What to Wear on a Road Trip Across the Country

When I started packing for our cross-country road trip last month, I’m not gonna lie: I started to panic a bit.  Figuring out what to wear on a road trip can be so stressful!  Especially if you’e going to be gone for a while.  

We spent 3.5 weeks on the road, had our items shipped from Virginia to California, and our belongings are still in storage for a couple of weeks before moving into our new apartment. That meant that I had to pack for 7 weeks on the go, and I only could carry one checked luggage and one carry-on suitcase.

One thing about traveling cross-country: you’re going to come across various climates along the way. We went from Kentucky, which was rainy and in the 60s, all the way to Las Vegas, which was 100 degrees. That being said, packing became a little tricky with all of the weather conditions we endured.

So: how do you pack for several weeks on the road with varying temperatures? I’m no minimalist, but here’s what I’d recommend bringing!

What to Wear on a Road Trip

Cozy Cotton Dresses

If there’s one thing I reached for over and over again during this road trip, it was my cozy cotton and t-shirt dresses. They’re comfortable enough to wear on long car rides — I wore the dress pictured above for our longest stretch, which was 10 hours of driving. These dresses are also effortless to layer and look perfect with comfy shoes like sneakers or sandals.

My friend Dana hooked me up with this dress from Lou and Grey dress last summer, and it’s the perfect piece to throw on and go. While this particular style is sold out, I would recommend looking for a dress in Lou & Grey’s Signaturesoft fabric. It is the coziest fabric I’ve ever put on my body, and you really can’t go wrong with it!

Shop My Favorite Cotton Dresses:

Bike Shorts

I know, I know…this is a controversial trend. But in my opinion, bike shorts = summer leggings.

I packed multiple pairs of denim shorts for this trip. Guess how many times I ended up wearing them? I can count the number on one hand. Bike shorts are super comfortable, on-trend, and believe it or not: you can dress them up and down pretty easily.

I wore a pair of Aerie bike shorts on Day #1 of our road trip, and I stayed cool and comfortable throughout the 8-hour drive. I love bike shorts because they rarely ride up, prevent chafing, and are great to layer underneath tunics or dresses that might be on the shorter side. I was shocked at how much use I got out of them, and I plan on scooping up a few more pairs from the summer.

Shop My Favorite Bike Shorts:

Denim Jacket

I packed two denim jackets on this trip, and they were the MVPs of my suitcase.

Once you get out west in the desert, it’s super hot during the day but chilly at night. Or, if you’re going to San Diego in May or June, it will probably just be a bit on the cold side. I throw a denim jacket in my car at all times when I’m in California because if you drive 30 minutes towards the coast, you can easily experience a significant drop in temperatures. Plus, they’re easy to layer over those cotton dresses and bike shorts.

Shop My Favorite Denim Jackets:

Rented Clothes

If you’ve followed me for a while, you know that I love wearing dresses and printed pieces. However, many of the dresses I have aren’t the most versatile pieces, and maxi dresses take up a ton of space in the suitcase.

When I was packing, I only packed dresses that I could wear in a few different ways. Dressed down for travel days, dressed up for a dinner out. If I couldn’t wear it more than one way, it went into storage.

Because I packed mostly the basics, I decided to rent clothes for a bit of flair and variety during this road trip. I reactivated my Rent the Runway Unlimited membership, which I admittedly canceled at the beginning of the pandemic, and I was pretty happy with the results. They did change it from purely unlimited to a limited number of slots per month, but honestly, even at the top tier of the membership, I didn’t get through all of the slots I had available in a month.

It was easy to ship items to my hotel on the trip, and since I was driving, I’d drop off my package at a FedEx store once I was ready to swap out for new items. I loved having the variety, and I also loved not having to wash the items — because, let’s face it, dirty laundry adds up quick when you’re on the road.

Do you have any extra tips about what to wear on a road trip?  Let me know in a comment below!

Photos by Tom McGovern