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Pinterest in Real Life: Travel Outfit

Pinterest in Real Life: Travel Outfit

For today’s Pinterest in Real Life, we’re talking travel outfits. I spent a few hours scrolling Pinterest looking for an inspiration outfit to work with and what I found was hilarious.

First, so many crops tops, with either sweatpants or jeans, as one does.

There were countless photos of influencers perched on top of their $10K suitcase wearing leather leggings and stilettos – AT THE AIRPORT.

Then there were the jumpsuits, the ones you have to pull down to your ankles when you use the restroom. I’m convinced these women have never actually stepped foot on an airplane. Yet here they are, taking their picture at the baggage check. God bless them when they have to pee.

Our inspiration outfit is from the blog Fashion Jackson in 2019 and the most practical of anything I could find. It’s a helpful reminder that with a few swaps, you can add practicality without sacrificing too much style.

Pinterest in Real Life: Travel Outfit

Airport outfit



Beach Sweater, $39.50 | Skinny Jeans, $68 | White SneakersCrossbody, $68 | Cat Eye Sunglasses, $55 

This is exactly what I wore on my flight to Florida last week. Whenever I fly I think about were we are landing. In this case, we flew out of Philadelphia around 7pm.  If we arriving in the morning, before check in, I would have worn some kind of maxi dress that could double as a cover up at the pool. 

But for this trip we were checking in after 10pm, so I wanted to be comfortable and casual but still well dressed. 

For this outfit, I used several familiar pieces. Our inspiration model is wearing what looks like a sweatshirt. I swapped it out for this J.Crew Factory “Beach Sweater.” It was a reader fave last month. Sizes are getting limited, but if you can grab yours do it. I wear mine frequently. 

It’s slightly sheer so you will want to wear a cami underneath. Another, not-so-sheer option is their cotton teddie sweater on sale for $17 in white in all sizes

Not everyone likes to wear jeans on a flight. I happen to prefer them to leggings, but only if they have a lot of stretch, like these by Wit & Wisdom. These are available in regular and petite (limited) and are great to buy now, wear now and later in the fall. 

Instead of Gucci mules, go with classic white sneakers. I love these by Cole Haan. Always try to wear your bulkiest items on the flight so you save room in your suitcase. 

The piece I was most excited to find for this look is this white quilted crossbody with a separate pouch for your phone. It’s not Chanel, but it’schic and practical and under $70. I picked it up in white and black for the fall. 

Finally, nothing screams casual glam like oversized black sunnies. Quay makes affordable options in a variety of styles. These cat eye sunglasses are at Nordstrom for $55


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Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

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Pinterest in Real Life: Travel Outfit

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Thursday 15th of July 2021

I keep watching this sweater to see if they restock medium in white. No luck. 😢 Such a cute look.

Lori Lee

Saturday 10th of July 2021

Love this and love the practical aspect of it as well. Thanks for sharing.


Friday 9th of July 2021

Great look ! I like Fashion Jackson. The pic, you said was from 2019. So I must ask, are skinny jeans still in style? What do you say?

Jocelyn Reid

Friday 9th of July 2021

Couldn’t agree more. Anytime I’m flying, comfort is paramount, especially on a long flight. A good friend gave me sage advice that I always follow: “Always wear sneakers or flats when flying. You never know when something could go wrong and you might need to run!”

Tracy Gray

Friday 9th of July 2021

Thank you for this post! For me trying g tod exude what to wear on a flight sometimes takes malinger than deciding what to pack. It’s perfect. Comfortable but perfect for looking good. Love it.

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