Planes, Trains and Automobiles: A Pin-up’s Guide to Travelling in Style

Travel Elvgren

Ahhh… The infamous travel bug. Once it sinks its teeth into you, it’s hard to get it out of your system. However, in hearing over the holidays that a new ultra-low discount airline, NewLeaf Travel, will begin flying soon from select cities in Canada, I admit I have mixed emotions about the news. I understand the need for affordable airline services in today’s economy—and maybe I’ve been watching too much Pan Am lately—but I find myself quite saddened to see the once-glamourous experience of air travel further reduced to nothing more than a secured seat and seatbelt from Point A to Point B. Add to that a world of heightened security and regulations, and the business of travel is now nowhere near the fun experience it used to be.

Since entering the vintage scene three years ago, I have tried to sneak touches of yesteryear into my daily life, including my travels. I can certainly say that I’ve had my fair share of foibles and moments of sheer awesomeness in the process. 😛 From those experiences, I want to give you the top five lessons I’ve gleaned for setting off into the sun in style without being “burned”:

1)      Remember that less is definitely more.

Shortly after I started adopting the vintage look, I went on a road trip to the United States. Of course, I wanted to look as fabulous as I felt, so I went all out: Headscarf, cat eyes and everything. When my companion and I got to the U.S. border, we handed our passports to the officer, and answered the standard questions. All good so far. He looked at my companion and his passport, and then looked at me… and kept looking. Back and forth he went from my passport to my face, and I started to get nervous. Finally he let us go through, and I learned my first lesson in travelling ala vintage: Try not to deviate from your passport too much.

I don’t blame the officer at all. I mean, here is a photo of what I looked like per my passport at the time, and what I looked like that day. Yeah… I would’ve had my doubts too. 😛 They say fashion and beauty have their prices, but sometimes, they’re just not worth it. Do yourself a favour, and save the winged eyeliner for when you arrive at your destination.

2)      “Hairy” hold-ups can be avoidable.

We’ve all seen it at the airport, and we’ve been guilty of it ourselves. You know what I’m talking about – wild, unkempt hair that looks like your last connection was on a broomstick. Logically speaking then, why would you NOT want to set your look with perfect rolls and curls, and stand out in a sea of frazzled frumpiness? Two words: Metal detectors. Most pin-up styles that look great in photos require bobby pins, and those handy little helpers may cost you an extra scan and pat-down if you beep going through.

You could sleep in rollers before your flight and go for a nice Marilyn set without the extra hardware, but who wants to add yet another task to the already too-long pre-travel checklist? The solution? Wear a fabulous hat. I’ve done this on two trips to the U.S. now, and it has worked magically. All you have to do is quickly take it off and put it in the basket with your other belongings, and voila! You breeze through that nerve-wracking walkway of plastic and wires, and put it back on once you’re through. You’ve got one less thing about your look to worry about, and everyone will stop and take notice for a GOOD reason. 😉

New pin-up

That being said, just be sure to take off your hat once you reach your gate and are boarding your flight. The airline staff needs to see you without it while they check your passport and boarding pass, so just take it off while you are in line, and quickly put it back on after you’re clear to board.

3)      Protecting your feet doesn’t have to leave you feeling flat.

Yes, those gorgeous Mary Janes would look awesome while strolling from gate to gate, but yet again, what will happen when you reach Security? We all know how frustrating it is when someone ahead of us is struggling to untie crazy straps and laces while taking their shoes off. Do you really want to do that to everyone behind you? Plus, even without straps, those heels will leave you grouchy and miserable by the time you reach your destination. Who wants to start a holiday as Flightzilla? Ballet flats are the perfect solution for breezing through Security quickly and easily, and adding a supportive insole will help make sure your feet aren’t killing you when you arrive.


If you’re worried about walking barefoot on those nasty airport floors, no problem! Just put on some cheap nylon socks before you leave for the airport. I know it might not look the most fashionable, but once you get through Security, you can quickly take them off as you put on your flats, throw them in the nearest garbage, and clean your hands with some hand sanitizer. On both flights to the U.S., no one said anything when I did this, and it certainly made the process a whole lot easier for everyone. If you have multiple stops on your journey and know that you may have to go through Security again, just keep as many extra pairs in your carry-on as you may need.

4)      Fashion and function are sisters that can actually get along.

Until we can go Star Trek and beam from place to place, most modes of transportation involve some form of sitting… for long periods of time… :\ Sweat pants and t-shirts might be the most comfortable, but c’mon. How glamourous is that? On the other side, sitting in a tight wiggle dress that could double as a corset isn’t ideal either. And remember what I said about metal detectors? That goes for your underwear too. Good quality garter belts are made with metal clips, and there is no sense causing a commotion at Security because of those dainties. 😉

Paper Doll Leopard Dress

Comfort is in the fit of the wearer, so if you have a vintage outfit that you find is comfortable to sit in for long periods, go with that one. For my go-to travel outfits, I prefer either wrap dresses, or ones that are made with breathable, stretchy materials. Paper Doll Productions makes some awesome dresses like that. They can be easily cleaned, and certainly don’t look like what most everyone else is wearing. I’ve gotten many compliments dressed that way, and find layovers, long flights and bus rides so much more enjoyable in them. In addition, they even make a great cover-up over your bathing suit when you’re not swimming.

5)      The right carry-on doesn’t have to de-rail your sense of style.

We all know that fanny packs are the ultimate of travel fashion evils, but they’re so handy!!!! Is there any other way to carry all the passports, regulation-size toiletries, and other things we may need and still look awesome? Actually yes! A former staple of every woman’s luggage, train cases are perfect-sized carry-ons that you can use as a purse on trips, and stow safely below seats on flights. They contain many pockets to organize your things, and room to hold all your travel necessities in mandatory baggies.


I love the ones from Fluff in particular, but there are other designers that make train cases as well. As with anything, be sure to double check the carry-on regulations for the specific airline, bus service or train service you will be using. Everyone does things a little differently, and there is no point using a fabulous bag that will lead to a not-so-fabulous extra fee!

But hey! We’re just scratching the surface here. I want to know what great tips and tricks you have found to keep yourself looking fabulous on your own adventures. Please feel free to share your comments below, or on the Canuck Pin-up Facebook page.

Bon voyage, my friends, and may you find happy trails as you embark into 2016!

Kitty 011

Always with love,


The Canuck Pin-up


2 thoughts on “Planes, Trains and Automobiles: A Pin-up’s Guide to Travelling in Style

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