I couldn't comment because I was out of town, so I'm starting this thread so that you know where I strand on the subject. I have posted about this a few times, and these posts cover most of my thoughts:
You need to dress in a way that is flattering TO YOU. You have to feel fab in your outfit, and that's the long and short of it. Identify your personal figure flattering priorities and adhere to them.
There is a tradeoff between wearing conventionally flattering outfits and wearing looks that are more fringe.
I think we ALL bat for Team Figure Flattery to a certain extent - otherwise we wouldn't be interested in fashion and style. Anna thinks her harem jeans are attractive (as do I) - otherwise she wouldn't wear them.
There is a HUGE difference between "less flattering" and "unflattering". I believe that stylish looks can be less than flattering - but they are still flattering (or flattering enough to be attractive). For example, I think my jodhpur jeans are less flattering, but still flattering. I would NOT wear them if I thought they were unflattering. I find too tight and too short clothes unflattering. Certain styles of cropped pants unflattering. Too much make-up unflattering. Unintentional sloppy fit unflattering.
Wearing conventionally flattering fits have nothing to do with attracting the opposite sex, or the same sex if you are gay. It's all about how YOU feel in your clothes. If you feel best in conventionally flattering fits - wear them! There is no need to look fringe, quirky, or more edgy just for the sake of it. Style must be authentic. I am not a quirky person. I would look and feel ridiculous in quirky outfits - although they suit others to the tee.
Wearing interesting outfits does not mean that you have to wear less flattering or unflattering outfits. You can totally where a conventionally flattering outfit and look interesting to my eye.
Last but not least - Figure Flattery is in the eye of the beholder. For example, I find surrendered waists, harem styles, dropped crotch points, slouch, baggy fits, extended (sharp) shoulders and low rises very flattering - when the details are right to my eye. I am not one to agonize about the shape of the back pockets on my jeans because they effect the shape of my bottom - because it's not a priority to me.
Okay! Back to having tea with my Papa. I'm scarce on the forum till mid next week.