How to Pack for Holiday Travel: Christmas, New Year’s, and More

Megan Lee
Look your best at your 1st (and 11th) family holiday gathering this season. From play dates with nieces and nephews, to religious observances with your grammy, its possible to pack carry on only and still look your best this holiday season. Here’s how to pack for holiday travel like the shiny, bright holiday star you are.

Holiday Carry On 101

Come sit on Santa’s lap for some real talk. The best way to avoid the pending headache of busy holiday travel is to travel carry on only. “One time when I went to a relative’s house, I brought one suitcase and came back with two suitcases. I had to tube home and ended up having a stranger carry my bags because I was too slow. Don’t do what I did,” warns Abi Davis. We all know that holiday travel is synonymous with crazy, crowded travel with weather delays that are constantly looming. So, how should this impact your packing plan? “Always avoid having connecting flights near Christmas in Chicago or the east coast of the USA! Either pay extra for a direct flight or connect somewhere with low risk for bad weather,” shares Rachael Howell, an American expat in Rotterdam. International adventurer Alisa Tank echoes her sentiments: “But if you have to connect, try to only bring a carry on so you can be nimble if there are delays!”  With delays and cancelations often come lost luggage. Here’s what to do if that happens, and how to avoid lost bags. Keep it simple and light by packing carry on only—it might sound crazy at first, but it’s easier to do when you maximize liter allowance by two-bagging your holiday travels with the Laptop Backpack and Setout Duffle Bag. If you really need to carry as much as possible, a full sized travel backpack, like the Setout Backpack, paired with a personal item sized duffle bag can be the perfect combo for squeezing every inch out of those airline carry on allowances. Also, plan to deal with longer security lines loaded with the folks who only travel 1-2 times per year. And, let’s face it, they just don’t have our efficient TSA systems down pat yet!

Oh the Weather Outside is Frightful…

Packing for holiday travel can feel daunting, between winter weather and holiday parties, there are a lot of bases to cover. Less is more. Start with this sound advice from adventurer Kerissa Snyder: “DON’T pack ANYTHING that can only be worn once, or only one way (a shirt that only works with one pant, the formal dress that can’t be casual, the casual dress that can’t be dressed up, high heels, etc).”  Pack with layering and flexibility in mind.

How to Pack Cold Weather Clothes

Packing your bulkiest items is no easy feat. Stuff your heavier items, rolled up, in the bottom of your bag. Fill the remaining empty space with lighter items, your wool socks and underwear (you don’t need more than 2-3 pairs of each). Other compact cold weather accessories, like hats and gloves, can also be shoved in remaining spaces or stuck into your coat pockets if need be. Wear your bulkiest items on the plane—like your sweater, jacket, boots and a scarf. You can sacrifice a little comfort for a few hours in anticipation of the cold ahead. Keep reading for more tips on packing for a cold weather trip.

Going Somewhere Tropical? Pack for Warm Weather 

If you’re one of the lucky few heading somewhere warm for the holiday season, you won’t have to worry about boots and a winter coat. You’ll have a much easier time packing larger quantities of items (swimsuits are miniscule compared to parkas), but resist the urge to overpack. Less is still more, and you definitely want to avoid checking a bag, lest it get lost in that weather delay in Chicago coming home. Leave the boots and tights and scarves behind in lieu of sun hats and sun block.

How Pack Carry On for the Holidays

Packing carry on only is possible, even during the holidays. Here are the best tips for how to get it all in:

Roll and Fold

We tested the theory and it turns out—rolling is better at keeping things organized, but folding is better in some circumstances.  Smart packers use a blend of both rolling and folding.

Wear Heavier Clothes

Wear your heavier clothes on the plane, think jeans, boots, sweaters—even if it’s 80+ degrees out when you leave your current location. Save space and weight in your bag by wearing, instead of packing, your heaviest clothing items. Stuff that winter jacket in the overhead bin once you find your seat, or roll it and use it as a pillow to get some sleep on the plane.

Pack Layers

“If you’re at home, you’ll likely have access to laundry facilities,” Kelsey reminds us. Who cares if you wear the same jeans all week! Reduce the number of layers by choosing items that do double duty. Fellow traveler Kerissa Snyder swears by bras with convertible straps. Go from t-shirts to that New Year’s Eve dress without changing your base layer.

