San Diego in December: 19°C / 66°F afternoons, 10°C / 50°F nights, about 6 rain days, and every plan worth dressing for starts after a sunset at about 4:45pm.
Pack for the hours after dark. NOAA's figures for San Diego International Airport give December an 18.9°C / 66°F afternoon and a 9.9°C / 50°F night, with 1.67 inches of rain on about 6 days, twice November's total. The sun sets at about 4:45pm all month, and every fixed plan starts near it or after it: December Nights runs in Balboa Park until 10pm on the 4th and 5th, and the Bay Parade of Lights sets off at 5:30pm on the 13th and 20th. NWS San Diego's climate memo adds the wind: "Santa Ana winds commonly occur between October and February with December having the highest frequency of events." So pack leather over a knit, trousers that close at the ankle, and one skirt for the holidays.
December in San Diego is decided after a quarter to five. The afternoon wants a shirt; the lights in Balboa Park and the boats on the bay want leather over a knit.

Parade of Lights boats set off at 5:30pm on 13 and 20 December, about 45 minutes after sunset, and head for the pier at Cesar Chavez Park before turning toward Coronado. You watch from the shore as the air slides toward 10°C / 50°F. Olive leather stops the wind a knit lets through, and cropped to the waist it clears both the cargo pockets and the skirt's waistband.

Nights average 9.9°C / 50°F, and December Nights keeps Balboa Park open until 10pm on the 4th and 5th. A mid-grey crew knit under the leather jacket carries you through the last hours of that; on its own it covers a 19°C / 66°F afternoon in the shade. Grey sits under olive, navy and black without a fight, so it goes with every bottom here.

Start the day in this. A navy band-collar button-down handles 19°C / 66°F on its own at noon, then goes under the grey knit once the sun is down at about 4:45pm. With no collar points, nothing crumples under a crew neck or a zipped leather jacket. Button it to the top and add the gold chains for a dinner in Little Italy.

Gray whales show off Cabrillo from mid-to-late December, and the National Park Service names the heights around the Kelp Forest Overlook and Old Point Loma Lighthouse as the best places to watch. Khaki-olive cargo trousers take a phone and a folded map in the pockets, and the drawstring cuffs close at the ankle when the bay air drops toward 10°C / 50°F after dark.

December Nights runs from noon to 10pm on Saturday the 5th, ten hours on Balboa Park's paths and plazas. A chunky white low-top on a thick sole is the shoe for that, and for the Holiday Bowl at Snapdragon Stadium at 2pm on 28 December. White keeps the cargo trousers and the black skirt from reading heavy, and it stays visible in a crowd after dark.

One bag that swallows the knit. A slouchy tan leather shoulder bag folds a grey crew in beside your phone at 2pm, when it is 19°C / 66°F, and hands it back at five when the sun has gone. Gold hardware matches the layered chains, and tan is the single warm note against olive, grey, navy and black.

Christmas falls on a Friday this year, and the holiday dinners cluster around it. Layered fine gold chains turn the navy band-collar shirt into a dinner shirt, since there is no collar to fight them, and they finish the grey knit over the black skirt just as well. They weigh nothing, cannot crease, and travel in a sunglasses case.

This is the holiday piece, and one is enough. A black satin midi cut on the bias moves as you walk, takes the grey knit or the navy shirt over it, and goes under the olive leather jacket when a Christmas-week dinner ends at 10°C / 50°F. With the white sneakers it also handles December Nights, where you are on your feet until ten.
Navy band-collar shirt · khaki-olive cargo trousers · white chunky sneakers · tan shoulder bag with the grey knit inside. Cabrillo National Monument for gray whales from the Kelp Forest Overlook after mid-month, then lunch in Little Italy at 19°C / 66°F.
Grey crew knit over the navy shirt · black satin midi skirt · olive leather jacket zipped · gold chains · white sneakers. The Bay Parade of Lights at 5:30pm on the 13th or 20th, then dinner as the air heads for 10°C / 50°F.
A suggested look — Khaki olive relaxed cargo parachute pants with large side pockets and drawstring waist, Navy long-sleeve button-down shirt with band collar, Multiple fine layered gold chain necklaces, Multiple stacked gold-tone bracelets and bangles.

NOAA's figures for San Diego International Airport give December an average high of 18.9°C / 66°F and a low of 9.9°C / 50°F, with 1.67 inches of rain on about 6 days, about 3 of them above a tenth of an inch. That is roughly twice November's rain. NWS San Diego's climate memo names December as the month with the most Santa Ana wind events, and its 1961–90 table still gives December 73% of possible sunshine and a northeast prevailing wind. Daylight holds near 10 hours all month, with sunset at about 4:45pm.
An olive cropped leather jacket, a mid-grey crew knit, a navy band-collar button-down, khaki-olive cargo trousers with drawstring cuffs, white chunky low-top sneakers, a slouchy tan leather shoulder bag, layered fine gold chains and a black satin bias-cut midi skirt. That covers a 19°C / 66°F afternoon at Cabrillo, a Balboa Park evening that runs to 10pm, and a 10°C / 50°F walk back from the bay. Add a compact umbrella for the three or so properly wet days. Leave the wool coat, the suede and the sandals at home.
The City of San Diego lists December Nights in Balboa Park for Friday 4 December 2026 from 4pm to 10pm and Saturday 5 December from noon to 10pm. Friday is almost entirely after dark, since the sun sets at about 4:45pm, and Saturday is ten hours on your feet. Wear a thick-soled sneaker, and dress in layers you can open: a crew knit under a zipped leather jacket, cargo trousers or a midi skirt, and a shoulder bag with room for the knit. Nights average 10°C / 50°F, and the park keeps cooling until you leave.
Late December, if whales are on your list. Early December has December Nights in Balboa Park on the 4th and 5th; the middle has the 56th Bay Parade of Lights, which sails from 5:30pm on the 13th and 20th. The whales come after that. The National Park Service says "Mid-January is the peak time for migration, but whales are visible from mid-to-late December through March." Christmas falls on a Friday, and the 47th Holiday Bowl kicks off at 2pm on Monday 28 December at Snapdragon Stadium, so the last week holds both the holiday and the game.
December runs about 2.5°C cooler by day and nearly 3°C cooler at night. NOAA's airport figures give November 70.7°F and 54.8°F against December's 66.0°F and 49.8°F, and rain more than doubles, from 0.79 inches on about 4 days to 1.67 inches on about 6. Sunset barely moves, staying between about 4:40pm and 5pm across both months. November's capsule is linen under a Harrington; December's is leather over a knit, with trousers that close at the ankle. November carries Día de los Muertos and the Veterans Day parade; December carries the holiday lights and the first whales.
Workwear cut for a mild winter. Brixton began with a group of friends in a garage in Oceanside, and its first product was the Hooligan, a vintage-inspired newsboy cap; the label now makes headwear, flannels, jackets and workwear-inspired clothing, close to the December uniform here. Expect a flannel or a short jacket over a tee by day, a knit added at dusk, straight or cargo trousers and clean sneakers. For holiday dinners the register moves up one step, to a satin skirt or dark trousers under a knit, and rarely to a full coat.