The weather needs to make up its mind. Is it going to be cold and snowy? Mild and wet? Single digits in the AM but 45 on your lunch break?
Navy shift & floral jacket: I rarely like pre-packaged fashion sets and especially ones that consist of a jacket and a dress. I find the proportions of the jacket are usually pretty poor; they're often cropped at unflattering lengths. This set, though, is adorable. The jacket falls at a good place and you can't beat a classic white & navy color scheme. The poppy red accent really makes the set. Also? It's currently $42 at JC Penney's. Not a bad buy for spring.
Talbot's heart yoke sweater: When I think of 1980's preppy, this sweater is what pops up in my mind. Throw in a button-up, wide wale cords, and a Dooney All Weather Leather bag and you'll look just like my mom circa 1986. If you want to look more modern, add a pair of colorful pants.
Lafayette 148 ponte fit & flare dress: This dress just has so much going for it I actually (very briefly) considered spending the three figures for it. Sure, it's a few months worth of my clothing budget but I wouldn't need to wear much else. I mean, what can't you do with this dress? It dresses up, it dresses down. Heels, boots, red, navy blue, pink, etc. I just looked at it and instantly knew which scarves or necklaces I wanted to wear with it. Maybe if it goes on sale...
Talbot's Mackintosh: Here's another piece that screams "classically" preppy to me. It's not rubber, nor that flimsy nylon stuff that a lot of retailers try to pass off as a raincoat. I'd tell you to pick it up for the spring but as of press time it's all of eight degrees with two inches of snow on the ground. It's going to be 56 in two days. You might need it before March.