I am on Team Keep and have several old midi dresses and skirts lying around. I have tried to style them in an updated way. What are your thoughts about these pieces? Other styling suggestions?

#1 is a dress, maybe 15 years old. It's rayon, with a Peter Pan collar. There are some fit issues (seen in the first pic--I think I'm too short-waisted for it) but I would wear it with a jacket, as in pic 2.

The second dress is quite long, almost verging into Maxi Territory? It's deep navy, from 1997. I remember precisely because I wore it once, to a beautiful evening wedding, with platform sandals and a pearl choker (with my hair up). I was about 6 weeks pregnant with my first child. Styled in the second pic for more of a daytime look. Is it too long? Worth shortening? I admit I feel quite swanky in this one :)!

The third skirt is from 1987. It's Benetton, made out of wool, and a vivid purple-blue. I remember I used to wear it with biker boots and an oversized black turtleneck. How does it look with the jacket?

I like the rugged short boots with the second two, but the gray may not be ideal. I am awaiting a UPS delivery with some short black boots that might work better, but I wanted to get your thoughts on these basic combos.

Thanks!!!

Okay, I just added a new pic of the gray dress in 1-2 with an edgier belt, bare legs, and ankle-strap black wedge sandals. Same jacket with sleeves cuffed and scrunched.Any better or still dated and not good?

This post has 6 photos. Photos uploaded by this member are only visible to other logged in members.

If you aren't a member, but would like to participate, please consider signing up. It only takes a minute and we'd love to have you.