We received this two-part question from one of our lovely readers:
I’m attending my boyfriend’s brother’s wedding in Chicago in early November. I’ve already selected my dresses for the wedding and dress rehearsal, but have yet to choose the shoes.
As the wedding will be in the fall and who knows about snow, I realize strappy sandals aren’t appropriate. At the same time, I don’t just want to wear standard black pumps, but I’m beginning to think that may be just as good a decision as any.
Our reader also sent along pictures of the dresses she’s chosen. The one on the left from Ann Taylor Loft and the one on the right by Donna Ricco from Nordstrom:

While you certainly can’t go wrong with a standard black pump, we do think there are some other fun options out there to go with the dresses you’ve chosen. We’ve picked three shoes that could add a little something to either or both of the dresses:
Metallic:

Since it will be too cold to wear strappy sandals, a shoe in a metallic ups the fancy-factor of the overall outfit. These classic pewter pumps could later do double duty by adding a fun punch to more conservative work looks.
Print:

Another route might be trying a patterned pump. Perhaps leopard? Or zebra?
Unexpected Color:

You might also consider wearing a pump in an unexpected color. A rich wine color, like this patent pump, would be a delightful twist.
The question continues:
Also, what do you suggest to cover up strapless/sleeveless dresses in the winter? A pashima, sweater type shrug? I know I’ll have to wear my black or camel peacoat from the car to the church/reception, but once I get inside I’d like to have a nice cover up that is elegant as well.
All of us are big fans of using pashminas as cold-weather formal wear wraps. With these dresses, we might suggest a charcoal wrap, perhaps with a tone-on-tone pattern. Another option might be to wear a thin, buttonless cardigan and belt it with a matching sash, like S. did when she went to the opera in San Francisco.
Whatever she chooses, our reader will certainly look lovely in these classic frocks!

I have a question on TOP of the questions here– and it seems silly to ask– but I feel like it’s just one of those things that I cannot figure out from fashion pics (like these dresses– which are great, btw). What do you were on your legs? When you look at these images these woman’s legs are bare– yet, a wedding in November in Chicago with bare legs? That would seems wrong. Black nylons? Tights might be too casual for this? NUDE nylons? I feel an instinctual wrongness about nude nylons… but maybe that’s just me.
Thoughts chicas?
As a resident of the upper Midwest, I would like to recommend my favorite winter party dress cover-up.
It’s best described as a giant pashmina wrap, but with two sleeves in it. So you put your arms in and then you can wrap, tie, or belt the loose ends lots of different ways.
I got mine a long time ago, but I’ve seen quite a few recently including at Victoria’s Secret and Ann Taylor.
I agree with poster #1. Bare legs+Chicago+November=cold! If the reader has room in her luggage I would actually suggest tall black boots for the black dress and cardi (if this is the rehearsal dress, not as formal as the wedding). And to really go “out there” for the wedding (blue dress?)…how about some cute booties? you could maybe do booties and tights for warmth if needed.
Ladies, thanks so much for the advice. I really appreciate you answering my questions!
Yes, bare legs…I’m thinking it’s a risk. But honestly, I just don’t think the tights look is quite as cute or elegant. Takes away from the dress and whole ensemble. Or perhaps, I just haven’t figured out how to correctly pair tights and dresses to make them fun and fancy.
Plus, I know I’ll be indoors for the rehearsal dinner, wedding and reception. It’s just the getting to and from that will be brisk. Hm…
AW-I do like the black boot idea for the dress rehearsal.
Two things that I have done while walking to formal events in cold, slushy weather:
1. Wear legwarmers, then slip them off like you would a pair of gloves when you get to the event.
2. If the bag you are taking to the event is large enough, why not wear some warmer/sturdier flats of some description while you are outside, then swap shoes once you arrive?
[...] may remember this gorgeous blue dress from our Reader Question post on what to wear to a winter wedding. Sassy Molassy (the reader in question) followed up with this [...]
She is really hot. Very sexy legs!!!! Sex on legs, stockings, nylons, , more of this girl please guys!