Romanticizing Airport Style


As I finish packing for a long-time-coming trip to Italy with family, I am busy with finessing my bags, double checking my various lists, and contemplating adding another layer to my flying outfit: shall I add another jacket on top, si or no, mi amore?

Seeing the end of preparation phase in close sight, my brain has been flirting with the state of airport style. Whilst (I’ll pause for your groans) the golden days of suiting, dresses, hats, and gloves were well before my adult years, I do want for it. Or at least a version of it. While I know it’s silly to want something from the past - especially when it wasn’t a common experience for me or my parents – I do romanticize. How fabulous would it have been to be surrounded by other travellers in a version of their sartorial best?

Nostalgia could be added as a new resume skill set for me. I’m the person who starts missing the event while still in said event. The word “mindfulness” and phrases like, “Being present in the moment,” are so outside of my current prowess that they are, in fact, borderline triggering. When I’m on a lunch out with a friend and the food arrives to the table I sometimes think, “Oh this is going to be over soon.” Same goes for a concert or show. Halfway through I start to get a little bummed about its forthcoming end. Time is a fickle, yet real construct for me. As soon as the June summer solstice hits, the very next day my gut sinks a bit as I know the long days are dwindling. Healthy perspective to hold: no. My reality: si. Let’s say it’s more instinctual for me to be in next, next, next mode then it is to just be, be, be. I guess that’s why I want people looking and feeling their version of best.

When I go through airports, it’s very common to notice the juxtaposition of the staff in crisp uniforms and the travelling customers in “comfies” or “cosies.” I’m not here to judge or shame – as always, do you when it comes to dressing – but I would be lying if I hadn’t fanaticized about what others would wear should it be another time or place. Sure, there are plenty of business travellers that have their look on lock – George Clooney’s character sharing all his carry-on secrets with Anna Kendricks character in Up in the Air comes quickly to mind – but what about others? I sometimes use the imagination framework of this question, “If you were the lead character in your own movie, and you had just one flight scene at airport, what costume or wardrobe would you love to wear?” Of course, it could/ would/ should be influenced by what your action is, perhaps its running towards a loved one after time apart, maybe you’re having a deep chat and a tall drink at a bar, or maybe you’re a new Canadian just arriving to your new home. Ah, I love a good roll play.

So, tell me your action and then tell me what would you wear?

Next question, when in a similar scenario IRL, are you wearing it?

Why or why not?

I heard Kelly Ripa say as a guest on a podcast that should she ever be in an accident where she was rushed incapacitated to the hospital, when they swap her over to a medical gown, she’d hope that staff would think, “Well, she’s put some effort in. She tried.” when unrobing her. Dark yet effective. Personally, I much prefer that hospital setup then other scenarios like dressing for if you should bump into an ex or colleague. Plus, I’m morbid AF so an unconscious at hospital is a bit of a buy one, get one imaginary situation that I find highly satisfactory.

Coming back to airport style, when I fly my general strategy is as follows:

  • On my person is many, many layers suitable for the weather of my destination and it’s almost like another charge free carry-on bag. I shove so much shit in my pockets I could moonlight as a counterfeit watch salesperson in Central Park. I usually pack a foldable reusable thin nylon bag should my destination be dramatically warmer than the flight and I need to shed some layers. Pretty rare but it does happen. Most of the time I revel in the rare occurrence that I am warm.

  • I typically choose a look that I’d be okay to die in. Also a simple hack to share, what I fly there in, I fly home in that very same look. My partner and I will ask each other, “What are you flying in?” as part of our preparations.

  • As I trust literally no one in this fine world – giving big Enneagram 8 energy - so all valuables are carry-on. There’s no jewelry in a checked bag, nor is there medicine, nor is that one outfit I for sure need. I pack with the assumption that any checked bags will fall off the edge of the airport and via a UFO helmed by Kate McKinnon, blast straight into space never to be seen again. It’s fun for me to think about just how far into space my Air Tag will successfully track that checked bag. Should the checked bag arrive as planned, it truly is a delight. When I hear folks saying they like to be on the plane as hands-free as possible I immediately worry for them and then attempt to turn on my empathy hat and refocus my thinking to how freeing that might feel. But, honestly, I mostly worry.

  • No exposed legs, torso, or arms. Flying is so cold and I dry heave and full body wince at the thought of bare skin grazing anything near me.

  • I wear the most cumbersome shoes on the plane. Whether that’s my high heels or combat boots. When I get settled into my seat, shoes come off and high legged wool socks go on.

  • Post socks, my eye mask is on, my scarf goes around my head, and I try to sleep as much as possible. The added bonus of my head gear is that people get the visual that they should avoid labouring to talk to me. I drink my own water and rarely accept the food offered. I’m a stay-in-my-seat for up to a three-hour flight. At my utter personal annoyance, I accept that longer hauls require a biology break or two.

  • My outside layer – jacket, sweater, overcoat – drape over my legs as my blanket.

Now I’m ready for snoozeville. Population: me.

Am I ridiculous? Perhaps, but travel is zany enough as it is. I’ve found comfort in removing easy-to-predict-trainwreck-like obstacles where I can: the packing. Then I can truly get as close to relaxing as possible for high strung little ‘ol me and roll with whatever experience is sent my way and looking just the way I want while doing it. I’ll have the Instagram Stories to prove it.

Arrivederci!

You turn to share: what’s your go-to airport or plane outfit? Any packing hacks to share?


Are you onboard this travel train and want more stops? Choo choo, I got you, boo. Check out other packing and travel themed More To It posts below…

West Jet and Air Canada are Cramping My Style

TMI: My Inner Monologue of Packing For Las Vegas

How to Pack For Your Holiday Away

Confessions of a Relapsed Light Packer

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