I used to have some fancy holiday parties to attend during the holiday season, but that’s not so much the case anymore. I no longer have an office evening party, the corporation having scaled back to a toned down luncheon when the economy tanked in ’08 – and even though the market is back up, the fancy party remains nixed. And our weekday plans have me spending my time figuring out parking for the kids’ holiday programs rather than figuring out the perfect holiday dress. When we do go out, it generally leans toward relaxed and casual, such that I’m usually trying to find ways to dress up some of my normal attire just a bit, to make it appropriate for a holiday occasion but not be over the top. I purchased this dress at the end of the summer and wore the heck out of it in the warmer months – mostly in casual settings. But pairing it with a fun and fancy winter coat, tights, heels and cocktail jewelry take it into holiday wear.

Madewell dress (now on sale) | Topshop jacket (now on sale) | DKNY tights | Trina Turk shoes (on sale) | Tory Burch handbag | Kate Spade sunglasses | Banana Republic necklace | Pelago cocktail ring | Tory Burch earrings | Michael Kors watch

Reality Check.  I brought this outfit with me to wear to a retirement party of a family friend (see, that’s the kind of party we go to these days) and ended up changing right before the event because we had unusually warm temperatures this weekend and this faux fur number is way toasty. But here’s my point: I’m not sure when I will wear this jacket. I feel like the outfit is a bit like one from this summer (link here) where I like it in theory and in pictures, but feel a little silly actually pulling it off in my reality. Perhaps I will change my mind when the temperatures dip below 10 degrees again and I want an alternative to my parka.