Packing light is never easy but it gets even more difficult during the winter. Actively fighting the desire to pack for any situation kills me, but paying $50+ for a checked bag kills me more. My recent trip to London would have resulted in an additional $76 per flight!

A lot of factors have to be considered when packing – location, expected weather, length of trip, etc. Depending on your answers will determine which of these hacks can apply to you. Hopefully, you’ll walk away with a few tips to take with you the next time you’re packing to board a plane!

What I'm Packing

The Basics – 

  • 1-2 thin long-sleeved shirts
  • 2 pairs of jeans
  • 4-5 shirts
  • 1 leather jacket
  • 1 cardigan/sweater
  • 2 pairs of leggings
  • 4-6 pairs of socks
  • 8 pieces of underwear (bras and panties)
  • 1 pair of water-resistant boots
  • 1-2 pairs of sneakers or walking shoes
  • 1 small purse for daily use

Weather Specific Items – 

  • 3-6 pairs of warm socks
  • 2-3 pairs of fleece-lined leggings
  • 1 wool coat
  • 3-4 sweaters
  • Winter warm accessories
    • Gloves
    • Beanies
    • Scarves

Toiletries –

  • Toothbrush (travel size)
  • Toothpaste (travel size)
  • Deodorant
  •  Shampoo (travel size)
  • Conditioner (travel size)
  • Hair cream (travel size)
  • Hair gel (travel size)
  • Face wash (travel size)
  • Face moisturizer (travel size)
  • Foundation
  • Mascara
  • Eyeliner
  • Bronzer
  • Blush
  • 2 makeup brushes

Technology – 

  • Unlocked smartphone
  • Laptop
  • Kindle Paperwhite
  • All necessary chargers
  • Travel power adapter
  • Airpods or noise-canceling headphones
  • Portable charger

Find a Solid Carry-On Bag

There are a lot of options when it comes to travel luggage. Some people swear by backpacks, others won’t leave home without a roller bag. Figure out which option works best for you and run with it! Helene Sula, over at HeleneInBetween swears by her Osprey backpack. Other bloggers, like Alyson Haley, love their roller bags.

Once you find what works best for you, make sure your bag is within the airline’s carry-on limits. The Carry-On Guy has a great break down of that here. The likelihood is you’re overpacking so make sure that whatever bag you choose gives you ways to maximize the space you have.

Personally I have my roller bag (I found it at Ross years ago but here is something similar) and a backpack. I put all my clothes, shoes, and purse in the roller bag, while I put my toiletries bag and technology in my backpack. That way they’re easily accessible should I need to take them out for TSA but also, I like to refresh my face a bit before I land to keep it from getting dry from the circulating air on the plane. Depending on how cold I’m expecting it to be when I land, I may also take to packing my winter accessories (gloves, beanies, scarves) in my backpack as well. I always keep a pair of warm fuzzy socks on me because I know I get cold when flying.

Swap / Add Weather Specific Items

If you look at my list above, you’ll see I have a section for ‘Weather Specific Items’. These are things that I’ll swap out with items from the ‘The Basics’ list in the hopes of maximizing space while making sure I stay warm. I’ll swap out my regular leggings for fleece-lined ones that are thin enough to wear under jeans if necessary. The same thing goes for the socks, which get stuffed inside my shoes to consolidate space. Instead of 4-5 shirts, I’ll bring 2-3 shirts and 2-3 sweaters. My leather jacket gets swapped out for a wool coat or if you’re going someplace rainy/wet, look into a down puffer jacket like this. Those are great because they can usually be rolled and stuffed in a bag pretty easily.

Lay Out Your Packed Items

To keep yourself from overpacking, sometimes it can be helpful to visualize your outfit options ahead of time. I like to put everything out on my bed before I pack it in order to mentally build my outfits, mixing and matching pieces to maximize the use of them. Primarily, I wear mainly neutral colors with small pops of color so the options are endless! I also do this with any tech or toiletries so I can just think about what might be in excess or unnecessary.

Roll Up Your Clothes

A few years ago I embraced the use of packing cubes. These babies are revolutionary; they keep things separate but organize, they are shaped by whatever bag you put them in, and they expand the items you pack. When I want to maximize the space in any bag, even if I’m not using packing cubes, I roll all my items. It’s a great way to open up extra space you didn’t know you had, filling every nook and corner of your bag.

Wear Bulky Items On Flight

It obviously won’t be the most comfortable experience wearing your thick coat or heavy cardigan for the entire flight. However, taking the bulkier items out of your bag will save on initial space. Once you’re in your seat you can use these items like a blanket or pillow, or if they aren’t needed put them in the overhead bin. I wear my boots on the plane which isn’t ideal but worth it for space. One pair of boots can easily give that space back to several clothing items.

It can seem like a daunting task, trying to fit your life into a tiny bag. Just remember, baggage can be cumbersome. You’re traveling to experience the world beyond your front door. Try to focus more on enjoying your trip instead of being frustrated that you overpacked again.

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