Cheryl Shops

I live in San Francisco, but I was born and raised in Chicago, and that's where I go every year for Christmas. Chicago is a lovely city, and I'd recommend visiting in the spring or fall; winter is an entirely different beast, although there's something so traditional and comforting about an actual winter. It doesn't look like we'll have a white Christmas this year—thanks, global warming!—but it will be cold. So Christmas in Chicago is an excuse for me to break out all of the wintry things I rarely get to wear in San Francisco. Here's what I'm planning on wearing.



It's been so chilly in San Francisco that I've been wearing this plaid coat nonstop (you recently saw it here with a black dress). I'm hoping I can get away with wearing it in Chicago, because I'm completely obsessed with it at the moment. I love that it picks up my favorite neutrals—camel, black, and gray—and just makes everything look so polished. Then again, maybe a more waterproof outer layer is a better idea. Either way, I'll be obsessively checking the weather until it's time to pack.



This is my favorite cashmere sweater. It's from Everlane, and it's several years old; you last saw it here. I recently bought their $100 crewneck (I'll be featuring it in an upcoming post) and this one is much softer. I'm wearing a medium—as with many of Everlane's sweaters, I like to size up for a slouchier fit. The color and the style are just so classic; I love this sweater so much, I kind of wish I could wear it all year, but being able to break it out around the holidays makes it that much more special.




I've also had this leather skirt for ages—this one is from Zara, but I've linked something similar below. It's a basic A-line shape with zippered pockets that are strategically angled to have a slimming effect on your hips. This one has kind of stretched out over time, as leather tends to do, but it's otherwise perfect, and I'll probably have it for another 10 years at least.



Accessory-wise, you've seen these before but they're just so good together. I love a little leopard print, especially against the plaid of my coat—it's a subtle way to mix prints, and still fits into my three guidelines for print mixing. You last saw the clutch in this post, and it's sadly sold out now, but I've linked a similar option below. And as for the shoes, yes, these are real Valentino. Yes, they were an investment. Yes, they are worth it. The gold on the shoes is so shiny (the knockoffs look much more dull), and they just make me so happy. I tend to save these for a special occasion (and last wore them with a LBD), but should probably wear them more. And for reference, I'm in a size 39—as with most European shoes, I go up half a size.



We shot these photos along Broadway in San Francisco, between the Lyon Street and Baker Street steps. Broadway is known as "Billionaire's Row", and as we were shooting, there was a crew setting up a structure (not a tent—I'm talking wooden posts and glass windows) in the middle of the block, presumably for a holiday party. Can you imagine being so rich that you can shut down an entire city block for your holiday party? Well, I can! ;)



OUTFIT DETAILS: Avec les Filles coat | Everlane cashmere turtleneck sweater | Zara leather skirt (similar here, vegan here) BP leopard clutch (similar here) | Valentino Rockstud pumps (also here)



Speaking of what to wear for Christmas, I've partnered with a bunch of my favorite bloggers to share our most festive outfits. Please stop by and say hi to all of these lovely ladies!