What to Wear: Road Trippin’!


what to wear

For this edition of What to Wear, we are going on a road trip!

what to wear on a road trip

I love a good road trip and I’ve driven across the country a few times as well as lots of small, one-day-across-state-lines trips. That being said- I am one of the worst road trip partners because moving vehicles put me to sleep. The harder I try to stay awake, the more incessant the need for Z’s is.

what to wear on a road trip

sweatshirt: Etsy shop Kin Ship
head scarf: vintage, thrifted
infinity scarf: Free People via Last Chance
shorts & tights: F21 (last year)
boots: vintage, ebay
vintage bags: thrifted
headphones: Urbanears, xmas gift from my mother-in-law

vintage luggage

I like to be comfortable in the car but I don’t like to show up at the destination, or stop to eat wearing pj’s. I usually wear a comfy dress or shorts with some tights or leggings and easy-on/off shoes.

what to wear to fly

Would I really bring headphones on a road trip? No. I’m not that awful of a travel buddy. I was thinking of our flight to Missouri next week and this is pretty much my outfit recipe for flying too. See how I multi-tasked that? ;)

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18 Responses to What to Wear: Road Trippin’!

  1. You are so bloody cute. I love the colours of your vintage bags with your outfit. And, that sweater is so adorable.

    Great outfit, Lisa!

  2. Amanda A says:

    Ahh! You look so damn cute! And I LOVE those two travel bags. I never see mustard or red. I always put them in my shop; why don’t I keep one for myself?! If you put on a coat (and mittens and snow goggles, hah!) this would be the perfect outfit to roadtrip to the Minne!

  3. That is totally an outfit I would wear for a road trip! Super cute!

    I also ALWAYS fall asleep on road trips! I feel bad for my husband, but on the other hand he can’t fall asleep in the car and really enjoys driving! So maybe we’re the perfect road trip pair!

  4. Linn says:

    The sweater is so cute and I love the way you wear the head scarf. Relaxed, yet chic!

  5. Dus says:

    Haha I hadn’t even thought of that but ya that’d be pretty bad if you just put on your headphones and ignored your fellow road-trippers haha. Is that your van? That thing looks so old and cool and like you could even live in. Absolutely love your road trip outfit- such a great idea to go w/ comfy shorts + tights & I absolutely love that sweater! You’re just the cutest not forgetting a scarf & cute headscarf too, great ideas for my own travel outfits, which i tend to overlook.

  6. Sarah says:

    That truck is awesome, and I love these photos; everything about them. You’re super adorable. That sweatshirt; gah! Your whole outfit, and that luggage are amazing.

  7. Marlyn Pena says:

    Such a cute and comfy outfit! I am the opposite of you on road trips. I’m always paranoid that my hubby is gonna fall asleep on the wheel so my eyes are pretty much glued open! Moving vehicles put him to sleep too. Haha!

  8. I have that same red bag (only mine is more *worn in*) I got it for $6 as my diaper bag back when Ford was a baby :) You look so freaking comfy! Just a five minute ride is enough to put me to sleep…it’s so bad that I don’t even drive anymore :/

  9. Suzanne says:

    Woah!! Cat shirt!! I love this, Lisa, and you styled it so cute.

    I actually pinned this shirt a while ago but didn’t actually look at the shop. Definitely am now though! I’ll let you know if we end up twinners.. :)

  10. Suki says:

    Oh I adore that cat sweater! Also your travel bags are amazing :)

  11. This is perfect for road tripping or travel! I love every single piece in this outfit, but especially the etsy sweatshirt and the printed shorts! So adorable! You even have the roadtripping van back-drop! Happy Friday to you Lisa!
    xo Hannah

  12. Arielle says:

    That’s a bad-ass van! I love that sweater. This is a fun series!

  13. What an amazing sweater! Have a fun trip!

  14. Kimberly says:

    So cute. I just bought the kitty sweatshirt.

  15. Miki says:

    Awe, what a wonderful outfit, Lisa! ;P That sweater is awesome! Cats make everything awesome :p.

    And what a cool mother-in-law you have! I kind of want to meet her, hehe.

    Hope you have an awesome week! ;D

  16. Cara-Mia says:

    Cute outfit! I love road trips, although I’m not exactly the best companion either because I get so car sick. (I’m okay if I’m the one driving, though.) this reminds me it has been almost a year since my last trip. Boo.

    Anyway, have so much fun! Be safe. :)

  17. Marisa says:

    You truly make casual look uber cute Lisa! It’s funny because seeing this outfit reminds me of pieces in my own wardrobe and I now want to put together an outfit inspired by this :) I’m clueless when it comes to dressing more casually and typically for road trips wear yoga pants and a hoodie…hehe. xo Marisa

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