A fine-rib knit turtleneck over a perfectly-timed plaid skirt just needs tights (and maybe a vintage Chanel belt) to be on-point for work all winter.  It’s an outfit that’s classic and comfortable, for those days when a power-look isn’t necessary (or maybe just hasn’t come back from the dry cleaner yet).

Where it really works overtime (I’m hilarious), is in the outfit add-ons that take it post-work and to any number of holiday-esque activities, effortlessly. These Stuart Weitzman lace-up boots are perfect for any and all seasonal activities, but not massively inappropriate for work like so many major shoe moments can be—depending on how formal your workplace is.  I should also mention that they are the single MOST COMFORTABLE BOOT I’ve ever owned. I feel like I could run a marathon in these suckers. Almost.

A smart top handle bag is all you need after-hours (your real bag can spend a night at the office, it’s fine), after that you’re just a pair of gorgeous gold statement earrings and a bold red lip away from being ready for a cocktail with a candy cane rim.  

Because it’s December and I’ve chosen to live my life outside of tropical climates (what was I thinking), a few warming moments are absolute musts.  I love a classic black beret, and, let’s just say, any headwear that allows me to cover up unwashed roots to stretch my blow out for an extra day is getting added to cart.  Paring this posh topper with a cropped faux fur jacket (this one’s Rebecca Taylor, which you’ll recall from this post), and gloves that actually have a really beautiful impact on the overall look (and are tech friendly!), keeps you warm and also maybe makes you feel like you cracked the code on how to stay truly toasty without feeling like you’re wearing a sleeping bag.