Dressed Down / Styling

How to Pack for an Adventurous Vacation

Some of you beautiful people followed along with my Alaska trip via Instagram. (Thank you for all the lovely comments!) For those who didn’t, I just got back from 10 days in Southeast Alaska on The Alaskan Dream, a 40-person catamaran cruise ship. It was a once-in-a-lifetime experience, and I highly recommend visiting Southwest AK if you get the opportunity.

Many of you asked me how I packed for this trip, since it wasn’t a typical vacation. Because we’d be living on a boat and doing more outdoorsy stuff than usual (hiking, kayaking, and other water-related activities), I couldn’t pack my “normal clothes.” So my usual fashion-centric ensembles would have to be rethought. I also wanted to fit everything into one mid-sized duffel bag (I’m practicing light packing for another big trip we’re taking next year).

Because weather in Alaska during the summer season can range from 50-90 degrees, I had to think about layering, flexibility, and complimentary pieces. Besides the wide range of temperature fluctuation, it rains almost every day in Southeast AK (it’s technically a rainforest!), so I had to consider waterproof/weatherproof gear. I focused on packing neutrals with the occasional statement piece that could easily be layered over other pieces. I also needed everything to be flexible—pants had to work with multiple tops, jackets, and accessories, and vice versa. In the end, I won the unofficial award for lightest luggage, which is a major feat for this notorious over-packer.

The following is everything that I packed (excluding undies/socks/toiletries):


Every pair of pants I packed were roomy enough to be layered over my thermals if the temperature dropped. They’re also mostly neutrals and would work with every top I packed.

  1. thrifted camo pants (last seen here)
  2. REI waterproof hiking pants
  3. Trouve windowpane slacks
  4. vintage Liberty overalls


Save for the graphic button down, each top I packed was a neutral and could layer seamlessly with one another. The top three worked as base layers, while the last four could be layered over if I needed more warmth.

  1. long sleeve mini-stripe base layer
  2. Uniqlo heat tech
  3. thrifted baseball tee
  4. vintage graphic tee
  5. plaid button down
  6. mid-weight striped long sleeve
  7. statement graphic button down



I packed outerwear in the same red shade (and chose a patterned sweater that also included red) so I could layer them easily without worrying about inharmonious clashing colors.

  1. REI waterproof/windproof shell
  2. graphic sweater coat (not the same as mine, but close)
  3. Patagonia insulated down jacket



I streamlined the accessories I brought because I knew we’d be fairly active the entire trip. Jewelry and purses wouldn’t be necessary. Instead of necklaces, I packed two bandanas whose colors worked with the top/pant combos. Hats and bandanas are an easy way to add color and pattern to an otherwise neutral outfit. I had to be pretty practical when it came to shoes. I bought these Teva hiking shoes specifically for this trip and they did not disappoint. IF I could do it again, I would not pack the stacked heel boots. I only ended up wearing them once, and probably didn’t need to bring them.

  1. Topo baseball cap
  2. Carhartt knit hat
  3. New York Hat Co. printed baseball cap
  4. RayBan Gatsby
  5. red bandana
  6. shibori bandana
  7. Teva waterproof hiking shoes
  8. stacked heel lace-up boots
  9. Converse high tops


I didn’t take photos of every outfit (Sorry! I was busy watching whales and eating freshly caught salmon🤷‍♀️), but here are a few of the outfits I was able to put together over the 10 days we were gone.

What are YOUR packing secrets? Please share them with me in the comments!

How to pack for an adventurous vacation in one suitcase. How to pack for Alaska.

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