Travel days used to be the days I would put the least amount of effort into getting dressed, but because of my job as a travel creator and blogger and years of family trips, road trips, airports, and landing in beautiful places, I realized something: what I wear on travel days actually makes a big difference in how I feel.
Now I have a simple go-to travel outfit formula that’s comfortable enough for long flights and car rides, but still chic enough that I feel put together when we arrive at the destination. Whether we are heading straight to dinner, exploring the new area or taking photos along the way, I feel ready to tackle the day. It’s realistic, mom-friendly and built for travel days.
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If you have ever wondered how to look chic and stay comfortable while traveling, here is exactly what I wear on repeat for airplane travel and road trips.
Travel Day Outfit Formula
After years of traveling for a living: family trips, girls trips, long road trips, hours upon hours of sitting in airports and long flights, I finally figured out a simple formula for travel day outfits.
It’s comfortable enough to work on long travel days, but chic enough that I don’t feel like a hot mess in airport photos or when we go straight from arriving to exploring.
Here’s exactly what I wear almost every single time.
1. Start with Soft, Stretchy Base Layers
This is the foundation of the whole outfit. If this layer isn’t comfortable, then the whole day will feel uncomfortable.
I usually reach for:
- a fitted neutral tee or tank
- buttery soft leggings or relaxed travel pants
- a lightweight long sleeve undershirt if its cold
The goal here is soft fabrics, stretchy waistbands in the pants: nothing that will feel tight after sitting for hours. Comfort is key.
2. Add a Lightweight Layer
Even in the summer, I always bring a layer. Airplanes and airports are unpredictable, but most of the time I find them to be cold and nothing is worse than being cold on a long flight.
My go-to layers:
- a oversized cardigan
- a half-zip pullover
- a lightweight sweater
- a denim or lightweight jacket
I always try to choose something that looks cute draped across my shoulders or tied around my waist, more of a way to enhance your travel day outfit instead of taking away from it.
3. Choose Comfortable Shoes
Travel days usually mean way more steps than you think: airport security, terminals, rest stops…so wear comfortable travel shoes that still look chic.
I usually stick to:
- cushioned sneakers
- slip on mules or clogs for easy on/off in the car
- comfortable loafers
This is not the time to try out those brand new shoes. Nothing can make a travel day worse than painful feet.
4. Finish with Easy, Elevated Accessories
This is the step that will enhance your travel day outfit and take it from comfy to effortlessly put together. Accessories make all the difference.
My typical add-ons:
- a baseball cap
- oversized sunglasses
- simple hoops or studs
- a crossbody bag
- a neutral tote or weekender bag
These little pieces make such a difference and make your travel day outfit feel styled without sacrificing the comfort.
That my typical travel day outfit formula: comfy base layer, lightweight layers, comfy shoes, and chic, simple accessories.
Airplane Outfit Tips
Airport travel days are a little different than road trip trips. You have to deal with security lines, cold airplane cabins, & long walks between gates so comfort is key, but I like to feel put together when I land.
What I Avoid Wearing on Flights
- stiff jeans
- complicated layers
- belts
- anything too tight around the waist
Airport days are long and the goal is to feel comfortable from takeoff to landing.
Little Things That Make a Big Difference
- hair in a low bun or down (for comfortable napping on the plane)
- simple earrings
- oversized sunglasses for tired eyes
- a crossbody bag to stay hands free for boarding passes and rolling luggage.
Road Trip Outfit Tips
Road trip travel days call for a slightly different vibe than airport days. You are sitting for very long stretches, hopping in and out of the car and driving. You want to be comfortable, but still cute for the stops to eat and photos at those scenic pullovers.
Favorite Things to Add to My Road Trip Outfit
- a roomy tote with snacks, wipes and chargers
- sunglasses
- comfortable slip on shoes
- a claw clip or hair tie
- a lightweight sweater
My Go-To Cold Weather Destination Travel Day Outfit
Cold weather travel days take a little more strategy. You may be leaving your destination in mild weather, but may be snowy where you are going, so you have to think about staying warm once you land.
