Packing for 2 weeks: winter

A few weeks ago, I got an email from a reader.

I leave next Wednesday for my longest trip ever to Wisconsin for work. Its 10 days in Wisconsin! Thankfully I will be running from the hotel to the car and then the car to the warehouse. However, I can only bring one suitcase. Do you have any advice on how I should pack? I know you have done some 5 day trips but I can’t remember if you have done a 10 day one. Please help! I’m from Georgia and I’m not used to those temperatures!

Oh man. Ten days in Wisconsin is no joke for a southerner! Packing in one suitcase for ten days is hard enough in the springtime (like I did here), when you don’t have to worry about coats and boots and 9 degree weather. There are a few things to keep in mind to make it easier.

  1. Two thin layers take up less room than one thick layer.
  2. Plan to wear everything more than once.
  3. Wear your bulkiest items on the plane.
  4. Take commuting shoes (like these).
  5. Use packing cubes!

Keeping those tips in mind, here is a packing list for the dead of winter.

  • 3 pairs of work pants
  • 1 dress or skirt (or an additional pair of pants)
  • 1 casual pair of pants
  • 6-8 shirts/cardigans that can be mixed and matched
  • Jewelry/belts/scarves
  • 2 pairs of work shoes
  • 1 pair of commuting shoes (wear on the plane)

Here are the clothes to bring.

Two week winter packing

Here are some of the outfits you can make with the clothes. Obviously there are plenty more combinations!

two week winter packing outfits

Readers, any tips for people traveling for a long time in the winter?


  1. Wisconsin girl here (but currently spending several weeks working in Toronto – also cold). I love sweater tights – they’re warm and don’t take up much space in your bag. I prefer one pair of nice boots over two pair of ballet flats because in winter, even inside the buildings tend to be fairly cold (I’ve got a space heater under my desk during the winter). Also, don’t forget your hat and gloves. It’s all too easy to forget to toss them in your bag when it’s warm and get to the freezing airport with cold head and hands.

  2. For a woman or a man, can suggest that a turtleneck/mock turtleneck thin knit shirt is another good layer piece, and supplements the job done by a winter scarf in keeping the neck warm and cold air penetrating the neck closure of your coat. Also, a thin cashmere sweater is another really good layering piece.
    Finally, a good quality down vest is very useful, and can be ‘squished’ for efficient packing, then fluffed up again before wearing it.

  3. Just ship a box of stuff by UPS. It really is not that expensive if you stick to standard ground service. There are many ways to ship UPS or other carrier, perhaps your place of work at either end already has an account.

  4. I second the Cuddle Duds – I’ve spent time on business in Toronto, Boston, etc. and they seriously are a light layer to help you really stay warm. I’m currently on an 11 day run with a combination of two warm cities and one cold. I packed a neutral suit and a few pairs of pants with several mix and match tops and it has worked out nicely. Thanks for your blog – it’s always fun to hear how others are doing travel.

  5. Great tips! I’m sitting in the airport right now wearing three layers of shirts to save on space in my carryon. The one thing that wasn’t included in your run-down was pajamas. I usually pack shorts and a t-shirt even in a cold climate, and just crank the heat in my hotel room.

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