Style Translator: A Casual Cool Outfit for Traveling

Jul 23, 2015

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Converse Chuck Taylor All-Stars ($55) // Colored Navy Stripes Dress ($20) // Ron Herman Panama Hat ($146)

Looking good while traveling isn’t easy.  If you plan to walk, you need comfortable shoes.  You need to pack well without taking up much space.  And you need to choose accessories that can work with multiple outfits.  But this Pinterest photo nails the perfectly casual, undeniably chic tourist look to which we aspire.

Cool Comfy Shoes. $4 flip-flops are for the pool deck and nowhere else.  Birkenstocks are anything but chic.  But a pair of low-profile, understated sneakers are both comfortable and stylish.

These Chuck Taylors have a slick, vintage vibe to them.  I prefer a pair of easy Keds.  I also like these chic New Balance sneakers with metallic accents.  Either way, you can baby your feet a bit and look stylish.

Relaxed Dresses. I adore casual shift and sheath dresses.  They can easily be packed in a suitcase or weekender.  They’re also versatile and comfortable.

I’ve never purchased anything from the retailer that makes this striped dress, so I can’t vouch for quality, but I thought it was pretty cute.  For a more traditional striped dress, this dress from Gap and this Tim Tim Stripe Dress from French Connection are good choices.  Plus-size readers should try this ASOS Curve dress.

Chic Accessories. I love the way this outfit is styled.  The Panama Hat is a lovely option for protecting your skin while you walk around town.  For something cheaper, try this hat from American Eagle.  I also like this fedora from San Diego Hat Co..

The blush crossbody bag is another great pick.  It’s pale enough that it works as a neutral, but it has just enough color to give a bit of pop. This Kate Spade flap bag is a gorgeous option.  For something inexpensive, Forever21 has this simple bag.

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  1. Sara says:

    Glad I’m not the only one who travels in dresses. I always get weird looks when I show up at the airport in a casual dress. They’re so easy to layer up or down if the airport/airplane are too cold/hot, easy to move in if you struggle with your luggage, they don’t get twisted around you like jeans do when you try to squeeze into a window seat. If you wear one with tights in the winter, you don’t have to worry about packing boots (security checkpoint may be an issue, but beats the heck out of sitting on a stuffed suitcase and your boot heel is sticking out). Dresses are such a blessing.

    • Kate says:

      Until you get selected for the full pat down . . .

    • D says:

      I prefer pockets when I travel. Sure I have to empty them out for TSA, but I always have my chapstick and earplugs on hand without rooting through my purse. I’m not trying to sell you, though, you do you.

  2. B says:

    Not to be a contrarian, but I’ve seen some cute Birkenstocks out there now – they’re not just the brown sandals anymore!

    • Monica says:

      Ditto, I just got a cute pair for summer and wear them every day! I’m sure they’re not for everyone, but they have a ton of varieties now!

    • Rebecca says:

      I agree – I have some light blue leather ones that I think are pretty feminine, and comfortable. They’d go nicely with the dress in the post!

    • xxx says:

      I have some red patent leather birks that would be amazing with this dress.

    • H. says:

      I love my Gizeh sandals (which I’ve had for years in a sort of shiny slate blue); they are SO comfortable. (And honestly, I find their simple style more attractive than many “fashionable” gladiator sandals that strike me as hideous.) And tons of celebrities seem to agree — if you Google for “celebrity Gizeh” images you’ll get everyone from Heidi Klum to Anne Hathaway to Julianne Moore wearing them while casually walking around town.

  3. Jenn S. says:

    This was a great post – I haven’t flown in a while and thankfully my job does not require that I do, but I’d probably wear an easy dress like mentioned or leggings with a tunic.

    A follow-up question to this – it isn’t a scenario I have faced, but I’m sure people who read do face it. Sometimes you might be traveling for business with your team. Do you have different suggestions for dressing for those situations, or would you approach it the same way under the (assumed) understanding, “We all know flights are uncomfortable, so I’m being both put-together AND comfortable,” even if it means appearing a bit less professional than you usually prefer in that the company of your colleagues?

  4. E says:

    Love this. Thanks, Belle!

  5. S says:

    I wish I could wear a dress while sightseeing but I find that I get inner thigh chaffing which traveling during summer months. Any tips for appropriate shorts to wear under these dresses that aren’t constricting but still keep the friction at bay?

  6. Diane says:

    What if you’re short? I feel like when I wear converse with a dress my legs look stubby.

  7. Gabby says:

    Maxi dresses (with a cardigan) are my travel hero. Get one in a soft jersey, and you’re always the right temperature on a hot OR cold plane and you look like an adult but feel like you’re wearing jammies.

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