Reader Question: What to pack?

Gap green stripe dress // Splendid nautical stripe dress

Here’s an email I got from Beth, a longtime reader and friend:

Hi Rachel!  I’m writing with a post request/suggestion!  I would love to see your take on vacation fashion. Specifically, vacations with a lot of walking. I know you went to Disney recently, as are we!  I always find it is such a challenge to find something comfortable for extended walking, while at the same time feeling good about what you have on.  Bulky tennies and fanny packs need not apply 🙂  Long ago you posted about the Cole Haan Gladiators, and you were so right – they were so comfortable without being frumpy at all!  Thanks!

Great question! And this is always my dilemma too – how to look stylish when you’re on the move. Vacations like San Francisco or Disney are tough because you have to dress for outdoor weather with lots of walking. You’re probably going to be out and about all day long, but you want to feel stylish and fabulous. Not like you just fell off the turnip truck.  Big cities are easy; in cooler weather, a stylish trenchcoat w/ comfy ballet flats, a drapey tee and leggings gets you through the day when you’re not sure what the weather will do.

But let’s address Disney because frankly, that’s a whole mess of crazy happening there. When we went in February, I really struggled with what to wear because I was way freaked out by all the online talk of fanny packs and frumpy tennis shoes. But now, on the other side, the bottom line is this: dress for comfort and style – but comfort first. You’re going to be walking your buns off, so build your outfits around your comfiest shoes.  Plus you’re waiting in lots of long lines, often outdoors, and baking in the sun.  You will see people in all types of clothes; what you won’t see much of is dressy stuff.

Splendid dress (also in plus!) // Gap dress

So my main advice to you for Disney if you don’t want to be the typical tourist? Dresses will be your friend. Especially tee-shirt dresses. Maxis, minis, midis – anything will be perfect. You’ll be stylish, comfortable, and if need be, it’s easy enough to layer on a jacket or a cardigan if you need to.  When we went, I lived in my J.Crew striped maritime dress (see this year’s version below on the right). It was heavy enough to keep me happy in the cooler morning hours and evening, but comfy enough that I still felt pulled together and casual enough for the occasion.  I belted mine and kept it simple.  Also? These will work perfectly for Beth’s San Francisco trip, too. Again, layering will be the key since SF tends to be so chilly in the summer.

JCrew garment dyed twill dress // JCrew Maritime dress

Let’s talk shoes. Beth mentioned the Cole Haan gladiators I bought a few years ago that are insanely – INSANELY! – comfortable. This year’s version are these – and while I haven’t tried them personally, I have zero doubt they’d be fantastic.  The Toms ballet flats would also be perfect – but buyer beware. Size down significantly if you order them online. They run extremely large.  Another great option for casual comfort when you want to indulge your inner prep is the Sperry Top-Sider.  These shoes can take a beating; pair them with not-socks to keep your feet happy while walking through the day. Finally, the one thing I specifically purchased for our Disney trip was a pair of retro-styled sneakers. I wanted something with the comfort of a sneaker but without the look of your typical running shoe. Running shoes are ONLY to be worn for RUNNING!  Other great options are vintage-style Adidas or Pumas.  Be careful how you style these with the rest of your outfit, though; try them with cute shorts or shorter skirts. Anything else heads to frumpland.  And you don’t want to go there; you are going to Adventureland, my friend!

Cole Haan Kimry // Sperry Top Siders in gold // New Balance U420 // Toms Ballet

So tell me — what is it that you like to wear when you go on family vacation?

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  • laura @ hollywood housewife

    Great tips!  I love the look of the Toms ballet flats, but when I tried them on in the store, they were wildly uncomfortable.  I was confused.  Maybe it’s just my foot?  Can anyone testify to their wearability?

    • RachelShingleton

      My only experience was that they were too big – I had ordered them online and my size 8 foot was swimming in their size 8.

  • Michelle Otahal

    In March we went to San Diego, I packed dresses/cardigans and probably the best investments- Sperry Top- Siders in pewter. We walked legoland, the zoo, sea world, etc. and I never got a blister and the shoes did not hurt my feet – major plus!

    • RachelShingleton

      Ooh, good to know! I’m glad I’m not the only one who’s in love w/ those comfy shoes!

  • i LOVE wearing shorts and sandals with a pretty light blouse for summer theme park vacations! LOVE all your dress choices! 

    • RachelShingleton

      Thanks, friend! Ok, from all your instagramming, you need to do a style blog! You always look amazing!

  • MiaOKC

    Perfect, timing, Rachel! Am packing tonight for the beach. I will be planning all my outfits around swimsuits and flip flops, though. 🙂 I do love those Toms flats you show. I feel too un-hip to wear the traditional Toms. Not cool enough for elvish burlap, I guess.

    PS – I missed your blog! My google RSS didn’t update to your new feed and I thought you were on some kind of extended vacation. When I went back to wistfully read your last missive to the world, I started clicking around and POOF! There you were! I will have to catch up on all I’ve missed.

  • I must reiterate to have a cardigan on you at Disney! It can be warm outside and then really cool inside. 

    Jeremy and I are about to head off to Europe for 2 weeks of going wherever the wind takes us and 1 week of serious trekking. So packing for the two (chill & chic + adventure) is a little complicated because I only have so much room in my backpack.  So basically I’m taking some lululemon gear that can double as chic leggings or a simple cami + ballet flats (Ballasox) + a thin BCBG black top + black skinny jeans + black tailored shorts. DONE. 

    • RachelShingleton

      You’ll be perfect for Europe. I LOVE Lululemon. I could go nuts in there.

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