Travel Outfits That Are Both Comfy and Cute? Easy!

Vacations are wonderful things, but the actual travel part can be a total pain if you’re not wearing the right clothing.
Publish date:
August 12, 2014
shoppables, travel, holiday, sweatpants, Seamly, plane rides, travel outfits, comfy clothing

Every single time my mom gets on a plane, she wears super high stilettos and tight pants. Racked with anxiety and fear of flying, she always seems to be so uncomfortable on the plane that it actually hurts just to watch her. Though I know her fear has a lot to do with the pained look on her face, I can’t help but imagine a more comfortable outfit would make the whole experience a lot less horrible.

As for me, I love going on trips, I love airports, and I even love flights and flying, but I can still admit that being stuck on a plane in the wrong outfit can be day ruining, and really, who wants to ruin a day of their vacation over clothing?

So what’s the key to dressing for travel? Layering is paramount, considering you’ll most likely be headed somewhere with a different temperature than the place you’re coming from, and you’ll be dealing with insane plane air conditioning (a part of flying I deeply loathe) en route. There’s also definitely a need for a bit of planning based on where you’re headed and what your plans are when you arrive; you don’t want to end up half-naked on the streets of Dubai trying to catch a taxi, or in a sweater and cargo pants if you’re going straight to a business meeting in the Bahamas. Most importantly, whether you’re driving, flying, boating, or any other “ing” to your destination, comfort is key!

Here are some of my go-to travel outfits and essentials. Just think of me as your wardrobe travel agent!

If I'm heading somewhere with the same temperature as where I am (or colder), I always overdress. I have never ever been on a plane that was warm, ever, so layering for flights is key if I don't want to waste all of my trip energy shivering before I even arrive at my destination. Super soft fitted sweatpants are one of my travel essentials because they're warm, flexible, don't wrinkle, and they're easy to strip off and trade for shorts if it's warmer than expected when you land.

They also double as pyjamas while you're away, so they're not totally useless post-flight. An oversized loose t-shirt is also a great travel item, though I don't suggest white if you can help it (no one wants to look sloppy and covered in stains!) Finally, shoes: loafers are by far the best plane shoes ever. They look great with socks, they're easy to slip in and out of (I'm a sock-only sleeper on planes), and they're so comfortable!

When heading somewhere warmer, I always try to plan ahead as best as I can while still taking plane coldness into consideration. Loose shorts and a soft T-shirt are a great place to start, but if you board wearing just that, chances are you'll end up buying some horrid plane blanket just to survive the trip. I highly suggest donning a small warm hat or headband that you can tuck away into your bag upon arrival for added coziness, and I always wear my biggest pair of shoes on the plane, which in this case means little ankle boots.

Most importantly, bring a loose open sweater! These kinds of pieces are practically made for flying, plus they fold up small, and can come in really handy if your tropical vacation involves a few surprisingly chilly nights. I'm currently loving this sleeveless style from Seamly, an ethical American-made company with awesome basics.

Accessory wise, I find a big scarf is crucial for all flights any time of year because it can double as a blanket while in the air. Hats are also great for keeping warm, and thick socks are a must if you're not wearing a closed boot or shoe. Finally, opt for a big tote as your "purse"- you'll be able to fit a ton of stuff in it without going over your carry-on allowance, and you can even stow a smaller purse inside for when you get off of the plane and want to look a bit more put together. Oh and sunglasses, because fancy.

Attention all passengers: we've included in-flight shopping on this trip to ensure travel comfort for all!

What do you wear for your travel adventures?