I'm in my twenties, so yes, definitely into fashion. And yes, I am proudly indulging in the trend of baggy jeans with lots of holes, and white Air Force Ones, lol. I enjoy a variety of things, and so does my husband. Since we got married, I began incorporating a lot of his fashion preferences into my personal style. He loves feminine clothing, so I have plenty of that now, too. To keep my personal style looking fresh and current, I take one or two popular items and start to incorporate them into my style. I will then stop wearing things that are considered dated (like skinny jeans), and save them in the back of my closet for when they become popular again.
Regarding denim shorts, I have a vintage pair of black, high-wasted cutoffs (orange tag Levi's) and I love them (and so does my husband, lol). Pocket placement is critical in order to achieve a lifted look back there.
Regarding Anna Bey, I don't care for her as a person; like others have stated, she's very materialistic (if some of you haven't, I recommend looking into her background). Regarding her personal style, it's a little stiff in my opinion, but it's not terrible. Honestly, whether or not a style looks good depends on the person wearing it. I've experimented a lot in my teens and 20's to understand what looks good on my body shape (my mom went to finishing school and worked as a model back in the 80's, so she learned a lot about fashion and how to make it work for one's body; thankfully, I had her help as well).