This seems easy. In truth it takes the basics: a top, a bottom, shoes, maybe some outerwear, and something to hold your iPhone/wallet/EOS Pomegranate Raspberry lip balm. Voila, right?
While I like keeping it simple, this is probably a little too reductive. This is especially true when trying to pretend it is Fall in the midst of San Francisco's un-PC-yet-infamous "Indian" (read "late") Summer.
Really it always comes down to the accoutrements. You have to mix and match the right accessories to achieve ideal body temperature and outfit quiche-ness. I'm advocating for you, trust me. Obviously open-toed shoes are pretty key if you want to do any sort of layering, but what you really need is a damn epaulette.
Going out at night, but it's too hot for a jacket? Wear an epaulette. Wearing joggers to work? Throw on an epaulette. Don't feel like leaving your apartment in anything more than some socks? Definitely add the epaulette--in San Francisco you probably won't be the most naked person outside anyways. Need I say more?