Dressing Tips for Winter Travel
Winter travel presents a unique set of challenges! Whether you’re heading to a snowy destination or escaping to warmer climates, being prepared is key. Today, I’m sharing some practical tips on dressing for winter travel, especially when it involves flying to a destination with different weather.
If you have any upcoming travel plans, you might also enjoy reading these posts:
Dressing for Winter Travel
Understanding Your Destination’s Weather
Before you start packing, it’s key to understand the weather conditions of your destination. That may seem obvious, but it can easily be overlooked, especially if you’ve traveled there before. I neglected to check the forecast for my trip to Austin but had luckily packed a large cashmere wrap, which did double duty to keep me warm.
A quick search online for the latest weather forecasts can give you a clear idea of what to expect. Look for information on temperature ranges, precipitation, and any weather advisories.
Dressing for the Journey
When traveling during winter, dressing in layers is your best bet. The airport and airplane temperatures can be drastically different this time of year. Plus, think about all of the walking and movement you’ll be doing once you get to the airport…checking in, security, boarding, etc. I always carry at least one cashmere wrap and love the color options of this oversized one from J. Crew.
BTW- I never recommend loose, wide-leg pants for airline travel because, while comfy, they’re hard to keep off the floor when using the facilities. I also choose to wear a mask aboard flights these days. You choose what works for your health considerations.
- Start with a lightweight, moisture-wicking base layer or shirt to keep you dry.
- Choose clothing that’s comfortable for long flights and easy to remove or add as needed. I love brands like Eileen Fisher, Athleta, and Quince.
- Shoes should be easy to slip on and off (if you don’t have TSA pre-check) for airport security. I like to wear my casual sneakers or tennis shoes, which you can find in this post. Also, be aware that depending on the airport, they may ask you to take your boots off if you wear them!
- I love to have a cashmere scarf/wrap in my bag, just in case. It’s lightweight and easy to throw in your bag and has rescued me during many a frigid flight.
Packing for a Winter Getaway
Packing light yet sufficiently for winter travel can seem daunting. With many winter trips under my belt, I feel like I’m getting to be a pro at this one. I’ve learned to focus on bringing versatile pieces that can be mixed and matched, as well as a wide variety of layering pieces.
Remember, heavy winter coats and boots take up a lot of space, so wear your bulkiest items on the plane. If you need to pack big and bulky items like snow pants, consider compression bags to save space in your luggage.
I always recommend investing in a sturdy suitcase that’s easy to maneuver. I upgraded to a four-wheel roller bag several years ago and felt like someone had flipped a duh switch! Why had I been struggling with two wheels when four pivoting ones made life so much easier? I love my Away carry-on, but this one is my favorite because it’s tiny and has a spot for my laptop. You can read about more great options here.
Navigating Airports and Flights
Airports and flights can be challenging during the winter. Dress comfortably and be prepared for potential weather delays. Many people love to carry a small travel pillow, an eye mask, and earplugs to help them relax on the flight. Keep important documents and medications in your carry-on, along with a change of clothes in case your luggage is delayed. I stopped checking a bag years ago, so I typically have everything I could possibly need in my carry-on. You can see my toiletry packing list here.
I always carry my passport, phone, and other critical documents on my person in a waist bag. It makes them quick and easy to access and impossible to lose. This little convertible one comes in lots of colors.
Arriving in Warmer Weather
If your destination is warmer, plan for a smooth transition. Pack clothes that can be layered down, like lightweight jackets and removable liners. Upon arrival, you may want to change into lighter clothing, so keep an easily accessible outfit in your carry-on. This approach ensures comfort without the hassle of rummaging through your luggage at the airport.
It’s never fun returning from somewhere warm and sunny and walking out of the airport into a frozen tundra. Plan accordingly, and have something warm to layer on when you fly home.
Smart Packing Extras
Beyond clothing, there are a few extra considerations for winter travel. Travel insurance is a smart idea, especially with all of the sickness and craziness happening today. It’s also wise to keep a list of emergency contacts and any necessary health precautions. Lastly, pack a few often-forgotten items like lip balm, sunscreen, and moisturizer to combat dry, cold weather. Remember, the goal of any trip is to create memorable experiences, so dress smart, pack right, and make the most of your winter adventure!
Do you have any upcoming trips planned? What tips do you have that helps make your travel seamless?
Hi Jennifer,
We are getting ready to leave for HI on Tuesday morning, for our move there. We’ll be leaving with both of our dogs, two bags, and our carry ones from SEATAC. I have to wear winter clothes, and have summer stuff packed in our cases. We are going nuts right now, lol!!
Good Luck Linda!! You’re off on quite an adventure.
I haven’t traveled with just a carry-on for years since the last time that I was unable to lift it up and had to ask for help. Kind of embarrassing. Your Monos bag looks super nice though. I love my Lo and Sons Pearl handbags. They’re just the right size for carrying a small wallet, cellphone, sunglasses, and lipstick and the Saffiano leather is so durable. Your post makes me want to go on a trip! Thanks for all you do!
I love my Lo & Sons Pearl bag too!! It’s really perfect for travel.
I’ve started bringing my own (empty) reusable water bottle to avoid having to buy plastic. Most airports have water fountains that allow for easy filling up.
