How to Pack for Travel

On Saturday I booked a trip to leave on Monday for 5 days in Puerto Rico. One of my goals when I started Dean Street Society was to take my very first grown-up Caribbean vacation within the year to celebrate this new chapter. Mission accomplished.

It was a gloriously spontaneous Dean St Retreat & marvelous to have the head space to read books on style & life style, & dream both big & small about what I want for Dean Street Society & for you in the coming months. And because I never do anything these days without thinking of you bettys, I've got lots of on-the-road style posts in the weeks to come. Starting with how to pack in a carry on for a trip abroad! Here's my tips on how I conserve space without sacrificing style.


1.What's the #1 thing you want to take with you? To London this summer it was my new marigold skirt. To Puerto Rico it was my black bikini. This means every thing now revolves around that one piece & if it doesn't go with it, it doesn't go on this trip. What goes with a black bikini? Black flip flops & black ballet flats. So any cute sundress that went with navy boat shoes or bronze ballet flats, stayed home.

2.What's your color palette? Once I had my two pairs of black shoes & some of my favorite cover-ups, a color palette started to emerge of mostly black with strong pops of color. A last minute trip to Target confirmed this when I picked up two sun hats with brightly colored rims. The point is that everything should be able to easily remix with each other so you don't have to go day by day planning out necklaces & cardigans before you arrive. You can go with the flow, adapt for weather & changed plans, & know that you won't get down to your last two days & have clashing ensembles or pieces that go with nothing.


3. Pack for each day, plus one. You do not need endless options. But having one extra gives you some breathing room to still have options on your last day. And if you wear something for 3 hours to dinner, you can re-wear it. For 5 days I had 6 outfits:


3 shirts/2 pants (1 shorts, 1 skinnies for travel; both black) + 3 dresses

3 pairs of shoes (flip flops, ballet flats, hiking)

1 nightgown + 1 hiking outfit

1 cardigan that went with everything

1 bathing suit

17 accessories (4 head scarves, 4 necklaces, 2 headbands, 2 sunglasses, 2 hats, 1 neck scarf, 1 watch, 1 belt)

Style Tip: 17 accessories?! Yup. Accessories are a great way to leave yourself room to play & make outfits remarkable in pictures, but take up little space. Rather than shoving two more dresses in your carry-on, bring another necklace & scarf. If you end up not wearing a few in the end, you don't feel annoyed you schlepped the weight of that additional pants/shirt/sweater combo. I had 4 pieces I never wore, but the options allowed me to pack in under an hour & never feel sartorially stressed while there.

Now it's your turn to spill. What are your secrets to packing light? Or do you have any questions I didn't cover? Would love to hear! 

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P.S. Part of the impetus for this spontaneous trip was a pretty major annoucement coming around the corner. Are you on a part of Honor Society? Join with your name & email on the sidebar as I would love to share my joy with y'all first! 

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