Packing for a two-week winter trip in a carryon

Is it possible to pack for a trip up north during winter in a single suitcase? Reader S. asks….1-191-14-1

I saw your blog and decided to ask for your help. Hopefully you will respond before I depart warm Florida for my business trip to Boston leaving mid-January 2015. My job assignment will be from January to August. Here’s my dilemma, I will be staying in a hotel weekly and commuting daily to work using public transportation in Boston. I’m a Southerner so I don’t have a true four season wardrobe.

#1 I’m having trouble trying to decide how to dress while commuting to work in the winter weather and to not overdress in too many layers. I do not have an office or a dedicated area to store my belongings, so I have to keep my things with me at all times. I heard other say they have a jacket or shoes they keep at work so they only have to dress for the commute.

#2 Trying to pack for two weeks while the employer will only pay for one piece of luggage. No luggage overage charges will be reimbursed. Winter clothes weigh more and take up more space. Can’t decide between slacks, blouse and a jacket or dresses and a jacket.

Any suggestions would be greatly appreciated.

Wow. That is a lot of complicating factors! Let’s take them one at a time.

First, the commute. There are three critical things you need for commuting in winter—a great coat, a pair of waterproof boots, and silk underwear.

  1. The coat. When I travel north this time of year I always bring my black puffy coat.Glamorous, no, but it is super warm.
  2. The boots. I really like La Canadienne boots. They are waterproof and designed for comfortable walking in super cold temps. Of course they are pretty pricey. A less pretty option (but just as warm) is a pair of Sorrel boots. On days you don’t want to wear them all day bring shoes to change into and a collapsible tote bag to hold your boots.
  3. Long underwear. The other important thing you need is silk long underwear, both leggings and shirt. It’s great because you can wear it under everything, it will keep you warm outside, but you won’t overheat once you go inside.

You can keep your coat and the tote bag with your boots in it with you at your desk.

Second, outfit planning. Find out if your employer will cover laundry service since you’ll be gone for longer than a week—I know many employers will pay for dry cleaning if you are gone for a certain amount of time.

When planning what clothes to bring, make sure you choose items that you can layer. Sweaters over button downs over your silk underwear, etc. If you wear a dress bring a sweater to wear over it and wear the silk underwear under your tights and boots. Another tip to remember: two thin items will keep you just as warm as a thicker one (especially when adding silk underwear!) but will take up far less room. So avoid your heavy sweaters, even though it feels natural to pack them.

Here is a post I wrote last year with a two-week packing list for a winter trip. (If you have to wear suits, here is a post from Outfit Posts with suggestions on how to wear a suit during crazy-cold temperatures.)

The third, and final thing to consider, is how to pack it all in one bag. It is certainly possible to fit all of this into a carryon, as long as you wear your boots and coat on the plane and utilize a few packing tricks.

  • Packing cubes. I know I talk about them all the time, but they are so useful! I can compress a week’s worth of clothes into one packing cube.
  • A trick a reader suggested to me before a two-week conference a few years ago: fill up your travel containers with your normal shower products (shampoo, conditioner, facewash, bodywash, etc) and see how long they last you. Mine lasted me far longer than the two weeks I would have needed, so I knew there was no reason to pack more toiletries. However, if you need larger quantities it may make sense to buy some of your products at your destination. If you are staying at the same hotel each trip see if you can leave a few things there between visits.
  • It’s not always easy, but even for longer trips I recommend bringing only three pairs of shoes, including the pair you wear during travel. Shoes take up a lot of room and weigh a lot, so be very deliberate about every extra pair you bring!

Even if your boss will pay for you to check a bag I would still try to carryon. There are just too many variables when you check a bag, especially with winter weather delays and flight cancellations.

It will take a lot of planning, but it is definitely possible to carryon for two weeks in the winter. Good luck!

Readers, do you have any tips for Reader S?

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  1. If you’re staying at the hotel, you MAY be able to negotiate a long-term rate that’s cheaper than weekly stays AND allow you to keep things in the hotel room when you fly home on the weekends (clothing, etc.). That’s also a good time to take advantage of a local laundry service (NOT hotel laundry). If not, the bell desk at the hotel would likely keep a bag for you, so you could shuttle things up/back as you need them (ramp up, ramp down in terms of volume).

    Overall, though, you shouldn’t need much, and it might be easier to pack less and budget for buying items you need in Boston (foundation pieces, etc.).

  2. I am from the Boston area and worked in downtown Boston for years. Know this – besides the cold, it is very windy in Boston. I once read that it is windier than the “Windy City” (Chicago). So… in addition to a puffy coat and really warm waterproof boots, make sure to have a hat, scarf and mittens (yes mittens, much warmer than gloves.) Umbrellas are often useless because of the wind. (The rain and snow come at you sideways and the umbrella goes inside out.) Most veterans of Boston (and NY) DO NOT CARE what they look like when they are outside. For ex, nice leather boots with heels are useless in the slush and on ice, and if space is at a premium, don’t bother with them.

    I second the suggestions of buying toiletries up there and finding a way to stash some stuff over the weekends. When I commuted back and forth (one year), I kept a toiletry bag in my desk drawer – see if you can find a place to do that. I agree completely on the silk underwear, and on the suggestion to drop off your dry cleaning/laundry for weekend service.

  3. I would plan on buying a couple heavier layering pieces that in Boston. Plan on shipping or taking home on the plane part of the winter clothes in April. So you can bring back spring clothes. You might want to buy your winter boots in Boston when you get there. They should be on a clearance sale now. Another idea is flannel lined leggings that can be worn with dresses or under work pants. You can buy these two for ten at Walgreen’s. Put a heavy wool sock on with them and your cute dressy boots and they should be perfect for the office.

  4. Hmm, I’m from Boston as well and I’m not sure that I agree about the need for silk underwear for work. Its fine to bring them, or buy them in Boston, but most offices in Boston are not any colder than any where else. If she is commuting by train, those can also be hot and stuffy. Depending on where the hotel and office is in relation to the means of transportation, she may only need to walk a few blocks at most in either direction, and wearing silk underwear all day in an office could be overkill. Or, if commuting by car, those are heated! I would second the warm coat, boots (if snowy or rainy), hat, gloves, scarf recommendations.

  5. Forget silk thermals. Merino wool is the way to go. Less sweat uptake, so you can wear it multiple days without washing it. Particularly in shirts I think it’s the ideal fabric for travel.

  6. I’m a little confused – the OP states “the employer will only pay for one piece of luggage”. I read this as she’s allowed a piece of checked luggage?

    If so, it’s no big deal to travel for two weeks with checked luggage even in a cold climate (wear your coat and boots onto the plane!). Though you will need a laundry service.

    Also, if you are staying long-term, find an apartment hotel and negotiate a long-term rate with them. I guarantee you it will be cheaper than staying in a business hotel five nights a week. Plus there are several advantages to apartment hotels:
    1) almost all have free guest laundry facilities in-room (at least in this country, especially Oaks apartments)
    2) you can cook in your room, which means not relying on restaurant food all the time (because if you eat in restaurants every night, not only will it get tedious, but you will gain weight)
    3) if you rent one apartment long-term, you can leave your stuff there on the weekends.
    4) they’re usually serviced by cleaners every other day or at least once per week, so that’s something you won’t have to worry about (and also something you can negotiate about for a cheaper rate – you don’t need your room cleaned daily, weekly is enough for example, you might only choose fresh towels twice weekly and linens once per week)

    If you are not in control of where you are staying, I suggest you find a way to change that. Eight months is a long time to stay somewhere inconvenient or inadequate.

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