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Summer Travel Outfit

Retro travel clothes

Retro Travel Outfit

Retro travel outfit

Retro Travel Outfit

Retro Travel Outfit

There are several things I like to keep in mind when dressing for summer travel:

1.) Comfortable shoes – I’m going to be walking all day!
2.) Make sure my armpits are exposed – nothing is worse than having a clingy shirt around my sweaty pits!
3.) Use a cross-body purse – harder for someone to steal and it’s much more comfortable to be hands-free.
4.) Pants or shorts that keep their shape and don’t get stretched out and saggy after a day of traveling. (Summer dresses are great – but they have to be long enough to not have a Marilyn Monroe moment every time there’s a breeze.)
5.) Keep my hair out of my face – a headband is usually a cute, comfy way to do so.

This is a summer travel outfit that embodies all of these things. I wore it over the weekend, while I was in Philly for the 4th of July celebrations. It was an absolute blast! (I’ll be putting together a separate travel post on Philly very shortly.) The day I wore this outfit was quite muggy and required a ton of walking and standing – however, I was comfortable almost the entire day.

The only time I started to feel a bit uncomfortable was by the end of the day (10-11 at night), because my feet were swollen. My Salt Water sandals are really comfortable, but even they can’t keep up with a full day of walking without properly hydrating (rookie mistake!). I was quite impressed with how long these sandals were comfortable for, though. I was constantly on my feet, and feel the only way I would have been more comfortable would have been to wear my running shoes.

Retro Travel Outfit

My shorts are my absolute favorite part of this whole outfit – and I hate wearing shorts. Generally, I feel like my shorts are constantly riding up in places they shouldn’t be, or they are too big in the waist or cutting off circulation to my thighs if they do fit my waist, or they’re way too short or awkwardly long, etc. These shorts fit me perfectly, though! They are so comfy and stretchy and breathe well. I don’t have a single negative thing to say about them.

Sorry for constantly using this ladybug purse, but it just goes with so much of my clothing! And I love that’s it’s a crossbody – perfect for traveling and walking all day.

Personal Styling by Lindsey

On a side note, this was also the day I officially became a personal stylist with SIDE by STYLE! I am super excited about this new style venture!

Kathy of Lace & Whimsy had designed my “Hire Me” button. She is also able to create very detailed blog buttons and headers. The button above is one she created for her own site. How cool is that? Be sure to check out her Etsy store by clicking here.

Needless to say, this was an all-around exciting 4th of July weekend – from starting a new career venture to exploring Philly! How was your 4th of July? And what do you do to stay comfortable during a full day of traveling? Let me know in the comments!

Where to find it:

Sandals: ModCloth
Shorts: ModCloth
Top: ModCloth
Cami: Maurices
Purse: Amazon
Headband: ModCloth
Flag Pin: Etsy
Watch: Walmart (similar)
Sunglasses: Burlington Coat Factory (old)
Earrings: Claire’s (old)


  1. Liana of Finding Femme says:

    I have these exact sandals too and they look so classic with high waisted shorts. You’re so good at travel clothes !!!


    1. haveclotheswilltravel says:

      Thank you so much, Liana! I seriously want a pair in every color. 🙂

  2. I love how well you marry comfort and style. I struggle with that when traveling in summer weather.

    1. haveclotheswilltravel says:

      Thank you so much, Kristian! However, I would say your travel outfit for the Met was perfection. 🙂

  3. I love the ladybug bag.

    1. haveclotheswilltravel says:

      Thanks, Jessica! I use it way too much – but it’s just so much fun. 🙂

  4. Lauren Blair says:

    Sooooooooooooo cute! Those shorts are awesome; I see why you love them! We seem to think alike with sandals with ankle support for ::sigh:: practical:: shoes and I do cross body purses when traveling too for the exact same reason. Great minds? 😉 Great post, lady! XO
    -Lauren Blair

    1. haveclotheswilltravel says:

      Thank you, Lauren! Haha practical shoes are an evil necessity some days. 😉 Great minds think alike! 🙂

  5. Adela Acanski says:

    Nice look! <3


    1. haveclotheswilltravel says:

      Thank you, Adela! 🙂

  6. Such a cute outfit, girly! I love the headband so much. I totally agree with you about all of these tips! Comfortable sandals are my go-to and nice denim shorts! A cross-body bag is a must too or I like to use mini backpacks! 🙂
    Olivia | Her Name Was Celebration

    1. haveclotheswilltravel says:

      Thank you so much, Olivia! And I have been meaning to get my hands on a mini backpack! They seem like they would be such a comfortable and cute alternative to a purse. 🙂

    1. haveclotheswilltravel says:

      Thank you, Sabina! 🙂

  7. Amanda Brezovsky says:

    These sandals are so cute and definitely look comfy. Girl, wear that lady bug purse alllll the time! Glad you had a nice time in Philly!


    1. haveclotheswilltravel says:

      Thank you so much, Amanda! I hope you had a lovely weekend, too! 🙂

  8. Ela (@WunderBliss) says:

    Totally need a pair of red sandals like the ones in this post! I love them and they are the perfect summer staple. Make as much use of that lady bug purse as you can because it’s gorgeous and then you can definitely get ur money’s worth;) Hope you had an awesome 4th of July weekend.


    1. haveclotheswilltravel says:

      Thank you, Ela! And definitely get yourself a pair of Salt Water’s – you won’t regret it. 🙂 The lady bug purse will more than likely be used to death, haha. Hope you had a wonderful Canada Day!

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