What to Wear in Key West in December

Pack for two parades after dark. NOAA NCEI's normals for Key West International Airport give December a 25.4°C afternoon and a night that falls to 68.3°F (20.2°C). The hourly normal at 8pm, when the Lighted Boat Parade sails into the Key West Bight on Saturday 12 December, is 71.5°F. Schooner Wharf Bar, which runs the parade, sets the tone: "Look for palm trees - not spruce, fir or pine - aboard the holiday vessels." Nineteen nights later the town stands on Duval Street for midnight, and in 2025 a lighted conch shell dropped onto Sloppy Joe's roof. Both nights mean hours on your feet, so build the trip around one navy cardigan and closed shoes.

The capsule

1. 
   01

   Navy fine-knit cardigan, crew neck

   For the Harbor Walk. The parade party starts at 6pm and the boats arrive at 8pm, when NOAA's hourly normal is 71.5°F: mild, until you have stood beside the water for two hours. An average December also brings 4 nights at or below 60°F. Buttoned, it goes over the lime tank on parade night; open, it goes over the print shift on New Year's Eve.

2. 
   02

   Lime-green ribbed tank, racer cut

   Afternoons still reach 25.4°C on NOAA's normals, warm enough to walk Old Town in a tank. A fine rib lies flat under the cardigan, with no sleeves to bunch at the elbow, and the racer cut looks finished when the cardigan comes off. Lime against white and navy is also easy for your group to find on a dark, crowded harbour front.

3. 
   03

   Pink linen tie-front shirt

   For a day on the water. The Key West "Bight" Before Christmas calendar lists Cocoa and Carols cruises on Schooner America 2.0 from 19 to 24 December and a Christmas Day brunch sail from 10am to 12:30pm. Long sleeves keep the sun off your arms on deck, the knot at the hem sits above the trousers, and it layers over the tank ashore.

4. 
   04

   White cropped cotton-twill trousers

   Parade night means two hours on the Harbor Walk, some of it perched on a bench or a dock edge. Pressed cotton twill gets up from that without the creases linen takes, and a crop above the ankle keeps the hem off wet boards. White catches the boat lights after the mid-month sunset at 5:41pm and goes with every top in this capsule.

5. 
   05

   Pink-and-green floral-print shift, sleeveless

   Lilly Pulitzer's shifts wore Key West prints. Cooper Hewitt credits Key West Hand Print Fabrics with every one of Pulitzer's prints from 1962 to 1985, most drawn by Suzie Zuzek. On New Year's Eve a shift has no waistband to bind through hours on your feet on Duval Street, sleeveless suits a packed crowd, and the navy cardigan goes over it for the walk home.

6. 
   06

   White leather deck shoes

   At midnight on New Year's Eve, Keys Weekly reported in 2025, "crowds pack Duval and Greene streets around Sloppy Joe’s". Closed leather toes come through that crowd where sandals do not, and laces keep the shoes on when the street carries you along. A deck shoe also does its first job on Schooner America 2.0, where a pale rubber sole grips a wet deck.

7. 
   07

   Dark brown woven leather sandals, buckled back strap

   For daytime in Old Town. Hemingway Home opens every day of the year, Christmas Day included, with tours every 15 minutes from 9:15am, and a woven upper breathes on a 25.4°C walk there. A buckled back strap keeps the sandal on in beach sand. For a pair made on the island, Kino Sandals has cut and glued leather sandals by hand since 1966.

8. 
   08

   Flamingo-pink mini crossbody

   Parade boats throw candy and beads to the crowd, and Schooner Wharf promises children "the chance to catch" them, so keep both hands free. A mini bag on a long strap holds a card, a phone and a room key, and its turn-lock flap stays shut in a crush. Flamingo pink picks up the pink in the shift and stands out against the navy cardigan.

A suggested look — lime green ribbed tank, navy crew-neck cardigan, white cropped cotton-twill trousers, white leather deck shoes.

What to avoid

• Alcohol or glass on a City beach — banned at any time
• Open sandals in the midnight crowd at Duval and Greene
• Choosing a drop site after 11:55pm
• Waiting for a car on a closed block of Duval
• Bare arms for two hours on the Harbor Walk after dark