Try the Two-Bag System

The combo of a Laptop Backpack and Setout Duffle Bag will have you smooth sailing at the airport—even with connections. Pack your laptop to get a little work in around the margins of your holiday, or escape with a mindless movie. And there’s room for that extra pair of holiday shoes built into the duffle. Sweet.

Bring Items for “Me Time”

Extended time with extended family can be Stressful with a capital S. Caroline Odell recommends, “Do something—and pack something—to get some space. Go to a coffee shop with a book, work out at a gym nearby…” Alex reaffirms: “Prioritize running shoes so you’re able to escape family drama!”

Pro tip: Leave a Winter Coat With Family

As Jacqueline advises: “Just have them bring it to the airport when they pick you up.” Genius.

Packing for Holiday Parties & Fun

The holidays come with parties and special traditions. Plan ahead and pack what you need for your holiday adventures

Classy Parties—NYE Bash, Christmas Eve Service, Hannukah Parties

You want to look your best as you wrap up this year and look ahead to the next, not to mention Grandma always has opinions. Make sure that you pack at least one nice, dressy outfit to knock their winter boots off. For men, this means a dressier shirt with nice slacks, a travel blazer, and  hip shoes—maybe even a fun and festive pair of socks. Ladies, the sparklier the dress, the better. Paired with opaque tights, your go-to boots, and your favorite dangly earrings, your look will be as classic as It’s a Wonderful Life.  Or, pack a more functional dress and glam it up with accessories.

Ugly Sweater Parties

Nothing says Christmas quite like a tacky sweater. Roll and pack your brilliant thrift store find, or purchase one last minute on Amazon (direct shipping to your destination can be a space—and life—saver). Alternately, hit a thrift shop when you land and roll the dice on what you’ll find. Guaranteed to be ugly. Don’t forget comfy bottoms for this shindig because you’re definitely going to overeat at the snack table (You in the future: “Sorry for eating the whole gingerbread house”).

Cozy Mornings

Enjoy cold winter mornings with thick cozy socks (leave the bulky slippers behind and try to borrow dad’s extras instead), a warm fleece, and soft sweatpants or leggings. Just add a mug of hot coffee and a candle and you’ll be in peak hygge.

Functional Footwear

No need to treat your local mall like a runway with your seasonal selection of boots. Take the practical road and simply pack a pair of winter-friendly shoes (appropriate for wherever you’re headed) in addition to a second pair of your choice for when you’re ready to glam it up and party. And no, you don’t need that third pair. You really don’t.

Family Gatherings

Convince your family that you have your life together (you do!) by packing an outfit that doesn’t come across as haphazard. Start with a basic travel wardrobe and then add a sweater, or a blazer, depending on whether you’re headed to playdates with nieces and nephews, coffee with that old friend you lost touch with, dinner with your old crew, or an early morning breakfast date with dad. Aim to pack outfits that evolve.

Packing Presents

How to Pack Gifts

For gifts you’re gifting: Just ship direct! Especially for those traveling carry on only this holiday season, making room for gifts can be a bit of a chore. Our best advice? Ship gifts to your destination instead of packing them in your luggage. Holiday packing expert Kelsey Howard shares: “Send gifts directly to your destination with Amazon or other online shopping vendors if possible. Wrap them when you get there!” For gifts you’re receiving: Request portable gifts in advance. Jacqueline Lunsford expands: “I always reserve some extra space in my suitcase because I know I’m bringing stuff back with me gift-wise, whether I like it or not.” Another option is to let loved ones know ahead of time that you prefer gift cards, or shipped items. “If it’s something my mom knows I’ll like a lot and is bulky, she’ll buy it online and have it shipped to me at my home address,” Jacqueline continues. If you know that your family would rather watch another rerun of A Christmas Story before gifting you something as generic as a gift card, follow Alex Prigge’s tip: “Sometimes I will pack a small bag inside another on the way there to bring gifts back with me.” Or, you could head to the post office and ship your packages back home, rather than carry them on the plane. It’s probably less expensive (and risky) than checking a piece of luggage n your flight back!


Erika Pfaab sums it up best: “Don’t go overboard thinking of ‘what if’ scenarios.” Less. Less. Less. Be Scrooge-like in your analysis of what to leave out. Learning how—and what—to pack for holiday travel doesn’t have to be a Christmas miracle.
  • Stick to carry on only and expand just a bit to two-bag travel
  • Pack smart, in layers and multi-functional pieces
  • Buy the ugly sweater when you get there
  • Take just one extra pair of shoes 
  • Ship gifts (going and coming!)

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