How To Stay Stylish While Traveling


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Back in the day when flights were first introduced, traveling by air was somewhat of a status symbol. The who’s who donned their “Sunday best” outfits for flying, as it was considered a grand occasion that one had to dress the part for. Fast forward to the present time, not as much importance is placed on being dressed to the nines while traveling. However, there are still some of us who like to make an effort to look put-together.

Howdy friends! Hands up if you like to dress comfortably while traveling, but are not willing to compromise your sense of style to do so. Can I hear an Amen? *Pentecostal handwave* But who said comfort is synonymous with being unstylish? It’s lies, I tell you, all lies! If you’ve been seeking ways to amp up your travel style, you have landed on the right online doorstep. Come on in, and join us on this travel style journey. All that’s required is your unique style passport and boarding pass. Are you ready? Let’s go!

We subscribe to the notion that dressing well is a form of good manners. It’s not meant to be a nose in the air statement, but rather a statement that speaks to the fact that we take pride in our appearance. Don’t be that person who runs into someone you know at the airport, and you’re forced to use the “I don’t always dress like this” disclaimer. *chuckles*  You really don’t have to go overboard with your travel outfits. The following are a few outfit ideas that are simple to implement. Let’s start with the ladies, why don’t we?

  1. Sporty

I love heels as much as the next ultra-feminine lady; however, some days I couldn’t be bothered to wear them. Case in point, when traveling. Can you imagine hobbling across terminals in stilettos, while hauling heavy luggage? Ummm no, thanks.  Give me a comfortable pair of shoes, please and thank you! Remember, we’re staying stylish, but comfort is key. That being said, you can still be creative with the type of footwear you don. For this particular look, I opted for a pair of animal print sneakers. It was an unexpected addition of sass and spice to a relatively casual outfit. The sneakers are lace-ups but, they are easy to get in and out of without the need to untie the laces. Convenient, for getting through airport security lines, right?


I wore the denim jacket because I typically need some type of jacket/sweater while airborne, even in warmer months. I don’t tolerate high altitude temperatures too well, even within the confines of a pressurized cabin.

I don’t know who sits on the style replay committee, but I’m so glad they brought back bodysuits from the ’90s. I love that they are so readily available now, and we have such a wide selection to choose from. Opting to go with a bodysuit for this look was a no-brainer. Who wants to deal with unraveled shirttails when you can slip into a bodysuit for a sleek look?

Winter, summer and everything in between, you will catch me in all manner of hats. They have to be one of my favorite ways to accessorize an outfit. For this look, I opted for a wide-brim fedora hat.


  1. Preppy

I love blazers, any day, anytime, anywhere. There’s just something about them that is quite spiffy.  Given that we are smack bang in the middle of summer, I opted for a lightweight blazer. Pssst (*whispers* it was originally long-sleeved, but I DIY’d it and made it three-quarter sleeved so I could wear it in warmer months.)  Back to the matter at hand…

I’ve always been a sucker for the prep school-inspired look. Give me a tailored blazer, cigarette pants, and a pair of loafers and I’m set! Bringing preppy vibes to the skies is the name of the game! For this look, I chose a white, lightweight blouse with a bow neck detail to simulate a necktie. The ultra-comfortable loafers have a slightly elevated heel, which I’ve heard is better for your back than a completely flat heel. Loafers are also easy to get in and out of, making them an obvious airport/flight footwear choice.

The structured box purse added an extra layer of class, and the wide-brim hat completed the ultra-chic, miss dapper look. You’ll notice that I didn’t wear much jewelry, opting only for one of my trusted wood watches. This preppy look is simple to put together, elegant and airport ready for all seasons. In colder months, just throw on a coat and you’ll be good to go.


I tend to steer away from dresses and skirts while traveling, but I found ways to still create girly looks.  On that note, nothing screams girly like a floral print. Add to that a flowy kimono and you have the ultimate feminine look. One of the attributes about kimonos that I love is their versatility. You can throw them over any outfit and immediately take an outfit to finger-snapping slayage levels! Plus, kimonos are always vacation-ready. Once you land at your travel destination, you can trade jeans for a pencil dress, shorts, etc, throw your kimono over the look and start your vacation off with a bang! For this look, I paired the kimono with a tank and high waisted jeggings for a sophisticated but comfortable look.

