Over the years, Jessica Simpson has given us a lot of fashion pain. Very little pleasure. So much pain.

Jessica stepped out in New York today. And this outfit, I think, qualifies as all pain. At the same time though… is it also pleasure? Because it definitely popped out at me when I was checking the updates at the photo agency. So, like, if it’s noticeable, if it stands out, does it mean the outfit has done its job? Does it mean she’s done her job? Her job, in wearing it, was to be mentioned, non?

So let’s take a closer look. For my taste, the skirt is too short. Maybe I’m not being fair though because, generally, my style vibe is anti-body-con. If you favour the body-con style vibe, however, the skirt itself isn’t the problem. The problem is the top and the way it’s being worn. If I were styling her I would have advised against blousing the top. Either pull it out all the way or choose a different top that doesn’t require blousing. Like a fitted tee or a cropped tee, to better show off the waist. That way you get the lines and the proportions: the breasts curve into the waist and the waist curves back out to the hips. Right now she’s stuck in the middle between body-con and baggy and neither side is happy.

And then there’s the sunglasses. The sunglasses are pretty cute. Unfortunately she’s wearing them with her hair down and these sunglasses need a lot more forehead. Right? Picture them with her hair all pulled back, on top of her head so that the wings on each end have room to spread. That way it wouldn’t look like it does now, like she’s wearing them too high on her nose. Outfits should be like essays or scripts. Where can I submit these notes?