What to Wear in Key West in January

January in Key West belongs to poetry. The 44th Key West Literary Seminar runs 7–10 January 2027, and its organisers write that "Thirty-four years ago we focused on poetry with a visionary gathering dedicated to the life and work of Elizabeth Bishop". In 2026 every session ran at the San Carlos Institute, 516 Duval Street, one after another, so you sit indoors most of four days. NOAA NCEI's airport normals give a 24.3°C afternoon and a night that falls to 65.5°F (18.6°C), and on 15 January 2026 NWS Key West forecast northwest winds of 25 to 30 mph behind a cold front. Pack a denim shirt and a pink knit for the hall, and an oatmeal sweater for dinner outside.

The capsule

1. 
   01

   Light-wash denim shirt, worn open

   Your layer for the street. Sessions run back to back at the San Carlos Institute, so the walk along Duval is the only weather you meet. Behind the front of 15 January 2026, NWS Key West forecast northwest winds of 25 to 30 mph, with gusts near 40. Worn open over the pink knit, denim blocks that wind at noon and comes off indoors.

2. 
   02

   Shell-pink short-sleeve cardigan

   Buttoned to the neck, a short-sleeve cardigan works as a top: neat enough for a seminar hall and cool enough for NOAA's 24.3°C afternoon on the walk to lunch. Shell pink sits quietly under light-wash denim and over black trousers. A ribbed hem stays put when you sit, so the knit looks the same at the last session of the day as at the first.

3. 
   03

   Oatmeal crew-neck sweater

   For the night a front comes through. An average January brings 7.3 nights at or below 60°F and 1.1 at or below 50°F, and NWS Key West's brief of 29 January 2026 told the Keys to "Prepare for the coldest temperatures thus far this winter season". Oatmeal goes over the lace dress at an outdoor table and over the pink cardigan walking back.

4. 
   04

   Black pleated trousers, cropped

   Seminar sessions run consecutively in one hall from Thursday to Sunday, and a pleated front gives you room to sit through every one. Black takes the shell-pink cardigan by day and the oatmeal sweater at night. A crop at the ankle shows the laced derbies and clears a wet kerb when the rain that runs ahead of a cold front comes through.

5. 
   05

   Black cotton-lace midi dress, short sleeves

   Seminar registration includes the opening-night reception, catered with an open bar, and this is the dress for it. Cotton guipure has weight without heat, sheer lace sleeves cover your shoulders, and a tiered skirt sits well in a row of seats if you go straight on to an evening session. At 6pm NOAA's hourly normal is 70.5°F; the oatmeal sweater waits in the tote.

6. 
   06

   Black leather derbies

   Most of this week happens on foot: hotel to the San Carlos at 516 Duval, out for lunch, back for the afternoon, then dinner. Laced black leather stays on and stays smart throughout, and keeps your feet warm on one of January's 7 nights at or below 60°F, where sandals do not. A thin sole crosses a hall quietly during a reading.

7. 
   07

   Natural straw boater, sky-blue band

   For the lunch walk on Duval and an hour in the Elizabeth Bishop House garden, open weekdays from 10am to 3pm, the seminar's Thursday and Friday included. A flat brim shades your face on a 24.3°C afternoon, and the sky-blue band picks up the denim. Leave it at the hotel on a front day, when a 25 mph wind takes a boater straight off.

8. 
   08

   Stone canvas zip tote

   You leave in the morning and return after dark, so the bag carries the day: a notebook, the oatmeal sweater for the evening, the denim shirt once it comes off. A zip top keeps it all in under a seat. At Key West Food & Wine, 27 to 31 January, the photo ID the 21-and-over festival asks for goes in the front pocket.

A suggested look — shell pink short-sleeve cardigan, light-wash denim shirt, black pleated cropped trousers, black leather derby shoes.

What to avoid

• A boat trip the day after a cold front
• A straw hat in a 25 mph northwest wind
• Key West Food & Wine without photo ID — 21-and-over only
• A room booked late for seminar week
• Bare arms at an outdoor dinner on a 60°F night