How To: Plan & Pack Winter Clothes in a Carry On

(If all went as planned) I am currently in Iceland, enjoying my 30th birthday gift to myself. We're attempting a v. ambitious Ring Road trip in seven days; I'm confident we can do it. This is the first trip ever that I've taken to a chilly destination where I need legitimate winter clothing. The closest I've ever gotten to a chilly trip was when I went to Europe in January/February after I graduated school but that was pretty mild because we were in the UK, France, and Italy where it really doesn't snow all that much (though we did experience a freak snowstorm in London the day before our departure because that's just how the universe works).

I haven't ever had to pack loads of bulky, chunky knits and at first I was a bit apprehensive. But then, I realized it was kind of great because I realized I didn't have to pack as many pieces. Unlike tropical, humid, sunshiny destinations, I didn't need a new outfit for each day because I wasn't going to instantly dirty up my clothing with copious amounts of sweat and seawater. Visiting cold destinations means wearing coats constantly so you're going to look virtually the same in every photo anyway; does it really matter what you're wearing underneath? (Unless you're one of those fashion bloggers that get comped trips and you like to travel with giant luggage filled with a thousand outfits, in which case, it probably does matter what you're wearing underneath and you'd probably pack twelve coats. But fortunately, I do not fall into that category; carry on only, bitches!)
So, my strategy for this trip was to pack layers and do a bit of mixing and matching to optimize my minimal wardrobe. I wanted to use my tiny new roller (that I am in love with) and I wanted to pack efficiently but accessibly since we're road tripping. Because we're staying in a new town every night, I didn't want to have to mess up my entire bag every evening to get the items I needed. I mean, I can appreciate those crazy packing strategies people come up with - like stuffing socks inside shoes and saving small items for last so you can cram them into nooks and crannies - but those methods just aren't practical for this trip because then repacking my bag would be way too cumbersome. And honestly, I really don't like those strategies in general because they're not elegant; it seems rather haphazard and probably makes it difficult to locate specific items. But at the same time, I had to be v. strategic because I needed to be able to stuff everything I needed into my tiny bag.

This post is all about how I packed for 9 days abroad in a wintry destination with just an underseat carry on.

Mixing and matching is the main game plan for a winter holiday wardrobe so it's good to pick a theme so that your wardrobe offers you many possibilities. I don't think a color scheme has to be as limited as sticking to neutrals or going completely monochromatic; it could be prints or neons or pastels. Choose a style that suits you and that you're comfortable with.
Instead of choosing a color scheme, I think it's better to choose a style (this is true for packing in general), whether it's French girl chic (think bardot tops, breton stripes, and red lipstick) or bohemian hippie (crocheting, drapey silhouettes, headbands) and build a wardrobe around specific inspiration. For this trip, my theme is inspired by the All-American lumberjack so I'm packing plaids and earthtones, like olive, brown, grey, etc. To keep things from looking costumey, I'm also throwing in a few fun accessories in feminine pastels.

This is an obvious tip, but layering is going to be your best friend when it comes to facing low temperatures. It's going to be a better friend to you than your coat. But layering isn't just a practical measure; it's also an opportunity to build totally different outfits with the limited number of pieces you've packed. That's why it's important to pack a v. purposeful collection of clothing and know exactly how to mix and match the pieces.
Base Layer
The base layer is the most important, in my opinion, because it's the one you should use to keep you nice and snug. My base layer always consists of three items (on top of underwear): a tee or tank, a thermal top, and cozy leggings (I really like fleece-lined leggings and base layers from Uniqlo's Heattech range). The tank top is just a habit I picked up from years of my mom lecturing me as we bundled up for ski trips, but I like it because it's just an added layer around my torso. Plus, the tank will soak up any sweat and allow you to re-wear your long-sleeved shirt over and over, guilt-free (and odor-free). After all, it's much easier to wash and dry a small tank top than it is to wash an entire suitcase of clothes, right?

Intermediate Layer
For me, this middle layer is usually a soft flannel or a turtleneck and a pair of trousers. This is the more presentable layer that you'll use to cover up your base layer, unless you don't mind showing off your long johns.
Top Layer
It's really important to protect your core in order to maintain warmth; when it's chilly, your body works hard to pump blood to your vital organs, conveniently housed in your torso. (Interesting fact: that's why frostbite happens; your body is busy taking care of your vital organs so it just stops pumping blood to the lesser important extremities.) So, I like to add just one more layer to insulate my core. This layer is usually a knit sweater, fleece, or hoodie.

