I love the coated skinnies on you. I like the vest too. But I am a bit on the fence about the color. I think this brown does suit your skin tone ... But I am not sure if it is your best.

I don't think you look preppy (duh), but the piece itself is popular with preppy types. As you say, you can have a preppy gone wild dimension to your look. I'm not preppy but I do like some elements that are popular in a preppy look, such as Aran sweaters, turtlenecks, okay that might be it. I was looking at other vests, and found this one. I thought you might like the pocket placement and how it carves out a waist.

http://www.orvis.com/p/barbour.....gilet/14nc

I'm trying to attach a picture but my new ipad(!) is giving me trouble.

You look great in both pieces but I agree that the color of the vest isn't perfect - but it's not bad either, just more neutral, so it's probably more about how you feel in them and how it works with your wardrobe. I do like the color and style of that Orvis vest JAileen linked but not sure how that would fit and the price is nearly double.

Oh, JAileen, I love the color of the one you've linked! My concern is that the collar might make it less innerwear and more gear-like. I'd like to be able to wear this at the office without looking like I'm about to leave the building...

I was hoping to get a bit of the Mad Max look out of it - great call there. But maybe this vest just isn't the right one.