What’s the Deal With All Those ‘Flying Dress’ Instagram Vacation Photos?

After giving the popular Instagram trend a try, here’s what I learned.

Vibrant blue skies, charming architectural details, and a woman standing in a silky, billowing dress floating on air behind her, adding a splash of color to the landscape—chances are you’ve seen this image on your Instagram feed. Although the woman wearing the dress is radiant, she is only part of the scenery; the dress is the real star.

The flying dress trend started in Santorini. This photogenic Greek island is known for its picturesque whitewashed cliffside houses, which contrast with the stunning, blue-domed churches and the sparkling azure of the Southern Aegean Sea. The pop of a brightly colored dress with a 15-to-20-foot train flying behind the wearer makes the already gorgeous scenery come alive, and the effect is the stuff Insta-dreams are made of.

Today, you can find flying dress shoots everywhere, from cities to national parks to iconic landmarks like the Eiffel Tower. I’d always admired those flying dress photos, so ahead of a family vacation to Hawaii, I decided to see if flying dress shoots were a thing on Oahu. The answer was yes, and so I booked one. While I have zero regrets, looking back, there are a few things I would have done differently.

Pick a Day When You Don’t Have Plans

My vacation plans were already in place when I decided to book a flying dress photo shoot, so this was an add-on I had to fit into my existing schedule. I booked a sunrise shoot on a day when I’d planned an entire morning of exploring with my family. The meetup location with the photographer was about 20 minutes from my hotel, and when the shoot went a little bit long, my anxiety started to spike.

We’d made reservations to hike Diamond Head Crater, a popular hiking trail that offers a bird’s eye view of Waikiki. Diamond Head is so in demand that reservations and timed entry are necessary, and when my shoot went overtime, I became worried about being late and missing my hike.

Props to my photographer for taking her time and not rushing through the photo shoot, but if I could have a re-do, I would have shifted my plans so as not to feel rushed. Don’t be like me and instead, schedule your flying dress shoot when you have a free day.

Choose a Setting You’re Comfortable With

My flying dress photos were taken on a beach with black volcanic rocks. Looking back, I hadn’t fully considered how comfortable I’d be climbing on the rocks barefoot in semi-darkness while wearing what felt like a hot air balloon. My flowy purple dress had a lot of fabric, and when the wind got under it, I didn’t feel like I had great control of my footing, which proved stressful. My shoot was five months post-ankle surgery, so my footing and stability weren’t perfect. While I asked my photographer’s input on terrain and location, I may have downplayed my limitations and overestimated where I was in my recovery. 

Practice Makes Perfect

I’ve spent many happy hours binge-watching America’s Next Top Model and listening to Tyra and Miss Jay telling fashion hopefuls to “smile with your eyes” and “work your angles,” but I was never inspired to practice those moves in front of a mirror. If you’re a natural at posing and frolicking in front of the camera, swishing your flying dress might be intuitive, but that was not my case. My excellent photographer, Stacey, gave me some pointers on how to pose naturally that felt anything but natural. The finished product was great, but looking back, I wish I’d have taken some time to play with poses I liked.

Budget for Extras

The flying dress photo shoot usually involves a flat rate and an agreed-upon number of images. Your mileage may vary. Most photographers offer add-ons such as drone photography, hair and makeup, accessories, transportation, and the services of a dress stylist.

I regret not doing the drone shots, but I’m happy I paid extra to have a stylist on the shoot instead of taking my husband. She helped the photographer position the dress for shots, which doesn’t sound that difficult, but it’s both a skill and an art. The “flying” part of the flying dress shoot is integral to getting the shot, and having someone who understands how the dress needs to be fluffed makes everything run smoothly.

Prepare for a Total Lack of Modesty and Personal Space

Most of the flying dresses have an adjustable bodice to wear the dress in various styles. I was instructed to arrive in clothing I could slip out of quickly as well as to wear flesh-toned underwear. The photographer and her stylist helped me get changed on a public beach, holding towels up for modesty and wrapping the dress’s bodice in my chosen style. This happened about half an hour before sunrise, so the beach was still dark. There were a few people around, but I’m not sure if anyone was paying attention to naked me being pulled and tweaked into my dress. My photographer and her stylist were true pros, but it was a very up close and personal experience.

I knew I’d have to change on the beach, but I didn’t expect how the stylist would get up under my dress to help position the material for the shots. I don’t consider myself shy, but it was awkward having someone I’d just met hanging out under my dress with her face inches from my rear end. The fabric is so voluminous that you don’t see her in the finished shot, but next time you admire a flying dress picture, just know there’s probably a whole person swallowed up in that flowing skirt.

What I Got Right

I was glad I did the shoot early in my trip to Hawaii because I naturally got up early because of the time difference. I was also happy I opted to rent the dress from the photographer versus bringing my own, even though it was expensive  (I paid $250 to wear the dress for an hour). You can find flying dresses on Amazon for less, but they take up lots of space in your suitcase. As much as I loved my bright purple dress, it’s not something I’d likely re-wear.

While I find it difficult to associate the ethereal, dreamlike finished product with the rather stressful photo shoot experience, I don’t regret doing this for myself. It’s probably a one-and-done for me, but you never know—Santorini is still on my bucket list.