How to Look Good in the Airport: A Guide on What to Wear When Traveling

Traveling is full of excitement; however, some of the most exciting bits happen before the exploring actually takes place. Planning a trip is half the fun – the excitement builds for your new adventure, you think of everything you’re hoping to do, daydreaming about the new city you’d be in right now if only you weren’t stuck in the office and the trip still wasn’t 100 days away. The anticipation leading up to your travels can keep you going even when your trip starts to get a little too…adventure-y (read: getting lost, losing luggage). Packing, although the epitome of death for some, is no different. There’s anticipation on what you’re going to wear on those nights out across the world; the books you’ll read on the plane; the playlist you may have made specifically for your destination; and the chic outfits you’ll be wearing on your day-to-day excursions.

Keeping yourself looking fresh and stylish, while also simultaneously being comfortable, can be a tricky packing dilemma. But, once you’ve figured out your go-to outfits, you won’t have to tear your closet apart for hours trying to figure out if sky-high heels and yoga pants really look that stupid. The answer is always going to be yes.

There are a bunch of things I refuse to wear while traveling (anything over day-trips) and I’ve put together a few go-to outfits whenever I board a plane.

Comfortable Shoes that Look the Part.
Believe me, we’re not talking about Reebok sneakers or old lady orthopedics, although you may think the latter in two seconds, because…loafers. The fact that people have not started wearing loafers with every kind of outfit is mystifying. Flats tend to pinch and offer way less support than a beautifully crafted loafer, so I shy away from standard flats and hit up my comfy walking shoes of choice: loafers.
Why?
They look good with, nearly, every type of outfit whether it’s tights and a cute dress, leggings, jeans, or low-key jogger pants. Just by adding a comfortable pair of Tod’s or embellished Michael Kors, you can make leggings look 100x more elegant. At least, as elegant as leggings can look.
Loafers are perfect for running across airports when that perfectly crafted connecting flight schedule gets messed up; they’re easy to slip on and off when rolling through security; and they double as chic street-wear during tours in whatever city you’re in.
A close runner up to my all-time favourite shoe? Keds. (or converse)
They may not dress up leggings, but you can tone down a dress or skirt with them, and they keep you comfortable. The one drawback? Laces.
Ain’t nobody got time for laces in the airport.

Loose, but Stylish, Pants.
Dresses can be an easy fix for pretty much any type of fashion conundrum (Clubbing? Dress. Drinks at the pub? Low-key dress. Work? Dress with blazer. Exploring a new city? Dress and converse.), but if you’re prone to sitting in weird positions and don’t want to wear leggings, then it’s best to pack those dresses in your suitcase and take out your best pants.

Jeans, unless you’re stick thin and are wearing the boyfriend variety, are not comfortable to sit in for hours upon hours. Slim, cigarette trousers, although fashionably elegant, feel the same as jeans with slightly less breathe-ability.

A good jogger pant is perfect for long-haul flights and nights spent in airport terminals. They’re comfortable, cool, and stylish. You can dress them up with a pair of heels (kept in your carry-on, of course) to meet a significant other right from baggage claim, keep them casual with a pair of loafers, or dress them down with a pair of Keds or Converse.

Soft and Flowy T-Shirt.
Nothing feels worse than sitting in your seat after 8 hours of traveling and starting to feel too tight and uncomfortable. The culprit? That super cute top you put on earlier that morning that looks amazing with your outfit. It’s now starting to feel life-threatening constricting, the buttons feel like they’re about to explode, and you just want to rip it off and lay down on a couch or a bed.

Unfortunately, none of those options will be possible for at least another few hours. Keeping your outfit put together with a well-made, soft, cotton blend (bamboo or organic will make the softest) t-shirt will also keep you comfortable and keep you from having a breakdown mid-flight. Keep it loose and flowy, tucking in the front to bring your figure back and take you away from muumuu status.

Layers.
Are you leaving -50 to head to warmer weather? Running from the car in your spring – or summer! – clothing in the dead of winter is something we have all done as Winnipeggers, but it’s always something you swear you’ll never repeat. If your climate is slightly chillier (or much chillier) than the climate you’re heading to, layer up. It’s easy to shed layers than it is to have sweaters, jackets, or blankets appear from thin air, unless you’re Harry Potter.

Layers are perfect if you’re going from one extreme climate to the next. They’re also perfect for freezing cold airports, stifling train stations, and chilly, then hot, then chilly window seats.

Add a scarf, a sweater, and/or a light-weight jacket. Once you’ve boarded and are feeling a bit warm, shed the layers and use as extra make-shift blankets or pillows. You’ll look stylishly put-together right until the end.

Practical Jewelry.
So, your outfit is looking beyond adorable and you’re ready to run outside to the cab waiting patiently, but there’s something missing. The thought of losing precious gems on their travels scares a lot of people, and that’s understandable. Me? I want to live, and look, how I do back home – only better. So, the jewelry I wear at home is always coming with me. That means pearls in the ears and a watch on my wrist. The two pieces are simple, keeping clunky and heavy jewelry away from body-scanners (let me tell you about a time in Vegas where a super cute necklace of mine had them searching through my bag, determined to find a knife) and keeping you from getting neck pain after wearing that necklace bib for hours upon hours.

Keep it simple, keep it practical, and you’ll look effortlessly cool.