Cheryl Shops

As soon as I typed the title of this post, I thought, "how is it already October?!" Then I realized, "whoa, it's already October 13th," which made me wonder where the first half of this month has gone. The funny thing is, I feel like I haven't done that much this year, other than work my tush off, but that is quickly starting to change. Now that delta variant is on the decline (knock on wood), my social calendar is finally picking up, plus Sean has a bunch of conferences this fall that I'm going to tag along on. Then before we know it, it will be Thanksgiving, then Christmas and New Year's, and I don't know about you, but I can't wait for 2022 (according to Susan Miller, it's supposed to be my best year ever). That said, I am very happy it's autumn—I am one of those Fall People who loves turning leaves, pumpkin-flavored everything, and most importantly, fall clothes. October is really the sweet spot in fall dressing, because it's still warm enough to get away with a sweater and a light jacket. So in celebration of that, here's what I'm wearing in October.

It's funny how working from home has changed the way I dress, but in a way that you wouldn't necessarily suspect. The biggest thing is shoes, which as I've said many times already, I don't wear like I used to. I do, however, still wear a lot of skirts, preferably of the midi or maxi variety. I find them perfect for daytime, especially with a cozy sweater on top. And while I own several skirts that are similar to this one from the Nili Lotan x Target collaboration, I couldn't resist the fall-like print and the side slit. I'm so glad I got it—it's really comfy, thanks to the elastic waistband, and I think the cut is really universal. I'm wearing a size medium, and I'm glad I decided to size up, because it's pretty fitted through the hips. I feel like I can wear this one year round, and it will look especially good with tights and boots in winter. 

Another thing that's changed about my wardrobe is that when I went into an office, I wore a blazer nearly every day—nothing makes me feel more pulled together and boss-like. Now I kind of have to find a special occasion for one (and I own quite a few!), but I have been wearing them more as jackets when I meet friends for drinks or dinner. This J.Crew blazer is also kind of an exception because it's knit like a sweater, so it also can swing to the cardigan end of the spectrum. You've seen this one multiple times before (most recently with white jeans) and my one and only complaint is that the sleeves are too short, but otherwise I freaking love this thing and often contemplate getting it in another color (or several). I'm wearing a small—it's generously cut. 

Speaking of generous, The Sak gifted me this buttery soft leather tote bag. To be honest, I haven't carried a The Sak bag in a verrrrry long time (remember back in the '90s when everyone had one of their woven crossbody bags?) but I was pleasantly surprised by the level of craftsmanship in this beauty. The stitching details remind me of Bottega Veneta, and I think the tassel is super cute. Plus, the bag is nice and roomy—it fits my laptop without a problem—but it's not so big that it looks overwhelming. And there's just something so autumnal about carrying a serious tote like this one. 

There are so many shoes I could have worn with this outfit, but I decided to go matchy-matchy and break out my Chanel ballet flats, which you last saw in April. Again, I pretty much live in flats now, especially Birkenstocks and sneakers, but these feel dressy enough to wear out to eat while it's still warm enough for bare ankles. (I do enjoy outdoor dining but my feet often end up freezing, especially at night!) These shoes are an investment (they were my birthday present to myself this year) but they are so classic—and isn't that what fall dressing is all about?

OUTFIT DETAILS: J.Crew sweater blazer | Alexander Wang tee (similar here) | Nili Lotan for Target skirt | The Sak Los Feliz tote (c/o) | Chanel ballerina flats