Since it's cute and warm enough for transition weather, I'd love to try the leggings-with-denim-shorts trend. The black leggings are slimming, making your legs feel longer, and you get to feel sexy in shorts without having to worry about showcasing any cottage cheese thighs (or pale, unshaven winter legs. I know I can't complain about paleness, but still...).
On top, I love the idea of working in more layers to the things I wear as well. The J Crew boyfriend cashmere sweater looks gorgeous and oh-so-comfy. And we all know I have a space in my heart for comfy jumpers. And I like that with the right layering, you can dress up that v-neck heather grey tee just enough for a playdate, play group, or a post-library coffee shop run. Bonus? If you go just the button-up route, it's brilliant for breastfeeding in public without having to show off your post-pregnancy tiger stripes. :)
Also, that watch is rocking my socks off. Ignore the fact that the StoreEnvy page says that those Roman numerals around the face are apparently Arabic (come on, people, it's not difficult!): this is the sort of thing that could persuade me to actually wear a watch. Some time soon, I'll definitely have to elaborate on what I think makes a good watch...speaking as the pickiest, most finicky person about watches and wrist-wear generally.