I used to be the kind of person who carefully plans her vacation outfits; after all, I am the kind of person who carefully plans her outfits all the time, and a vacation offers a whole new scope for expression. But after having kids, and travelling with them over the years, I’ve mostly given up on it … when it comes to family vacations at least. I pack for comfort, durability, and accidents. If something were to happen to my luggage or my clothes, I don’t want to stress out about it.

Buuuuut … I also want to look cute.

By now, I have a fair bit of experience with resort vacations, so I know what to pack (lots of dresses) and what not to pack (jackets, jeans). I try to pack as light as I can, if only because I don’t want to lug around a bunch of extra weight; the kids’ “necessaries of life” are sufficient — not to mention my books! On this trip, I packed 5 dresses, 2 tops, a pair of shorts, a pair of lightweight pants, and 4 pairs of sandals (all of which are shown below) in addition to my swimwear and beach cover-up. [I’m not counting my plane clothes which consisted of a t-shirt, hoodie, leggings and tennis shoes.] The only other things I packed and did not end up wearing were a cardigan (it never got cold enough in the evenings) and a 3rd top.

The stuff I took with me took up hardly any room – everything could be rolled up — and was more than enough for the 7 days we spent at the resort, even with several daily changes. To give you a sense of what I mean, here is what I would typically wear:

  • AM: swimsuit plus cover-up and sandals for breakfast and morning activities (usually beach and pool);
  • lunch: ditch the wet swimsuit and change into dry cleans (shorts, my linen tunic, or pants)
  • afternoon: (fresh) swimsuit and cover-up for more beach time
  • PM: dress (or pants) for dinner

I don’t like being wet at meals, hence all the changing. The resort “dress code” is about as lax as they come, so there is no requirement to “dress up” (i.e. wear something other than a swimsuit) except for certain restaurants and dinner time.

Here are some of my mid-day outfits:

As you can see, I kept things pretty simple. The two tops worked well with both my shorts and my pants, and were nice “beachy” colours. The white, windowpane print linen tunic also doubled up as cover-up, sans belt.

For dinner, I made a little bit more effort, but only barely – usually by adding a necklace, and occasionally some higher heels.

6 Comments on What I Wore: Vacation Edition

  1. You look great in all of these but my favorites are the outfits featuring the printed dresses. They feel perfectly beachy-dressy and I like that the heeled sandals are colorblocked and give more fun/vaction vibes than if they were solid black or white.

    Also love how you styled the white checked dress with the bow. I feel like I always see that type of dress styled the same way (loose, with clogs or those asymmetrical pointed-toe leather shoes that have been popular) so this was refreshing.

    I also prefer dresses for warm-weather vacations even if there is not much swimming involved. Much breezier and I enjoy the opportunity to use my purses.

  3. Your vacation wardrobe is on point. Loving all your dresses! And this post reminded me that I have those same shorts…I need to pull them out and see if they still fit!