Remember I said I would never travel in stiletto heels? Yes, that still stands. However, I am not opposed to wearing block heel booties while traveling.  I’ve found that the right pair of shoes can take an outfit to a higher style level. This look with flats would have been casual, but with booties, it’s been elevated to sophisticated status. For extra comfort, slip gel inserts into the shoes and you will be guaranteed a lovely foot experience throughout your journey.



For the Guys

You didn’t think we forgot about you, now did you? I think it’s safe to say that most guys would rather not travel in a full-on suit, yes? For the purpose of this post, our focus will be on the comfortable, stylish dapper outfit choices.

Breathable cotton t-shirts and jeans are always an easy option. If you’re concerned about possibly frigid cabin temperatures while inflight, consider carrying along a lightweight jacket or jumper to don when airborne. For a more preppy look, throw on a tailored blazer and you have a well-put-together dapper look.

Nothing speaks vacation-ready like white on white outfits. Just be careful with drinks offered on the flight. We wouldn’t want that cran-apple juice to spill all over your outfit during turbulence. If you’re concerned about how to keep your whites white, choosing a “safer” darker color is perfectly alright.

When it comes to footwear, sneakers, loafers and boat shoes are always a comfortable style choice. We steer away from flip flops or any other open-toed shoes while traveling primarily for style, but also for hygiene reasons. Airports and planes are some of the dirtiest places. Our feet being hosts for germs is not how we roll.

Sunnies while traveling? Why, yes! Don’t mind if we do!  We keep ours on during flights so the flight attendant can think we are awake during snack time. 😀  No really, sometimes when flying in the day time, passengers may have their windows open. We wear sunnies to protect our eyes from the sunlight. Oh and to be cool too. No shame in our game. 😉

In conclusion, travel styles do not have to be over the top. Keeping it simple is actually ideal. The key is to choose one statement piece that can transform an outfit from basic to vavavoom!  Take pride in your appearance at all times, even while traveling. *gets off soapbox*

Our travel outfit choices are constantly evolving; therefore, best believe we’ll be back with more in upcoming posts. Meanwhile, we’ve shared links to either the exact or similar outfits showcased in this post.

You can shop the outfit details below, but first…

Disclosure: This post contains affiliate links. At no additional cost to you, I earn a small commission on items purchased via the shared links. This allows me to continue to purchase more stylish pieces that I showcase on this blog.

Now back to shopping…

Sporty Look



Preppy Look


Girly Look




Guys Looks


It is our hope that we have inspired you to stay stylish even while traveling. Did we succeed? Now go forth and be dapper!


22 thoughts on “How To Stay Stylish While Traveling”

  1. You two are adorable! I love all of the fashion ideas: I would sport those anyday

    • Aww thank you so much!

  2. I’m guilty of bringing “comfortable” clothes when we travel vs. fashionable. But I can probably have the best of both worlds!

    • Yes, the best of both worlds is so possible!

  3. I like your style! it’s sporty and casual but elegant. You do have it all together. I too remember the days when we traveled all dolled up. So stressful, glad those days are gone.

    • Thanks so much for the great feedback.

  4. Loved the different looks, especially the sporty one. The big wheels make it easier to pull on uneven sidewalks.

    • Thanks so much. Glad the style resonated with you.

  5. very cute outfit looks! its hard to pack only so much in one suitcase

    • Thanks a bunch! THe secret is to pack a few statement pieces and pair them with neutrals.

  6. I love the creative video you put together! It is so much fun.

  7. It’s so tempting to go with comfy, but it looks better when you land if you’re comfy and stylish too. I love the length of the jackets.

    • Yes, you can be comfortable but stylish. Thanks for the feedback.

  8. You look so so stunning! Love the outfit on you, it really works for you. Thanks for the post.

  9. You both look super stylish and oh so ready to conquer the air! We fly a lot as a family and as you say, not many people make the effort to dress up when they are travelling as its so common now.

    • Thanks so much for the lovely compliment.

  10. I absolutely love both looks- stylish yet comfortable too! A perfect combo when traveling and you nailed it!

    • Thanks so much for the great feedback!

  11. A couple that styles and travels together stay together. I love all of the looks!


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