Slacking Off

Why hellooooo there, loyal kittens! I apologize for being MIA this week, school+work+life has been kicking my bootay this week, and I just could not find time to take outfit pictures.
In lieu of an actual "this is what I wore today" post, I am instead asking (actually, begging) for your assistance in a matter of utmost importance.

Any of you who follow Elle of Joy, etc. (If you don't, do it. She's adorable) are most likely aware that the two of us are joining some college friends in NYC this weekend. It is sure to be a memorable time.

My dilemma, as usual, is that I can't decide what the eff to wear. The transitional weather is certainly not helping.

So, here's the break-down:

Weather: high 50s/low 60s, chance of rain
Itinerary: train ride, brunch, thrifting/wandering, wine bar, dinner, LES bar scene, breakfast, train ride
Objective: outfits that can easily transition between indoor/outdoor and from day/night

Right now, I'm leaning towards either a F21 dress or romper. I haven't had a chance to wear either of them yet and they have been staring me down from their respective hangers every time I open my closet.

Option 1: Dress (similar)
Daytime: black tights, black boots, black blazer (noticing a trend?)
Evening: swap boots for heels (probably black. hey, it's NYC nightlife. everyone wears black!)

Option 2: Romper (navy with green and white tulips)
Daytime: blue tights, kelly green over-sized cardigan, camel wedges
Evening: I'm stumped with this one. I would probably switch to my green flats, and swap out the cardi for.... something else? Help!

So yeah, as clearly evidenced above, I'm struggling a bit. Any words of wisdom from the audience? Feel free to suggest entirely different outfits too. I'm not completely hung up on these two pieces.

Thanks in advance!! My weekend bag loves you already (previously, I was planning on just stuffing her to the max with 5 different options).