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What to Wear on a Road Trip – Outfits to Inspire You

By Sandra Roussy January 05, 2023 Beauty

Do you enjoy road trips? Road trips can be a great way to see and visit unexplored places and make new memories – either solo, with a partner, or with a group of friends.

Road trips can be a day trip to the neighboring town or a months-long cross-state (or country) journey. No matter what your road trip looks like, you need outfits that are comfortable and suitable for long hours of sitting in a vehicle and also be ready for possibly walking about. The key word is “comfortable,” obviously.

Here are our top road trip outfits:

  1. Denim Drive
  2. Pretty in Pink
  3. Dress for the Road
  4. Safari Ride

For my road trips, I like to wear clothing that has plenty of stretch, doesn’t wrinkle easily, and is versatile.

Here are a few outfit ideas to inspire you for your next road trip. I have linked the items in each outfit as a reference, but you can assemble these looks from items that you may already have in your closet. Let me know which one is your favorite in the comments below.

Denim Drive

Denim Drive

I love the total denim head-to-toe look. However, I don’t like to match the blue shades of the jeans’ bottom and jacket, so I make sure to break it up a bit.

Helpful tip: Make sure that your jeans have plenty of stretch and that they are not too small for you.

Match your denim with a long-sleeve (or short-sleeve, depending on the season) striped top and some red accessories. This is my all-time favorite go-to road trip look!

Find the items here:

Waist-Match™ Alina Skinny Jeans

Pima Crew-Neck Long-Sleeve Tee

Classic Denim Jacket

Woven Wool Scarf with Fringe

ECCO Sport Therap Lace Shoes

Pretty in Pink

Pretty in Pink

Maybe you are taking a road trip and will be stopping at a museum or having lunch somewhere nice? This pretty Audrey Hepburn-inspired look is perfect for those classy road trips. Cardigans and scarves are always great options when traveling.

Chico’s has a collection called “Travelers” which has a great selection of clothing made with wrinkle-resistant sustainable fabric.


Find the items here:

Travelers No Tummy Pants

Cashmere puff-sleeve cardigan sweater

NO IRON Stretch Shirt

Limited-edition Marie Marot X J.Crew silk scarf

RAY-BAN Sunglasses, EMMA 59

Washable Slip-on Flats

Dress for the Road

Dress for the Road

Stretch dresses are super comfortable for road trips, especially trendy sweater dresses. They look good with flats – and booties – and particularly good with riding boots.

Tip: You can choose to wear leggings or tights under your sweater dress for added comfort and warmth.

Find the items here:


Kenneth Cole Reaction Wind Riding Boot

LAUREN RALPH LAUREN Sparkly Reversible Knit Poncho


Safari Ride

Safari Ride

Convertible pants are great for all occasions and especially in variable weather conditions. Pants that can transform into shorts in a jiffy are great for road trips – no need to stop somewhere and find a place to change clothing.

This style of pants can easily be dressed up or dressed down depending on what you match them with and how you accessorize them.

Find the items here:

Craghoppers NosiLife Zip-Off Convertible Trousers

Chloe Cardigan


Dansko Booties

Animal Jacquard Wrap Scarf


Let’s Have a Conversation:

Do you go on road trips a lot? What type of road trip do you like to take? What’s your style when hitting the road? Tell us about it in the comments below.

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The Author

Sandra is the middle-aged woman you hear about who sheds everything she owns and sets out into the world to rediscover and redefine herself. After more than twenty years spent in the fashion industry designing collections for brands such as La Senza, Victoria’s Secret, and JACOB Lingerie, she shifted her path and pursued her longtime passion for writing, traveling, and photography. Sandra was published in the NY Times best selling book Eat Pray Love Made Me Do It. A deeply personal essay hand-picked by Elizabeth Gilbert about loss, facing fears, and going after dreams. Visit her website:

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