I love your traveling tips..you always have such practical advice! I have a small Dakine backpack – actually kids proportions – that I purchased for a physically active trip years ago. I have used it a lot since. I’m 5′ and it’s perfect to carry my iPad and other essentials on the plane (my husband carries a normal sized backpack). It’s perfect to take on day trips & sightseeing We find that we can usually fit everything in a carry on suitcase and our packs – especially for warm climates. I’ve gotten lots of inquires and comments when I use it!
That sounds like a great idea. Backpacks are perfect for hands free travel.
I don’t know why but the last email link I received was 1/9/24 and then nothing. Don’t know if I somehow unsubscribed? I just resubscribed so we’ll see. Just wondering if the email links are no longer being sent
Hi Diane. There was some sort of snafu in my mail delivery on Jan 9 and we’re still working to fix it. Thanks for your patience.
I should add that I also try to book early flights. They are less likely to be cancelled or delayed. I rise early enough to shower and enjoy a coffee before leaving home. Not being rushed starts my day off calm.
I agree but I try to avoid the crack of dawn flights because I’m slow to start in the am.
I’m a morning person, so it works for me but it would probably just stress you. I don’t mind getting up at 4 (prefer 5) to start my day. I like the quiet in the morning with just my sleeping dog and morning coffee.
When leaving Vancouver for Ottawa in the winter I pack my puffer, gloves, boots & hat on top of my checked luggage so as soon as I receive I can easily pull them out and put on before stepping out into the cold. I don’t like to travel with heavy, warm garb on planes or through airports. When travelling to a warm destination, I wear light clothes and have a summer outfit in my carryon to change into before leaving the airport.
I always pack my meds, headphones, book, iPad, a bra & panties, a bathing suit, and a change of clothes in my bag to make sure they are with me when I get to my destination. Fortunately, I have never lost my luggage and I have travelled a lot over the years. I just can not travel with carry on only. I like variety and don’t want to have a suitcase, no matter how small, when going through airports. In stead, I opt for a leather backpack. Hands free at all times.
That sounds like a great way to go. You’ve been very lucky not to have a bag lost!
Hello Jennifer, great tips, I love your travel posts! I have a more personal question – I notice in one photo you show your Canadian and your US passports. So do you use the Canadian one for entering Canada and the US one for returning? This doesn’t cause any problems? Or are you supposed to do that? I, too, have two passports, British and Canadian, but I just use the Canadian one when travelling to the UK since my husband only has a CDN passport and we like to go through immigration etc. together.
As a US resident, I’m required to travel under my US passport but I always carry my Canadian. If one gets lost, I never want to be trapped in a foreign country. Ditto about traveling with my husband because he’s not Canadian.
Do you have one of those masks with a hole for a straw? I haven’t been able to get my head around airline travel beyond more than an hour or so, without the ability to drink. Breathing the recycled air makes me reluctant to travel by air at all.
I just slip it off one ear to eat or drink quickly. I just feel better wearing one in a stuffy plane.
Great post! You always look so stylish and put together while traveling! You also look comfortable and that’s so important too.
Comfort is key which is why I seldom fly in jeans.
I always take a scarf but like your idea of a cashmere wrap. I think we should all take water bottles as our adult children do. In fact, to me, buying a water bottle is a sign of age. Look for a bag that has a pocket for one.
Interesting point! My refillable water bottle is a heavy metal one so I’ll need a lighter option.
Great post! Thanks for the tip about not wearing loose, wide-leg pants when flying. Had never considered that point before (yuck!).
One thing I always do when flying (regardless of time of year) is to put some Vicks VapoRub in an old contact lens case and keep that in my purse, in case I’m seated near someone eating stinky food or emitting godawful body odor (it’s happened before, making a long flight seem even longer ….). Just a discreet dab in both nostrils blocks out all smells.
Great idea! I could have used that in my last flight. Someone blasted out the restroom and the smell was so bad the flight attendant finally broke out some room spray. It was awful!!
Vicks, Carmex or vaseline just inside your nostrils also prevents germs from easily entering your nose and causing havoc with your immune system.
Great to know! Thank you
Hi Jennifer,
Loved your article about flying and what to take. I have found that international flights tend to be more comfortable than long domestic flights. Even in economy on international flights I have been provided with a fresh blanket. In addition, except for Icelandic air, there is a screen with multiple movies, TV programs, and music. Some airlines even had games. Flying coast to coast with a midway stop usually doesn’t have the blanket and I find I need a wrap. It is on this type of flight that the seat holder for a cell really comes in handy, since typically there is no screen for entertainment. My last comment is about neck pillows. I have found the inflatable, flocked type of neck pillow to be the most comfortable and less of a hassle. I can blow it up to just the right size for me and once I arrive I deflate it and it packs flat. Thank you for your great articles. Nan Sullivan
I love the idea of a deflatable one. It would stay cleaner inside your bag while going through the airport than a solid one hanging outside.
No huge travel plans but all of your advice is well taken! I like your Away luggage and may look into it! There’s always next year! Thanks Jennifer and bon voyage!
Paulette: Before you buy Away luggage have a look at the Monos (the one Jennifer says she prefers). I have a couple of sizes of Monos and LOVE them. Monos has received some very good recommendations from sites that evaluate such things as luggage (for business and vacations) and Monos comes out on top! The Monos bag called Weekender and their Backpack both have sleeves to fit over your suitcase handle and are well designed.
And…if you want a cross body bag that carries those things that you want right with you and handy go have a look at Poppy Barley….started by 2 sisters from Edmonton and they have all their products made in factories in Mexico that are run by women! poppybarley.com