I have found when traveling to a cold weather destination, layers are everything.
Typical Cold Weather Travel Outfit Musts
- a warm base layer: fitted long sleeve tee or thin thermal top
- leggings, chic sweats, or ponte pants
- cozy sweater or cardigan
- packable puffer or wool coat
- comfortable boots or weather friendly shoes
Cold Weather Travel Day Tips
Wear your heaviest pieces on the plane to free up luggage space.
Bring a large scarf or wrap. It can also double as a blanket in flight.
Stick to neutral layers so everything works together if you need to add or remove pieces.
My Go-To Warm Weather Destination Travel Day Outfit
Warm weather destination travel days are a little easier to dress for than cold weather destinations, but comfort still matters just as much. The goal is to stay cool, avoid anything clingy and still feel cute when you arrive in the warm weather.
Warm Weather Travel Day Outfit Musts
- breathable, relaxed pants: linen pants, lightweight wide leg pants, stretchy ankle length pants
- tank or soft tee
- lightweight button down or layer
- comfortable sneakers, slip on shoes or sandals
Warm Weather Travel Day Tips
Sunglasses instantly elevate your outfit
Put hair in a low bun, braid or claw clip, especially if traveling to a humid climate
Pack a mini freshen-up kit: travel deodorant, facial mist, lip balm
Chic Travel Sets: The Easiest Way to Look Put Together
If you want to look instantly polished on a travel day without having to put much thought into it, matching travel sets are the answer. This has become one of my favorite travel day outfit tricks because it feels like loungewear but looks put together.
A good travel set is comfortable enough for long flights or road trips, but structured enough that you can walk straight off the plane and into a coffee shop, restaurant or explore without feeling underdressed.
What I Look for in a Travel Set
- soft, stretchy fabric that doesn’t wrinkle easily
- a relaxed, but flattering fit
- pieces that can be mixed and matched later on the trip
- sets with wide leg pants, joggers or pull on trousers
Here are the travel sets I reach for most:
A Knit Lounge Set: a soft knit pullover with matching wide leg pants or joggers. This is perfect for cooler travel days.
Half-Zip and Matching Pants: a lightweight half zip with coordinating joggers or straight leg pants is a great go-to.
Short Sleeve Top and Travel Pants Set: For warm weather trip, I love a soft matching short sleeve and relaxed pant moment.
How to Style Sets So They Don’t Look Like Pajamas
- cute, elevated sneakers
- a structured crossbody bag
- sunglasses
- baseball cap
- simple jewelry
My Travel Day Bag Essentials
A good travel bag is key to elevating your travel day outfit. For airport travel days, my go to travel bag is the Calpak Luka Duffel Bag. It fits under the airplane seat with ease, wipeable fabric and roomy for all of your travel day essentials. For road trip travel days I prefer a tote bag for easy access while I’m in the car.
Inside my personal item you will always find:
- lip balm
- hand cream
- portable charger
- snacks
- wet wipes
- hair tie/claw clip
- hairbrush
- mini deodorant
- breath refresher
- hand sanitizer
- headphones or earbuds
Find all of travel bag essentials HERE
Before Your Next Trip…
Travel days don’t have to mean sacrificing comfort or style, you can have both. Having a simple travel day outfit formula makes packing easier and helps you feel confident from takeoff to arrival.
Save This Post for Your Next Trip
Bookmark this post or pin it so you can come back to these outfit formulas the next time you’re packing for a trip.
Shop My Travel Day Outfits & Essentials
I’ve added everything in this blog to a travel day outfit collection to make it easy to recreate all of these travel day outfits. Shop everything from this blog post all in one place HERE.
Travel days are the start of the adventure. Start your vacation off right! Happy travels.
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