An Effortless Way to Plan the Best Outfit for a Road Trip [Step-by-Step]

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With so much to keep track of when planning a road trip, it’s easy to overlook your travel outfit. Yet, wearing the best outfit for a road trip is incredibly important.

You’ll need clothes that make you feel comfortable and, at the same time, allow you to arrive in style.

Find out how, below.

woman with hat beside red car | Enjoy Travel Life

CONTENTS: In this article, you will learn 7 steps to plan your road trip outfit. Find out the important comfort and style tips to easily decide on what to wear on a road trip, including:

  1. Wear Comfortable Footwear
  2. Dress in Stylish Layers
  3. Decide On Leggings, Shorts, or A Dress
  4. Bring a Big Travel Handbag
  5. Go Light on the Make-Up
  6. Sunglasses, Please!
  7. Tame Your Hair
  8. Final Thoughts

Your Step-by-Step Travel Style Guide

While travel time, season, and the route will influence your attire choices, follow these simple style tips to plan the best outfit for a road trip.

1. Wear Comfortable Footwear

The best footwear for a road trip is easy to slip on and off and isn’t too hot. Your feet can swell on a long ride (known as “hot foot”) so opt for lighter, cooler shoes that aren’t restrictive.  You’ll also want your footwear to be comfortable for driving and walking to explore an area when you stop—so definitely ditch the heels! 

When selecting the best footwear for a road trip, consider wearing one of these:

  • Flats: For women, flats are an excellent choice because they are light-weight and slip on and off easily. Flats also travel well if you’re packing light; some even fold up and come with a little pouch or traveling handbag. 
  • Sandals: Comfortable travel sandals or even flip-flops are also easy to take on and off, with the added benefit of breathability. 
  • Sneakers: Instead of opting for heavy athletic shoes or hikers, opt for comfortable, light-weight sneakers or tennis shoes for the drive. They are practical but look a lot neater, too. You can always throw your hiking shoes in the trunk if you’re inspired to explore.
  • Barefoot: If you’re a passenger, slipping off your shoes during a road trip offers maximum relief. If you’re the driver, that may not be a wise choice. Even though driving barefoot is not technically illegal, it’s discouraged because with bare feet, socks, or stockings, your foot may not have a good grip on the pedals. 
tennis shoes on beach | Enjoy Travel Life

Most importantly, make sure whatever footwear you choose as the driver won’t interfere with your ability to drive safely. 

And if it’s snowy or rainy, have boots with you. But you won’t want to wear them for the ride.

2. How to Dress in Stylish Layers for a Road Trip

No matter what time of the year you are traveling, the best tip for your road trip wardrobe is to dress in color-coordinated layers. For example, a typical woman’s outfit might layered this way:

  1. White Sleeveless Cotton Top
  2. Short-Sleeved Button-Down Blouse
  3. Comfortable Shorts or Leggings
  4. A Neutral, Light-Weight Sweater
  5. A Sheer, Colorful Scarf
  6. Dungaree Jacket

You can achieve the same effect by substituting a comfy dress then adding layers. 

If you’ll be making beach stops, you could wear your bathing suit (provided it’s not too snug) underneath it all.

Dressing in layers this way is a travel trick that offers the best climate control. If it is warmer outside or in the car, remove a layer; and if it’s chilly (or your driving partner likes to crank the AC), wear all the layers together.

For harsh weather, such as on winter road trips or rainy days, you’ll want to have the appropriate outerwear on hand for your layering recipe, like a warm coat, hat, and gloves or a rain jacket. 

Alternatively, you might wear a warm vest that provides extra warmth without feeling bulky or bring a blanket wrap.

3. Leggings, Shorts, or A Dress?

So, which is the most comfortable option for a road trip: leggings, shorts, or a dress? 

  • Leggings: If you are traveling during winter or spring, leggings are a great option. They offer comfortable coverage without being restrictive and transition nicely from casual to more dressy. They’ll also keep your legs warmer in cooler weather.
  • Shorts: Shorts are a perfect option to keep you cool and comfortable on a summer road trip. Draw-string shorts are especially comfortable because you can loosen them up as you ride.
  • A Dress: My favorite choice for travel is a loose-fitting cotton dress–the beachier the better for me. A classic shift is also a comfortable, versatile option if you’ll be stopping for a nice dinner and want a more formal look. Just throw on your scarf and flats and voila!

Men have fewer options but should look for light-weight, non-binding pants or shorts for the most comfortable ride. Linen slacks can offer a cool alternative to khakis, even though they might wrinkle easily.

At any rate, I recommend women and men avoid wearing jeans on a road trip because they are restrictive and bunch up. Personally, that would just make me cranky!

4. Bring a Big Travel Handbag

woman holding big brown leather handbag | Enjoy Travel Life

A large handbag is an essential accessory for a road trip. It carries all your necessities and puts them within easy reach. You can tuck in your phone charger, iPad, wallet, reading glasses, keys, travel notes, maps, pain reliever, and much more. 

I always keep my big leather bag from Italy with me in the front seat or at an arm’s length in the back, rather than packing these important items in my suitcase. That way I have easy access to them on the road. 

5. Go Light on the Make-up

I don’t normally wear a lot of make-up, and I think that’s part of aging gracefully. On the road, I wear even less. 

It’s a good thing because otherwise, I’d look like a racoon by the time I arrive at my destination…I have a tendency to rub my eyes on long drives. 

Plus, let’s face it: Make-up is uncomfortable. 

So, I go light on make-up for road trips of any length. Other than a little lip balm to keep my lips moist, I go natural for the ride—and it feels great! Not only is it more comfortable for my skin, it also allows me to splash my face with cool or hot water at a rest stop to freshen up. 

I’ll put on some mascara and lipstick once I reach my final destination, but no sooner. That way, I arrive looking fresh and neat.

6. Sunglasses, Please!

Whether you are riding a bike or traveling a car, sunglasses protect your eyes from the blinding sun or winter glare. 

You might splurge on some prescription or high-end sunglasses before your trip, or look for a stylish drug-store variety that offers added protection from UVA and UVB rays. 

Either way, wearing sunglasses is one of the best ways to hide your tired eyes and make you look cool.

7. Best Ways to Tame Your Hair

Envision yourself on a beautiful day, cruising down a scenic road with glorious fresh air pouring in your windows. Is your hair blowing in your eyes and face? How irritating.

riding free in car | Enjoy Travel Life

Instead, tie long hair in a bun, ponytail, or braid.  Or, keep those locks in place under a hat, bandana, or headband. Then you can really enjoy riding carefree on the highway.

Final Thoughts

Using these simple, stylish options, you now know how to put together the best outfit for a road trip.  You can be comfortable on your journey and look cute in photos while you’re making travel memories. 

What’s your go-to outfit for a road trip? Tell us in the comments below!

2 thoughts on “An Effortless Way to Plan the Best Outfit for a Road Trip [Step-by-Step]”

  1. 1, 2 and 6 are key for me. I get hip, knee and back trouble so shoes are key and I am sensitive to bright light! Great advice!

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