Holiday Party Outfit Planning

One of the regrets of my sartorial life is that I have few real opportunities to get properly dressed up. Weddings come up in my social calendar once every few years, and I don’t attend a lot of galas, cocktail receptions and the like. Forget red carpets. Currently, my one chance to get fancy is New Year’s Eve; for the second year in a row, my husband and I will be attending a NYE party, sans kids, where the dress code is, well, flexibly formal. Which is to say, you can get as glitzy as you want.

As you can imagine, picking what to wear for such an event is an Important Decision in my world; I have a lot of “special occasion” dresses hanging in my overflow closet, waiting for their moment in the spotlight. This year, the struggle feels especially real, as there is no clear “front runner”. One decision that was easily made, however, was my choice of shoes. If you watch my IG Stories, you will have heard by now about my Cinderella moment at Goodwill – where I found a pair of like-new Manolo Blahnik “Sedaraby” pumps for a magical $12.50. In my size. In just the colour (black) and with the right amount of sparkle to go with pretty much any of my dress options. So, I had to get serious about the whole dress-picking thing.

I had two new (to me) dresses in the line-up this year, so I started there. With important occasions like this, I like to “test-drive” my options in advance and see how I feel about them – both whilst wearing them, and in photos. In some cases, outfits can truly look better in person than on camera, but for the most part, I find photos to be a really valuable tool in evaluating how a particular outfit works. For purposes of this exercise, and the photos below, I threw on some accessories, but they’re not necessarily reflective of how I would ultimately style these dresses (shoes excepted).

First up, this absolutely beautiful Armani Collezioni dress I thrifted in Phoenix this past May.

Pros: It’s comfortable (stretchy) and flattering; does not require Spanx; it’s over-the-top glittery and makes me feel like a fairy, shedding sparkles wherever I go (umm, literally). Did I mention the twirl factor?

Cons: It’s fairly conservatives (glitter aside) so I could wear this to more toned-down events (possibly even some work-related functions); it’s stretchy and loose, so will probably fit for the next few years – no rush on having to wear it; accessorizing can be tricky (potential for accessories to clash with glitter).

Second, this Tadashi Shoji number I thrifted in Calgary last November (I think).

Pros: It’s slinky, flattering and still fits (may or may not in a few years); the purplish colour is gorgeous though hard to capture in photos; the neckline is surprisingly comfortable, even with a strapless bra; easy to accessorize.

Cons: Would probably benefit from some Spanx; while lovely, it doesn’t feel particularly glitzy – feels more like a wedding party dress than a NYE dress.

After looking at these photos, I am leaning towards the Shoji dress as my first choice, but am not entirely sold yet. I’ve been looking through photos from parties past, and I find myself yearning for the bigger drama factor of some of my other dresses. Remember these:

Well, I can’t wear the one on the right because I wore it to the same NYE event last year, but the other two? Definitely in the running. Ugh, why is this so hard, you guys?

Are you attending any fancy events this holiday season? How do you go about picking what you’re going to wear?