What to Wear on a Winter Trip- For Her

Today I’m sharing some ideas for what to pack for a winter trip.

While we were in Ireland a couple of weeks ago, Tyler and I decided on a whim to use some airline points to fly my little sister Miriam out to meet us in England for the remainder of our trip. She had never been abroad, and we were SO excited to show her the ropes.

With less than 24 hours’ notice before she needed to check in at LAX, Miriam frantically texted me and asked me exactly what she needed to wear on the trip. I started writing this lengthy text about what she needed to bring to wear and quickly decided to transfer it to a Google doc to use for a blog post later.

While packing for a long trip is tricky, Tyler and I have managed to get a grip on what works best for us over the last few years. Today I am going to talk about my winter travel wardrobe, and Tyler is going to post about his soon, too.

A few things to note first.

This isn’t a “packing light guide,” alright? I’m not really the type of person that gets a huge sense of pride from rolling around a little baby carryon for a two-week trip, ESPECIALLY in the winter when the clothes take up twice as much room. I’m more of a pack-what-you-need-and-what-you’ll-wear gal, and for longer trips I always check a bag (sue me).

I suggest staging your wardrobe before packing it into your suitcase. After you lay everything out on your bed, take a deep breath, a sip of water, and a quick walk around the house. Then, come back with a fresh set of eyes, picture the itinerary for your trip, and ask yourself “am I REALLY going to wear this?” about each item you’ve laid out. I still end up regretting one or two frivolous items that stayed in the bottom of my suitcase the whole trip, but I am getting better and better at narrowing my wardrobe down.  

I’d also like to take this time to announce that Tyler and I are officially Packing Cubes People. We are here today to tell you that your Aunt Sue was right: packing cubes really are the way to go. In preparation for this this last trip, we each bought a set of five on Amazon. Fitting our clothes into the cubes allowed us to stay organized throughout the trip. Tyler and I have a truly special gift of turning hotel rooms into a complete disaster within minutes. With the packing cubes, however, we were able to not only keep our act together a bit more, but also packing up between cities was MUCH easier.

With that, I’ll get to the breakdown of what I bring to wear on winter trips.

Footwear

Sturdy boots: I’ve learned this lesson the hard way a few too many times. With winter weather, you just cannot mess around with flimsy footwear. I suggest bringing one VERY sturdy pair of boots that will last the entire day, or trip for that matter, in any weather. These will likely be your everyday choice while you are exploring, so make sure they are comfortable and that you can easily put those 15,000 steps on them each day. I recently invested in these Timberlands and stomped all over Ireland and England in them without a care in the world. 

Cute Booties: You’ll also want to bring one pair of dressier boots or booties to wear when the work boots just don’t cut it. I wore my heeled booties to afternoon tea, a couple of dinners, and the night we attempted to see Book of Mormon on the West End (long story, will talk about it here later but Google “Oxford Circus incident” for now). It’s nice to have a way to dress up a couple of times throughout the trip. Note: these booties should still be comfortable enough to walk for a couple of hours. 

Comfortable Sneakers: These don’t get as much use in the colder weather, but I still wear a pair of Nikes on travel days. They are much easier to pull off in the security line and are more comfortable on a day spent hopping in and out of trains or rental cars. I also like to have these on hand on the off-chance that we make it to the hotel gym (rarely ever on vacation travel, a few times a week during work travel).

Outerwear

Puffy Jacket: I tried to avoid the snowman look as long as possible, but there’s nothing worse than shivering your way through a city when the temperature drops below 40 degrees. I love this packable puffer from Free People because it’s easy to layer over and under sweaters and thicker coats:

Wool Blend or Pea Coat: Same idea as the cute booties. For days when you want to class it up a bit or nights that call for something dressier than a ginormous puff jacket, bring along a wool blend or pea coat of sorts. Make sure this layer is still warm enough to wear on cold winter nights. 

(Optional) Leather Jacket: I love a good leather jacket. Surprisingly warm and considerably less obnoxious than the aforementioned parka, I love to bring one of these along to wear on sunnier days. Granted, the forecast for this most recent trip included a handful of days in the high 50’s, so I ended up layering this over a chunky sweater several times. For trips in the colder months of January and February, you might want to leave this jacket at home.

Pants

Jeans: The number of pairs of jeans you pack depends on how long you can stand wearing jeans without washing them. I won’t get specific about my tolerance, but I usually pack three or four pairs with me for longer trips. We sometimes try to do one load of laundry if we get an Airbnb with a washer/dryer, but it’s a big hassle, and we only do so if absolutely necessary. I typically pack two or three denim pairs and one nicer pair of black jeans to wear with blouses or sweaters for dinners and such.

Leggings: Again, tolerance preference here. I always wear a pair of leggings on the flight, save one clean pair for the end of the trip, and then bring one or two extras to wear throughout the trip. So 3-4. My favorite, favorite leggings for travel and life are the Lululemon Align leggings. 

Sweats: I used to not bring sweats on winter trips in an effort to save space, but I quickly grew tired of being cold in hotels and Airbnbs. Also, the sweatpants that I used to wear nightly would commandeer about half of my suitcase. Last Christmas, my mother-in-law revealed that she had been judging my loungewear for years (what is so wrong about a stolen pair of men’s size large Nike sweats and a green Cal Poly sweatshirt??) and presented me with a lightweight but perfectly cozy pair of Lululemon joggers. These fold easily into my suitcase and are so nice to wear to sleep in and while getting ready on those chilly mornings. I never travel without them now.

Tops, Sweaters, Etc.

Sweaters: My winter travel look is very simple: jeans, boots, and a warm coat layered over a pullover sweater. It’s comfortable and easier than messing around with multiple layers. For longer trips, I usually pack anywhere from 5-7 sweaters or warmer long-sleeve tops. I’m a shameless outfit repeater, so I’ll wear each a couple of times throughout the trip. I do suggest bringing ONE cozy cardigan to wear on the plane and in the hotel room– I’m obsessed with mine from Barefoot Dreams.

Bodysuits: Bodysuits are so versatile, so I love packing 1-2 in my suitcase. I can dress them up for a nice dinner and booties or wear them underneath a sweater for added warmth.

Socks + Underwear

How many times have I said to myself, usually in the dead of night in a last minute packing frenzy, “Oh, we’ll definitely do laundry halfway through, so I’m only going to bring X pairs of socks and underwear”? Spoiler alert: WE DIDN’T DO LAUNDRY. Even if our Airbnb says it has a washer/dryer, I ALWAYS bring enough socks and undies for every single day of the trip plus 2-3 extra.

Accessories

Depending on the amount of space left in your suitcase (and if you’re me, how many books you’re planning to buy on the trip), you might want to bring a couple of scarves and/or beanies to wear on colder days. I also love a beanie for day 4/5 of unwashed hair. For this last trip, I brought one of each and just planned on buying more if I needed them.

All this being said, there’s really no need to overpack. You can always buy more clothes if you are desperate. H&M and Zara are easier to find than public bathrooms in Europe, and I’ve been known to make a blitz trip into either one if I’m ever in a pinch.

Check out more of our travel tips and tricks here.

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