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7 Cute Road Trip Outfits to Wear

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7 Cute Road Trip Outfits to Wear

Looking for cute road trip outfits to wear on your next getaway?

I’m a big fan of road tripping, though I am typically the passenger who gets to sleep half the time 😛

I’m all about comfort when it comes to road trips – it just ain’t fun sitting in the car for long hours in tight jeans or knee-high boots.

Also, you want to make it easy to run out of the car and pee if you have to, ya know?

Okay, maybe you don’t know if you haven’t been on many road trips, but boy oh boy – when you need to pee, you need to pee.

If you’re looking to plan outfits for an entire trip, I’ve also got a blog post all about how to plan your travel outfits so you can look cute and photo-ready the entire time.

Here are some cute and comfy road trip outfits you can wear on your next getaway!

Be sure to also follow me on Instagram – I share a lot more content on there that doesn’t make it to the blog!


Cute road trip outfits to wear


Hike at Mono Cliffs Provincial Park in Orangeville, Ontario

Tee + denim shorts

Probably my go-to road trip outfit during the summer is a simple tee and denim shorts.

It’s just super easy to throw on, and it always looks good!

All about dat capsule wardrobe, y’all.

Definitely don’t wear denim shorts with a button fly and don’t wear ones that are too tight.

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I also love keeping a plaid shirt tied around my waist ’cause it adds a little somethin’ somethin’, and it’s easy to throw on if it gets chilly.


Hawaii outfit - Aritzia straw hat, Zara mini dress, Fjallraven Kanken mini backpack

Mini dress

What’s more comfy than not wearing pants?

A cute mini dress is another one of my go-to summer road trip outfits.

It’s especially nice on hot summer days to let your thighs breathe.

Throw on a cute straw hat to spice up your look for photos!


Samuel Wilmot Nature Area in Newcastle, Ontario

Maxi dress

Maxi dresses are also super comfy to road trip in, especially if they’re loose and flowy.

It’s a terrible habit, but I love crossing my legs while in the front seat, and maxi dresses make it easy.


Chedoke Falls, Hamilton, Ontario

Tank + leggings

Sometimes you just don’t want to wear an “actual” outfit, ya know?

If you’re doing hikes along the drive, it’s definitely the most comfy to throw on a tank or sports bra and leggings.

It doesn’t even have to be a boring outfit – go with a cute matching set and bam, you’re photo-ready!


Summer hiking in Long Sault Conservation Area, Bowmanville, Ontario

Matching workout set

I absolutely adore matching workout sets, especially if they’re bright and colourful.

It’s a super comfy outfit to wear on your road trips, and it’s especially great if you plan to do some hiking stops along the way!


Queen's University Belfast, Ireland

Denim on denim

As a Canadian, I love wearing denim on denim (AKA the Canadian tuxedo).

It’s a chic outfit you can wear to explore the city or make stops out in nature!

Just don’t wear tight jeans if you’re road trippin’ – unless you want to have your pants unbuttoned the entire car ride.

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Reynisfjara Black Sand Beach in Vik, Iceland

Sweater + jeans

When visiting colder destinations, a comfy sweater and jeans is always my go-to outfit.

I usually pack multiple sweaters and wear the same jeans the entire trip!

You can even just wear the same sweater everyday ’cause you don’t really sweat much in colder places.


Cute road trip outfits:

  1. Tee + denim shorts
  2. Mini dress
  3. Maxi dress
  4. Tank + leggings
  5. Matching workout set
  6. Denim on denim
  7. Sweater + jeans

These were some cute and comfy road trip outfit ideas for ya to wear for your next getaway!

What do you normally wear on road trips? What are some other cute road trip outfits to wear? Let me know on Twitter or Instagram!

P.S. if you liked this post, you might like this post on how to plan your travel outfits, or any of my other posts on travel tips.

Be sure to keep up with me on InstagramTwitter, Facebook, and Pinterest if you aren’t already!

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Jessica Lam | Toronto lifestyle, fashion, beauty, and travel blogger | Diary of a Toronto Girl, a Canadian lifestyle blog

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