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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