Sydney in December: 26°C / 79°F afternoons, 18°C / 64°F nights, and a New Year's Eve that runs from a 10am gate to a 12:30am exit with no sunshades allowed.
Dress once, for fourteen hours. NOAA's figures for the Bureau of Meteorology's Observatory Hill station put Sydney's December at 25.7°C by day and 18.4°C at night, with 73mm of rain over about 10 days, and the Bureau's own long record gives the month the year's strongest mean 3pm wind, 19.5 km/h. The Sydney to Hobart fleet leaves at 1pm on Boxing Day. Five days later, on its published hours, Mrs Macquaries Point opens at 10am for New Year's Eve and closes at 12:30am, with no sunshades and no re-entry. Sunset is at about 8pm. That leaves about ten hours of daylight under only the shade you wear: long linen sleeves, a brim tied on, a dress for after dark, and a bikini for the beach days either side.
On New Year's Eve in Sydney there is no shade to put up and no way back in. What you wear through the gate at ten in the morning is what you sit in at midnight.

Sleeves down from 10am, because Mrs Macquaries Point allows no sunshades and the only shade you get on New Year's Eve is the shade you wear. Cancer Council Australia rates pale shades below navy or dark red of the same fabric for UV, so this shirt earns its place by sleeve length and linen weave, not colour. Knot the tie front over the gingham and it stays cool at 26°C / 79°F.

One dress for three dates: Carols in The Domain on Saturday 19 December, 1pm to 11pm; Christmas lunch on the 25th; and the 9pm fireworks on the 31st, under an hour after sunset. Green-and-white check hides the grass marks from a day on the lawn. Front pockets take a phone and a card, so the bag stays shut in a crowd of up to 10,000 on the point.

Pack it for the beach days on either side of Christmas, and swim in this rather than the shirt: Cancer Council Australia warns, "Fabrics offer less protection from UV radiation when wet." A high waist and a square neck stay in place through a Bondi shore break. Dry off first, then put the linen back on over it for the walk up to lunch.

Wear them from the towel to the water and on the way out to Watsons Bay, one of the land viewpoints the race organisers list for the Sydney to Hobart start at 1pm on Boxing Day. A flat H-strap slide comes off in a second at the sand line. Tan raffia sits under the cobalt bikini and the gingham alike, so one pair covers the beach half of the trip.

Red leather is the capsule's one strong accent, and against green gingham it says Christmas without a novelty print. A strap across the instep keeps a mule on through a day of getting up and down from a blanket, and on the walk out after the midnight show. Keep the heel low: a stiletto sinks into the steep grass on Observatory Hill, which opens at 2pm.

Wear them scrunched over the mules. On its published hours Mrs Macquaries Point runs from 10am to 12:30am, fourteen and a half hours, long enough for any leather strap to rub a blister, and a thick rib takes the friction. Cream picks up the white squares in the gingham, so the socks read as part of the outfit rather than a repair.

The cord is why this hat made the list. The Bureau of Meteorology's long record gives December the year's strongest mean 3pm wind, 19.5 km/h, and 3pm on New Year's Eve finds you on an open lawn with no sunshade allowed. A brim that goes all the way round shades ears and neck; the black cord keeps it on, and lets it hang down your back after sunset.

City of Sydney's viewing guide warns that large bags are often banned at vantage points, and most do not let you back in once you leave. A straw bucket with a leather top handle holds the sunscreen, water and snacks on the guide's list, and very little else. It matches the hat and the slides, so straw carries the whole day.
Pale pink linen shirt over the gingham dress, sleeves down · cream socks · red Mary Jane mules · corded straw hat · straw bucket bag. Through the Mrs Macquaries Point gate soon after 10am on 31 December with a blanket, then lunch on the lawn.
Gingham dress · cream socks · red Mary Janes · pink shirt knotted round the shoulders · hat down your back on its cord. Sunset at about 8pm, the 9pm fireworks from the same patch of grass, then midnight, and out at 12:30am.
A suggested look — Sleeveless square-neck mini dress in bold green-and-white gingham check with front pockets, Vibrant red mules with low heel, Thick ribbed cream crew socks.

Warm, with long days and a steady afternoon wind. NOAA NCEI's figures for Sydney Observatory Hill, a station the Bureau of Meteorology operates, give an average December high of 25.7°C and a low of 18.4°C, with 73mm of rain across about 10 days of measurable rain; only about 6 of those bring more than 2.5mm. The Bureau's longer record at the same station gives December the strongest mean 3pm wind of any month, 19.5 km/h, and about 7.6 hours of sun a day. Daylight runs from about 14h 15m on 1 December to 14h 25m from mid-month, with sunset near 8pm.
A pale pink long-sleeve linen shirt, a green-and-white gingham mini dress, a cobalt high-waist bikini, tan raffia slides, red low-heel Mary Jane mules, thick cream crew socks, a tan straw wide-brim hat with a chin cord and a straw bucket bag. That covers a 26°C / 79°F beach afternoon, Christmas lunch and a fourteen-hour New Year's Eve on a harbour lawn. Add sunscreen and a thin rain layer: City of Sydney's viewing guide lists wet weather gear, and about 6 December days bring more than 2.5mm. Leave the jacket, the pop-up shade and any hat without a cord.
Wear what you can sit in all day: most vantage points do not let you back in once you leave. On published hours, Mrs Macquaries Point opens at 10am and closes at 12:30am with no sunshades; the Opera House Forecourt admits free ticket holders between noon and 3pm, also without sunshades; Observatory Hill opens at 2pm, and shades come down at sunset. City of Sydney's guide says: "Pack sunscreen, a hat, water, snacks, wet weather gear and a blanket to sit on." Long linen sleeves, a corded brim, a dress for the 9pm and midnight shows and a small bag cover the rest.
Late December if you are coming for the harbour, early December if you want the beaches in term time. NSW schools finish on Thursday 17 December and the summer holidays start the next day. The Salvation Army's Carols in The Domain runs on Saturday 19 December from 1pm to 11pm, and its Phillip Precinct site returns to the public on the 22nd. Christmas Day is a Friday. Boxing Day brings the Sydney to Hobart start at 1pm and, on the listing's published pattern, the 10am release of free Opera House Forecourt tickets for New Year's Eve. Monday 28 December is an extra public holiday.
A degree and a half warmer by day and nearly two at night. NOAA's Observatory Hill figures give December 26°C / 79°F and 18°C / 64°F, against November's 24°C / 75°F and 17°C / 63°F, with about one fewer rain day. You gain half an hour of daylight; sunset passes 8pm from mid-month. The 3pm wind is a notch stronger, 19.5 km/h against 19.4 on the Bureau of Meteorology's record. The bigger change is the calendar: NSW schools break up on 17 December, and the month ends in Christmas, Boxing Day and New Year's Eve. Our November guide covers storms and UV.
Swimwear first, and Sydney has the history for it. The Australian National Maritime Museum traces Speedo to MacRae Knitting Mills, formed in 1914 with its first factory on Regent Street, which launched swimwear under the Speedo name in 1929. Seafolly was born on Bondi Beach in 1975 and still builds its suits around fit. For a harbour dinner on 31 December, Carla Zampatti, who launched her label in 1965 while the Opera House was still under construction and opened her first Surry Hills boutique in 1972, sells an evening and party range. Over the swimwear goes linen with sleeves, and flat sandals.