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
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I love wearing the combination of black and brown, especially if the latter leans towards amber. My mom knit me this chunky scarf last winter and it’s a go-to piece to add warmth to my winter attire (in terms of color and coziness). And, as I’ve mentioned in recent posts, I’ve decided to go for sturdier boots for the season, in an effort to make my footwear last longer than 4 months and to help my feet from becoming two ice blocks by the end of the day. I loved these Sorel boots when I spotted them – the color combo that always draws me in and so different and stylish, yet practical. Or are they? See Reality Check below.

Anthropologie dress | Sorel booties | J Crew hat | hand-knit scarf | Tory Burch handbag (sold out, similar style here) | DKNY tights | Michael Kors watch | Anthropologie earrings | antique button bracelets
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This is the first time in 60+ years that my family has spent time at the cabin during the winter months, therefore this also is the first time I’ve seen snow on that particular landscape or experienced ice on the lake. It was calm and beautiful on this day, and the bright white snow and horizon provided a crisp backdrop for this cozy black and gray outfit. I wear boots all the time these days, after realizing (finally!) that it’s just too difficult to keep shoes from getting trashed during Minnesota winters. But that means I’ve also had to search for some alternatives to my trusty Hunter boots, which are certainly the bees knees when it comes to sloshing through snow and slush, but also are on the expensive side if I’m just looking to add a color or style. I love the quilted look of these Sperry wellies, as well as the price point ($78.00, and I have to believe you can find them on sale somewhere this time of year!).

Banana Republic sweater, shirt and pants | Sperry Top-Sider boots | Kate Spade sunglasses | Eileen Fisher scarf | Tory Burch handbag (on sale) | Michael Kors watch | Melly bracelet | Anthrpologie earrings
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