The wedding:

• Sculptural LBD: Ann Taylor summer mega-sale
• Painted Cashmere Wrap: mommed
• Stockings: Spanx (sorry!)
• Black Croc Wedges: Stuart Weitzman, via Bloomingdales
• Necklace: David Yurman, gifted

As I mentioned yesterday, we had a joyous-if-frigid weekend here in Narrowly Tailored-land, highlighted by the beautiful wedding of best-friend-from-law-school A.! A. and husband(!) J. are such special people, and it was a joy to be a part of their wonderful ceremony and to share the weekend with them, their families and friends.

Although A. and J.’s church doesn’t have a strict modesty code, I was giving a non-secular reading, so it was important to me to be respectful of the setting and their tradition. In retrospect, a cardigan in a bright color might have better served this purpose (covering my shoulders more permanently and keeping me warmer on what proved to be a bitterly cold night). All the same, I liked cozying up in this wrap I seem to have relieved my mother of some years ago (I think under the guise of borrowing it for someone else’s wedding — thanks, Mom!), which added a unique texture, some visual interest and some old-school glamour to the ensemble.

Hindsight is 20/20, but I probably should have styled this look with bolder, higher heels in a sexier shape (either a plain stiletto pump or perhaps my black tweed heels). I plead practicality: my black “office heels” need some TLC after a summer of walking up and down city sidewalks, and the tweed heels seemed a bit, well, dangerous for a walk across the church and up carpeted steps to the dias to read. All the same, I think the patent croc leather added a bit of unexpected glam to the toned-down silhouette of the wedge heel: it probably isn’t a look I’d make a mainstay of my semi-formal wardrobe, but here, I think it worked.

In re: my office heels: what’s your cost-benefit equation when it comes to repairing inexpensive heels? I can’t decide if it’s worth paying $20 to repair a $45 pair of shoes, investing more sensibly in such a critical wardrobe piece, or some alternative solution.

The rehearsal dinner:

• Floral Patterned Jersey Dress: Boden (UK) semi-annual sale
• Maroon Tights: HUE, via hue.com
• Brown Riding Boots: Franco Sarto, via Zappos
• Necklace: David Yurman, gifted

These outfits are actually in reverse chronological order: I wore this one to the rehearsal, rehearsal dinner and accompanying festivities. I had been struggling with what to wear for Friday’s events, which fell into that dreaded “festive casual” / “just look nice” dresscode wasteland between “flirty summer frock” and “semi-formal attire,” particularly in the dead of a mid-Atlantic winter. As if sensing my sartorial malaise, the dress I ordered from the Boden sale showed up on Thursday evening, giving me a brand new option to wear on Friday (and to experiment with in the weeks and months to come). (Ed. note: if you order things from the UK, you usually cannot track them unless they’re shipped UPS or Fed Ex. On the other hand, bonus excitement when your stuff eventually shows up weeks later….). My original plan was to pair this with nude microfishnets and either red or teal pumps, but after taking a look at the weather and the 2+ miles I’d be walking across the city, I opted for boots and colored tights.

Even though it’s fitted through part of the torso, this dress probably could have used a belt to better define my waist and tie the brown boots in to the brightly colored ensemble. I struggled with how to belt around the under-bust seam: any ideas? How do you belt dresses with detailing in the form of ruching or seaming?

As veteran readers know, I’m not exactly known for my vast collection of printed items, and this is by far the boldest print I’ve purchased in recent memory (and, let’s just say I have a long recent memory!). I loved its festive, energetic vibe, and I’m looking forward to pairing it with other prints, as well as other bold solids. I’d love your thoughts, though: how would you style this dress? How do you dress for those kinds of “in-between” occasions, particularly during the colder months?