Cheryl Shops

Happy first day of autumn! For many of you, it's the time of year that a cold nip starts creeping in at night, and you start thinking about boots, sweaters, and pumpkin spice everything. Unless you live in San Francisco—then it's finally summer. After months of getting pummeled with wind and fog, we now get consistently sunny days and temperatures in the 70s, and it's glorious. Of course, it's also a little weird, because it's fall and you don't necessarily want to be parading around in bright colors and airy fabrics as you would in actual summer. Thankfully, I've devised an outfit formula that feels seasonally appropriate yet warm-weather friendly. Here's what to wear in San Francisco in fall. 

Free People Chelsea linen shorts

As I noted last year, I am not a big shorts person, however this might just be the pair to convert me. They are a revelation; I've been wearing them at least twice a week since I bought them. If you had shown me a pair of pleated linen shorts 20 years ago, I would have recoiled with disgust, but they are incredibly flattering—the pleats give the leg a bit of fullness that almost makes them feel like a skirt and avoids any thigh-bunching. The linen feels a bit dressier and more polished than your average pair of shorts, which makes them more dress-up-able. The waist is a bit on the higher side, so I recommend wearing them with a belt (I always love my Isabel Marant Lecce). Like most Free People items, these shorts are cut rather generously; I am wearing my usual size 6, and I like the looser fit, but you can always size down if you are looking for something more fitted. 

Frame blazer

My number-one rule of living in San Francisco is always bring a jacket—even if it's 80 degrees and sunny, once Karl the Fog rolls in around 5pm, you won't regret it. But instead of throwing on a denim or army jacket, I decided to elevate things a bit with my favorite lightweight blazer, which you last saw with red shoes. This one has a hint of linen for breathability, and the slightly oversized fit makes it feel a little more relaxed, so it's not totally out of place with shorts. This blazer is several years old, but I've linked to a more recent version; I'm wearing a size medium. 

Anine Bing tiger tee

You've seen this tee several times before—most recently with a quilted jacket—and while it's definitely faded a bit with age, I like how broken-in it feels. It keeps the entire look from coming across as too serious, which could have happened if I had gone for a button-down shirt. (Another good rule of thumb is to make sure you're wearing at least one knit.) Without the blazer, the outfit would have felt way more casual—it's a delicate balance. I'm wearing a size medium in this tee; I generally like to go up a size in Anine Bing for a little extra slouchiness. 

Celine Trio Bag & Topshop clog sandals (similar here)

I borrowed this #OldCeline bag from Wardrobe because I had a credit, and because I wanted to look fancy at Car Week (yes, we technically shot these photos back in August). It's actually snakeskin-embossed leather, and it's kind of a taupey-brown color; "the rules" would tell you not to pair a brown bag with black shoes, but rules were meant to be broken. In this case, I think the brown is a nice bit of contrast, and it helps to tie in the lighter color of the shorts with the darker blazer. I kind of wish Celine still made this bag (it's from the Phoebe Philo days) but you can still find it on resale sites like The Real Real, Rebag, or Fashionphile. As for the shoes, they are oldies but goodies; I think clogs are going to be huge for fall, so being a cross between a sandal and a clog, they're the perfect transitional shoe. Plus, the platform gives you a little lift, and every little bit helps when you're wearing shorts ;) 

OUTFIT DETAILS: Frame blazer | Anine Bing tiger tee |  Free People Chelsea linen shorts | Celine Trio Bag | Topshop clog sandals (similar here)