Chic & Comfy Road Trip Outfits [+9 Packing Tips!]
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You know the feeling you get when you nail the assignment – when you pack perfectly, are comfy and chic on your road trip, when the 3 tops and 2 bottoms you brought somehow coordinate to make at least 16 outfits when you get that “WoW” look of appreciation (and dare I say jealousy) from your partner because they see you only brought a small bag for the week.
I’ve been a full-time digital nomad and traveling out of a carry-on suitcase & a small backpack for 4 years now, and I sometimes impress myself with the amount of shit I can get in my bag, as well as my strategy for what to leave behind. And dare I say, I still look cute on my road trips!
This may be my over-maximizing brain talking, but I get such a kick out of thinking what and how to pack, especially when it comes to comfy road trip outfits. I’ve been perfecting this strategy for over a decade, so here I am, sharing all my secrets!
9 Tips For Packing Comfy Road Trip Outfits
Here are my best-kept secrets to packing in only one carry-on bag!
1. Bring Comfy Shoes
Sneakers are your friend for those long hours on road trips. Some people prefer flip flops or those little ballet flats, but I find the most versatile is a nice, clean, white sneaker – mostly because I’ve appreciated closed-toe shoes for some questionable gas station or nature bathroom situations.
Oh and limit yourself to 2-3 pairs of shoes max – one sneaker, one nice option for going out, and one sandal option.
2. Get a Good Road Trip Bag
After owning a few small bags and many more backpacks, I’ve settled on my favorite Timbuk2 Wingman Backpack for a long weekend road trip. It makes a getaway easy; it’s super well-compartmentalized and has a clean design.
And because the carry-on has become the new backpack these days, my go-to is the AWAY carry on bag with the packing cubes (the link gets you $20 off – a must!).
3. Roll Everything
I fit loads of cute road trip outfits in my bag by rolling everything. It just makes more sense architecturally.
Oh! And don’t forget to stuff smaller things into your shoes – panties, gym clothes, bathing suit, socks, etc.
4. Pack Wrinkle-Free Clothes
To keep you looking stylish in photos, don’t bring fussy clothing that requires ironing.
This might mean you’ll have to leave your favorite organic cotton maxi dress behind – natural fibers tend to wrinkle faster.
5. Think Layers
I recommend packing a favorite graphic tee, tank tops, a light denim jacket, and a long sleeve sweater that can be layered to keep warm as needed.
Plus, layers lend to more outfit inspiration as you mix and match all the travel clothes.
6. Limit the Tight Stuff
Road trips mostly happen in a car, so leave the skinny jeans at home for maximum comfort.
When I say, “limit tight stuff”, I am NOT including black leggings in this category, as they are critical for those long drives and are a good option for any body type on long drives – plus they go with everything!
7. Neutrals + Splash of Color
For maximum mix-and-match options, pack different neutral colors (nudes, whites, blues, grays, blacks) but don’t be scared to include a couple of bold statement pieces or prints. There’s no need to be boring just because you’re going for a casual look on the road!
8. Don’t Forget Your Tech
This means chargers, headphones, a laptop (for when you need to watch that late-night movie), converters if you’re jumping countries or battery packs.
9. Go Lean on the Toiletries
Get a small makeup bag, and limit yourself to anything that fits – a must is a toothbrush, travel-size toothpaste and shampoo, hand sanitizer, chapstick, small sunscreen, wet wipes, and hand lotion.
I find if I limit myself to a small makeup bag (and don’t cheat), I am better at being lean on what I pack.
How can I look stylish when I’m traveling?
Before we get into the checklists and cute road trip outfits, I want you to really internalize that less is more for long road trips.
To that point, I personally lay out everything I want to take based on the checklist below, and then… I cut that in half. And the remaining half is what I take on the road. I know, it’s dramatic, but at the end of the day, this trick works.
What should I wear on a long car ride?
Sneakers – I love my white Chuck Taylor Converse, they go with everything and are super comfy. After a few wears, and scrubbing them down with shampoo and a little brush, they have the perfect vintage look.
A Pair of Leggings – Invest in these Athleta Ultra High Elation Tights and never look back. They are super soft and stretchy, they tend to run a little bit big, and feel like silk to the touch.
Sunglasses – While some girls bring floppy hats to protect themselves from the sun, I find them a bit too unwieldy. I opt for a pair of sunnies for any road trip.