And of course, you need to top it all off with a good coat and anything to weatherproof yourself (like ski pants or a rain shell). If you're anything like me, you'll want a coat that's both practical and fashionable; the coat should be great at keeping you warm but also look stylish enough that you won't cringe when you look back at photos later on.

I like packable down jackets because they offer loads of warmth but take up little space. And for the weatherproofing, I suggest a nice rain shell and swishy rain pants (look for one that says "waterproof" or "water repellent" and avoid ones that say "water resistant" because that means rain will eventually soak through). I'm not a fan of lined shells because that just makes them bulkier, which is unnecessary; after all, we've got our base, intermediate, and top layer to keep us warm.

I've read mixed reactions on bringing rain pants to Iceland; some people say it's a necessity whereas others say it's just taking up valuable space in their luggage. Make your own judgment call.
The aforementioned items will keep your body warm, but you'll want some items to keep your head and hands and neck cozy too. That means packing gloves and/or mittens, hats, earmuffs, and scarves. That thing people say about losing half your body heat through your head is actually not true. But, that doesn't mean you don't lose heat through your exposed body parts. It's actually proportional so it's important to bundle up (e.g. if your head is 10% of your body and you were completely nude, you'd lose 10% of your body heat through your head and 90% through your body; get it?).

Plus, even if you've got expert mixing and matching skills with your under layers, your coat will be making repetitive appearances in all of your photographs. That is the other reason why accessories will be really key. You can pack a variety of hats and scarves and even sunglasses to mix up your daily vibe because these items don't take up much room.
It sucks when your feet get so cold that they turn numb and then it feels like you're walking around on useless brick feet. For Iceland (and as an investment for future cold weather occasions) I bought several pairs of socks from Uniqlo's Heattech range, which boasts socks with a normal thickness but provide extra warmth. It's important to choose socks that are breathable, because sweaty feet turn into smelly, uncomfortable feet. You also want your socks to be really warm so that you don't get frostbitten toes. But the most important thing is that your sock-covered feet fit comfortably in your shoes. If they're too tight, then there won't be enough blood circulation and your feet will get even colder. So, fight the instinct to layer socks and instead, wear one really decent pair.
I'm a firm believer that you never need more than three pairs of shoes on holiday and this trip is no different. I'm packing a pair of warm and weatherproof boots, a pair of sensible shoes, and a pair of sandals. The snow boots are for obvious reasons, the sensible shoes are for occasions where the boots are overkill and/or uncomfortable, and the sandals are for comfort and potential spa days (and in this case, for visiting the Blue Lagoon).
Packing Cubes
The key to packing winter clothing and keeping it organized (to make it especially easy if you're staying in a new hotel every night) is to use packing cubes. The packing cubes will help compress your clothing - which is key for making sure those bulky, fleecy, fluffy items will fit in your luggage. And, then you can separate each category of clothing into different cubes. It's the same concept as having a chest of drawers; one drawer holds tops, another holds bottoms, another has socks, and you open each one to grab what you need instead of digging around just one large compartment holding everything with zero organization.

However, because in this scenario, I assume your bag will be jam packed (I assume this because mine was) I recommend packing half with cubes and half loose. If you have packing cubes that happen to perfectly fit in your bag like jigsaw pieces, I'm jealous. But in general, packing cubes are probably a little awkward and there will likely be some valuable space being wasted in between them. So, put all of the smaller items, like socks, shirts, and tanks in packing cubes and then use fluffier, squishier items, like a sweater to fill in the remaining space.
Airport Outfit
To reduce the volume of stuff you're putting in your bag, wear some bulkier clothes and bulkiest pair of shoes to the airport. And plan on wearing a similar outfit on your way back.
Tote Bag
One final packing tip is to have an extra tote bag or two for convenience's sake. As I've mentioned again and again, unpacking and repacking luggage daily is annoying (especially if you've stuffed your bag to the brim) so make it a little easier with a tote. You can throw in your accessories and toiletries (stuff you want to be easily accessible) and keep your items separated since your rental car won't oppress you with luggage limitations like an airline will and this will free up room in your luggage, making it easier to rifle through and pack up daily. Plus, tote bags barely take up any room in your suitcase so you can pack a few without it being an inconvenience.

(By the way, I love the little reusable mesh bags that Urban Outfitters have been giving out as shopping bags. They're really light but durable and pack easily.)

Carry On
It's important to pick a decent sized carry on. If you can, force yourself to use a smaller bag so that you're not overpacking. I used my little under seat guy and I managed to fit everything in. It was a bit snug in the end, but I managed to get the 20+ pieces (organized in packing cubes) into the suitcase along with my toiletries bag.

Good luck and happy travels!