San Francisco in December: 15°C / 59°F afternoons, 7°C / 45°F nights, 11 rain days, and the wettest month of the year at SFO.
Pack for rain and cold on the same morning. NOAA's figures for SFO put December at 14.6°C by afternoon and 7.0°C / 44.6°F at dawn, with 4.14 inches of rain on about 11 days, which makes it the wettest month of the year there, ahead of January and February. November got half that water, on 7 days. So the mackintosh now needs cashmere under it, the loafers need a lug sole and sealed leather, and the umbrella finally earns its place: 6.9 of those days clear a tenth of an inch. Sunset sits at about 4:50pm all month, and the city's plans move indoors to match. The Dickens Fair fills the Cow Palace on three December weekends, and San Francisco Ballet's Nutcracker runs from 4 to 27 December.
November asked San Francisco for the right fabric. December asks for the right fabric with cashmere under it, and, for once, an umbrella in your hand.

Start with the coat, because this is the month the rain and the cold arrive together: about 11 wet days and a 7°C / 45°F morning. A knee-length cotton mackintosh sheds a shower on the walk to the Muni stop and closes over a cashmere crew at eight. Single-breasted, so it wears open once the afternoon reaches 14.6°C. Cotton also dries overnight on a hotel hook; soaked wool is still damp at breakfast.

Wear this to the Dickens Fair. The fair's own line is "Costumes are Admired, but Never Required!", and grey herringbone Harris tweed reads Victorian at the Cow Palace without a bonnet or a frock coat. It is also the middle layer between the cashmere and the mackintosh, and on a Nutcracker night it is the jacket that walks over to the War Memorial Opera House.

Two degrees colder at dawn than November, 7°C / 45°F against 9°C / 48°F, and that gap is why this capsule carries cashmere instead of cotton. A heather-oat crew goes under the mackintosh on the walk to breakfast, under the tweed at the fair, and on its own indoors, where it is light enough not to overheat you. Oat against the stone coat keeps the day look pale on a grey street.

Collar out over the cashmere, cuffs showing at the wrist. A pale blue cotton button-down is what makes the crew look dressed at the Nutcracker, and it lets you strip to one layer inside the Cow Palace. Pale blue because everything else here is stone, oat, grey, navy or black, and one clear colour near the face keeps the look from reading as a raincoat and nothing else.

Navy hides what 4.14 inches of rain throws up off the sidewalk, and it carries both the tweed and the stone mackintosh without either looking borrowed. Pleats give you room to sit through a ballet at the War Memorial Opera House and to take the Filbert Steps up to Coit Tower at full stride. One pair covers the fair, the ballet and a Mission dinner, so the bag stays a carry-on.

A wet Muni step is where a smooth sole fails first, and in December you meet one on about 11 days. These penny loafers are black water-resistant leather on a lug sole, which grips the Filbert and Greenwich step-streets and still passes at the Opera House. A loafer rather than November's laced derby, because a wide pleated trouser falls cleaner over a low vamp.

Across the body, under the open mackintosh. A black crossbody with a rain flap keeps the phone and the ballet tickets dry on the walk from Hayes Valley, and it leaves both hands free for the umbrella and a railing on the Filbert Steps. Black matches the loafers and the umbrella, so the only colours left in the look are the pale blue collar and the oat knit.

Our October guide said skip the umbrella, and November's trusted a cotton trench. December is different: NOAA counts 6.9 days at SFO that clear a tenth of an inch, and that is rain you stand under at a bus stop rather than walk through. A compact black one folds away between showers and opens again outside the Cow Palace when the fair closes at six.
Stone mackintosh open · heather-oat cashmere over the pale blue button-down, collar out · navy pleated trousers · black lug-sole loafers · rain-flap crossbody · umbrella closed. Coffee in Hayes Valley at eight in 7°C / 45°F, then the Ferry Building before the next shower.
Grey Harris tweed over the cashmere · pale blue collar · navy trousers · same loafers · mackintosh buttoned · umbrella up. The Dickens Fair until it closes at six, long after a 4:50pm sunset, or dinner in Hayes Valley before the Nutcracker at the War Memorial Opera House.
A suggested look — stone mackintosh, heather oat cashmere crew over a pale blue shirt, navy wide-leg trousers, black lug-sole loafers.
Cool, and the wettest of the year. NOAA's figures for San Francisco International (SFO) give an average December high of 14.6°C and a low of 7.0°C / 44.6°F, with 4.14 inches of rain across 11.1 days of measurable rain. About 6.9 of those days bring a tenth of an inch or more. That puts December ahead of January and February at SFO, and NOAA's Downtown station records more still: 4.76 inches on 11.6 days. Daylight shrinks from 9h 45m on the 1st to 9h 35m by mid-month, with sunset about 4:50pm throughout.
A stone cotton mackintosh to the knee, a heather-oat cashmere crew, a grey Harris tweed jacket, a pale blue cotton button-down, navy wide-leg pleated trousers, black water-resistant penny loafers on a lug sole, a black crossbody with a rain flap and a black compact umbrella. That covers a 7°C / 45°F walk to breakfast in the rain, a 15°C / 59°F afternoon with the mac open, and an evening at the Nutcracker or the Dickens Fair. Leave suede, the down parka and shorts at home; 11 wet days and 7°C mornings rule out all three.
Clothes you can walk in from 10am to 6pm. The Great Dickens Christmas Fair, running since December 1970, fills the Cow Palace in Daly City on five weekends from 21 November to 20 December 2026, plus the Friday after Thanksgiving, and its policy is plain: "Costumes are Admired, but Never Required!" If you do dress up, stay Victorian. The fair bans full-head masks and non-Victorian costumes such as Star Wars or superheroes, and asks guests not to come as its central Dickens characters. A tweed jacket over cashmere nods to Victorian London, and the mac covers the walk out after dark.
The first three weeks, for most visitors. San Francisco Ballet's Nutcracker opens at the War Memorial Opera House on 4 December and runs to the 27th, but the Dickens Fair closes for the season on 20 December, so only a trip before then gets both. The fair's December weekends are 5–6, 12–13 and 19–20 December. The light barely moves: sunset holds at about 4:50pm, and sunrise slides from just after seven to about 7:25 by the 31st. The rain is a whole-month figure, 11 wet days in 31, so pack the umbrella whichever half you choose.
Colder and twice as wet. NOAA's SFO figures give November 18°C / 64°F afternoons and 9°C / 48°F mornings with 2.04 inches on 7.2 wet days; December drops three degrees by day to 15°C / 59°F and two at dawn to 7°C / 45°F, with 4.14 inches on 11.1 days. Our November guide argued that the month changed fabric, not temperature. December changes both, so the cotton trench becomes a mackintosh with cashmere under it, and an umbrella joins the bag. Daylight falls from about 10h 10m to 9h 35m.
Layers from the city's own labels, built for rain and hills rather than snow. Gap started here. Gap Inc.'s history for 1969 reads: "Don and Doris open the first Gap store at 1950 Ocean Avenue in San Francisco, California." The local register is still that plain: a pale blue button-down under a crew, navy trousers, a mac on top. Timbuk2 began in 1989, when bike messenger Rob Honeycutt made the Classic Messenger Bag in the Mission District, and a bag worn across the body, flap down, is the messenger's habit carried into the rest of the city.