A scarf – Can be used as a pillow, if the AC is blasting too high in the car, a wrap, and is even a great option for a beach towel if you get desperate.
A jacket – I take my Columbia Splash Side Jacket with me on all my trips because it’s lightweight, warm, packs super small, acts as a wind and rain jacket, and is that special pop of color I need for Instagram selfies. That said, a light denim jacket works well too!
Waterbottle – I’ve had a few, but my favorite brand that keeps for a long time is Columbia Double Wall Waterbottles. You can see mine in the picture covered in travel stickers.
Small Backpack – Or a large handbag, whatever your preference. Depending on the destination of your road trip (and length), you may want to add a few things to that bag.
Bathing Suit – My favorite brand is L-Space Swimwear because the cuts are so flattering for curvy women like me! And if you have one of those reversible swimsuits, even better!
Toiletries bag – Travel-sized everything, including lotion, toothbrush, wet wipes, hand sanitizer, a mask, chapstick, a little handheld mirror, and maybe a small comb. Don’t bring all your hair products or the full set of face brushes – think bare minimum, not “just in case”.
Your Tech – Headphones for when you want to zone out, listen to your book, etc. But also your charger, laptop, or any other gadgets you love for taking photos and making memories.
What are the best travel outfits for planes?
Everyone has a strategy for long flights – from wearing your bulkiest outfit so you can fit more stuff in your carry-on to wearing your PJs for ultimate comfort.
I subscribe to neither of those camps, rather I like traveling light. This is why I recommend something similar to the comfy road trip outfit from above, with these additional DO’s and DONT’s in mind for flights:
❌ Don’t wear heels. Or shoes that are hard to take on/off during security checks.
✅ Do keep accessories to a minimum. This includes belts, watches, and jewelry that might ring an alarm – again if you want to pass through security fast, keep it simple.
✅ Do keep it organized. Make sure to have your toiletries bag and laptop handy and organized so you can remove these quickly for security checks.
Comfy and Cute Road Trip SUMMER Outfits
Here are my mini capsule summer road trip outfits for a weekend trip somewhere warm. I’m using my summer on the Coast of Croatia Road Trip as inspiration for these outfits!
2 Summer Dresses
1 Pair of shorts + 3 of your favorite tops
1 pair of comfy sandals that work with the dresses, but are also great for the beach!
1 Pair of white sneakers for walks/treks but also cute with your more stylish travel clothes (ie. dresses and tops)
1 Bathing suit
1 Summer Scarf that can be used as a beach towel or at night if it gets chilly
Undergarments + 1 Sportsbra
Sunglasses
Makeup – mascara goes a long way. So does one tube of tinted chapstick.
Travel Size Toiletries – sunscreen, face lotion, deodorant, toothbrush, toothpaste, wet wipes for when you need to clean up real quick
Chargers & your travel tech gear (cameras, selfie sticks, etc)
Comfy and Cute Road Trip WINTER Outfits
Now for the counterpart, a mini capsule wardrobe for a weekend in cooler weather. This time, I’m using my South Norway Road Trip as inspiration – these are great for the fall and winter seasons.
1 pair of boots
2 Thermo undershirts/underpants instead of regular cotton shirts – I highly recommend UNIQLO thermal gear.
Instead of a pair of cargo or winter pants, bring a pair of leggings and/or a pair of jeans- wear the tights underneath your jeans or double them up for extra warmth. Oh, and don’t forget you can stuff those leggings in your boots to save space.
For coats, consider 1 down jacket instead of wool or military jackets. If you use a compression bag, down jackets will pack ridiculously thin! Plus they tend to be lighter than other types of jackets.
Scarf, gloves, winter socks, hand warmers, and a cute warm hat.
Sunglasses – there’s still sun in the winter, and snow on the ground can cause a whiteout – you’ll need those sunnies to protect from the brightness!
Undergarments + 1 Sportsbra
Travel Size Toiletries – prioritize sunscreen, face lotion, and chapstick. But don’t forget the deodorant, toothbrush, and toothpaste.
Chargers & your travel tech gear (camera, selfie sticks, etc)
And if all Else Fails, Remember This!
You can always buy what you’re missing along the road. In fact, I love to buy jewelry/accessories and graphic tee’s along the way as cute wearable souvenirs and additions to my comfy factor for the open road.
Bon Voyage my friends, I’m hoping you now feel more equipped to pack like a rock star for your next adventure!
