced with the problem that even Madonna at age 50 doesn't look that great in her underwear on stage. Photos can be morphed with Photoshop (I look like a better version of my 21 year old self) but when you are onstage, you are...well, onstage in all your glory or lack thereof. I wouldn't have to go the dance route--I could do the Nora Jones thing, or the Sarah McLachlan thing, and be the pensive singer-songwriter. I am not sure if I am ready for this yet.
Although my assistant and my BF say I look hot, I don't quite believe them. I have never thought of myself as a beautiful, sexy woman. Thinking of yourself that way is 99% of it.

Last night I was on Facebook and one of my former students, now in his mid to late 20s, suddenly popped up on chat. He was flirting with me and apologized for being "inappropriate" when he said I should wear hot outfits when I perform and I would have a huge male following. He knows that I am old enough to be his mother, and in any case I am not contemplating cheating on my BF with him. But maybe he has a point and I could still give the illusion of being hot (as I see it--that isn't what he said.)
I need to experiment with some hot outfits. I also need to compose some hot songs and maybe start singing them. Or am I abandoning my free jazz dreams? is it possible to play free jazz, be popular with millions of young people, and be hot all at the same time? And do I have the courage to go that route?