Style Dilemma: What to Wear to a Winter Engagement Party

Babysis emailed me a while back, and this email string ensued:

Babysis: I need DC Celine. Engagement party in the city for Jack and Jill in mid January.

DC Celine: Lol. What do you want to wear?

Babysis: Don't know. Invite just came today. It's the first thing I thought about. I'm guessing probably skinny pants and a cute top or a little dress.

DC Celine: Dress. Definitely dress. Where is it? Restaurant? Bar? House?

Babysis: www.farmhousechicago.com, 5:00, cocktails and apps

DC Celine: oh, let's make this a fun style dilemma - haven't had a good one in a while

Babysis: It's all yours!

Did I mention that this was a while back? Yeah. December 19th. The party was a month ago. But, my stylish friends, that doesn't make this dilemma any less useful to those of us looking for that sort of in-between ensemble. A 5:00 pm cocktail party is dramatically different, in dress code speak, than one at 8:00 pm. On top of that, it's Chicago in January. Even if you were to don a LBD, tights (and a fur, for heaven's sake) would be an absolute must. Which, for this retro-minded girl, is not at all an issue, but a Chicago (heck, a DC one, at this point - brrrrr!) winter does possibly call for an elegant trouser of some sort. But though Babysis landed on an H&M LBD with a dramatic back (that's unfortunately no longer visible online), here are a couple of options at the ends of the spectrum.

Retro Black + White Dress: I'm a huge fan of dresses - one & done, so to speak. I loved the 60s feel of the graphic black + white shift I found on Pinterest, then recreated it with an Alice + Olivia Peter Pan-collared minidress, plaid patterned tights (you could just as easily do flat black, if you can't stomach the pattern), and Coclico booties, to keep it edgy, grounded, and, well, winter-appropriate.

Elegant Fur + Ladylike Trouser: one of my style crushes, Hillary of The Closet Party, pinned the fabulously chic cropped fur over a higher waisted trouser. To get the same feel, which would absolutely work for 5pm cocktails to honor a newly betrothed couple, I found a faux fur jacket at Nordstrom, a classic, cozy, cable knit turtleneck from J. Crew, their Hutton trouser in a grey similar to that in the original outfit, then a cognac bootie with a stacked wooden heel (for whom, an hour after I pinned it, I can no longer find it on the interwebs). Those booties might be my favorite part of the whole ensemble.

Tartan + Chiffon: I'm a sucker for plaid, and this pair of a classic red tartan with a black-on-black dotted chiffon blouse is spot-on (did I really just type that? I did. I'm sorry.). Kohl's has a pretty (and sequined) filmy blouse, and when you use a basic black tight under L.L. Bean Signature's just-as-classic Macleod of Harris plaid skirt, and my perfect Weitzman pump, you have a classic, wintry elegance perfect for toasting a newly bethothed couple.

What I've realized as I put these together? Barring the little extra bling many of us would switch out from a day at the office to go out for even cocktails (cocktail ring, sequined clutch, or a big medallion that would just be perfect with the turtleneck), these 3 ensembles are ones I'd personally wear to the office. 5pm cocktails call for a certain elegance, to be sure, but that elegance can be oh, so useful in the professional world.

Update: When I tweeted my post this morning, Nordstrom very nicely responded. I'm always a little awestruck when a large retailer takes the social media time to respond to something (but hey, that's what I hoped for when I included them in my tweet, right? Careful what you ask for.), but I took a chance and asked them about the Mystery Booties in the Elegant Fur + Ladylike Trouser ensemble. Sure enough, not only do they exist in This Season (always a challenge when you're repinning things all over Pinterest-Kingdom-Come), but they still have them, allbeit in a slightly different color. They're the Newbury Bootie from rag & bone.

I may not actually run to buy them (though I'm sorely tempted), as they're a steep (even for this shoe-a-holic shoe-anista) $495, never mind the reviews say they're a bit uncomfortable. That being said, the customer service lesson is one other retailers should heed: it took them maybe 30 seconds to look it up and track it down...and may have a sale because of it.