A Weekend Away

Chicago in November would not be my first choice but I would go wherever Alicia wanted to celebrate her thirtieth. It was a short trip - just over thirty six hours - just right.

How To: Pack for a Weekend Away (3).gif

Philosophy: You need less than you think.

Time: 15min


  1. Find your bag.

    This is my go-to travel bag. It’s done 50+ short trips in two years and still looks good. I like that it has two compartments (upper and lower), pockets for smaller items, and fits in an overhead bin. If you want other options, I’ve read good reviews of this Lo and Sons one and I’m about to test out this Beis one.

    Before anything else, get your bag out and have it nearby.

  2. Check the weather

    There’s no point bringing things you won’t need. And you’ll feel prepared.

  3. Get out the basics

    These are things that don’t need to go with anything else. PJs, underwear etc. I like to put underwear in its own pouch. Fold these and place them on a flat surface nearby (bed, floor, tabletop), don’t pack anything yet.

  4. Pick a color palette

    This is key. It ensures that you only have things that go with each other. Two primary colors and one accent color. For this trip, I went with black, brown and red.

  5. Think in outfits

    Especially effective for shorter trips. You’ll have exactly what you need. Lay out one outfit per day next to each other, in chronological order, tops on top and bottoms on the bottom (as you would wear them).

  6. Add in Accessories

    Place any extras (socks, shoes, bags etc) alongside each outfit. Now that you can see what you’re wearing, choose three items of jewelry that go with everything (I took gold hoops and two rings). You’ll wear these while traveling so no need to pack them.

  7. Lay out your travel outfit

    I wear the same all black travel uniform every time I travel.

  8. Find any weather/activity related gear

    A raincoat, your hiking boots, a swimsuit & towel. I needed a scarf & a hat. Place it next to everything else.

  9. Get your toiletry bag

    I keep a travel toiletry bag filled and ready to go. It’s carry-on compliant. So everything in smaller bottles and in a clear-ish container (I use the bags Glossier products come in). Place your toiletry bag alongside everything else.

  10. Give it a once over

    Everything you’re taking should be laid out in front of you at this point. Make sure that you’ve got everything that you need.

  11. Pack

    I roll most things. Heavier items like jeans on the bottom layers and lighter things up top. I tend to pack with the outfit order in mind, so things I’ll need last will be further in the bag. Shoes always go in my lower compartment. Place your travel outfit + jewelry on top of your bag and leave it at your bedroom door.