In Plane Sight: How I Dress for Traveling

Though I still have a few more sets of pictures that my sister-in-law took (that are much better than these), I just flew back to Illinois on Saturday and I wanted to share a little about how I dress for traveling. Since I'm a plane every few months going back and forth between California and Illinois, flying has become second nature for me. However, even sitting in the airport for two hours, on a plane for four hours, and in a car for three hours (a typical day traveling to where I live in Illinois) can't force me into sweats. Here are my rules for dressing comfortably for travel, without sacrificing style:

1. A comfortable dress with a defined waist — Everyone has things that they're most comfortable in and dresses are mine. I feel much less restricted and more relaxed sitting in a dress on a plane than in anything else. I always make sure to choose one that moves easily, but has a defined waist so that I don't have to worry about taking off a belt when going through security. This white Francesca's Collections one is perfect because it's lightweight and has a tiny, hidden bit of elastic around the waist. 

2. Heavy shoes — This one is always a little tricky because I like to wear heavy shoes so that way I don't have to pack them, but I also want to be comfortable. This rules out any heels that I might pack (which usually isn't very many), but also my most comfortable pair of flats. I usually stick to a boot that's easy to take on and off. I always overpack, so making the weight limit with my suitcases is a constant struggle. Wearing my boots on the plane allows me to eliminate some extra weight in my luggage.

3. Some sort of layer — Like the shoes, this serves two purposes. I like to wear something a little heavier so that way I don't have to pack it, but it's also because it gets cold on the plane. I just got this denim jacket last week and I'm a little obsessed. I've been wearing it with everything lately, and it was just the right kind of layer for the plane.

4. Glasses — I usually wear contacts, but since I take such early flights, I try to sleep a little on them. This also eliminates any worry of contacts drying out or anything of that nature.

5. Skip the accessories — It's always a little strange for me not to be wearing any rings, but it's not worth the hassle of taking them off for security and potentially losing them. It's possible to stay stylish when traveling, but keeping it simple is best.

I hope this might help some of you next time you're traveling somewhere. While I took these pictures last week, this is exactly what I wore on Saturday and I can happily say that it lived up to the test. I apologize that these pictures are so bad and that some are out of focus. Everything I did last week was done in a hurry, and stocking up on pictures was no exception.

Dress: Francesca's Collections
Jacket: H&M
Boots: Modcloth


  1. I love this outfit, for traveling or not! I dress similarly when I travel. People always think I'm crazy for wearing a dress to the airport, but if I've got on a cute knit dress, I couldn't be comfier sitting for hours!

    Ladyface Blog

    P.S. Loving your post title!

  2. This is the perfect travelling outfit, I love the polka dot dress with your denim jacket! And you look so adorable in your glasses!! It's so important to be comfortable on flights for sure, scarves, extra sweaters just in case are always necessary. The worst part is the airport is always so warm and the flight is always so chilly, ugh. I had problems at security because of a "studded" (it was soft rubber) bracelet, so yeah, no accessories is wise

  3. That is definitely the perfect plane riding outfit! Love it. (Also, you look super cute in glasses and I want that jacket!)

    Dresses make a lot of sense to travel in since you can move more in them.

    Sadly, I feel like I now take forever going through security with getting my meds through. I'm not sure why this is. No security ever gives me a hard time about it (There is an exception to liquids if hey are medical, but I wasn't sure how the TSA would handle that), but it just seems to add to all the things you have to put through to be X-rayed. - Truth is though, I'm probably just slow and travel with a guy with a lot of technology in his bags, lol.

    Glad you made it back safely!

  4. So so cute!! Perfect traveling outfit! I'm going to remember the boots thing. I tend to wear sneakers, but then it takes forever to put them back on. Okay, not forever, but I hate tying my sneakers when everyone is waiting for me to hurry up. Boots are a great idea!
    Sincerely, Sara

  5. Nice set of tips! I personally would swap the dresses for jeans, but that's just because I like hiking up my feet during plane trips. You hit the nail on the head for wearing the heaviest clothing though - such a smart idea!

  6. You are so adorable! Love that gorgeous smile. I also love your look - simple pieces but you look totally put together (and comfy). I love a good short boot with a girly dress too. ;)

    Merch Maven

  7. I love this outfit and it's basically what I wear too. Only I wear a scarf for a blanket/pillow. Also these boots are amazing.

  8. I love your outfit here, especially that dress. It all looks really adorable together!

  9. Love this outfit, you look wonderful!!

    <3 Megan

  10. Elana, you look so cute! This is a great traveling outfit. And I love the glasses on you!

    xox Sammi

  11. These are great tips for traveling fashionably Elana! I love what you wore for your flight, its perfect. Simple yet cute and functional. Good tip with the heavy shoes.

    The Dragonfruit Diaries

  12. I agree with the glasses. There's nothing worse than having your contacts dry up in the airplane (no matter how short your flight may be) and having to go inside the very unsanitary, shaky lavatory to pop them out into your lens case. I love this outfit! When I travel, I like to wear my knit maxi dress. It's soft and stretchy, and since it's long, I can curl up in all sorts of weird positions when I take a nap and drape it over my feet to keep me warm when no blanket is available.

  13. Great tips for traveling. For some reason, I always want to be in jeans on a plane - I'm always cold, and the more between me and that airplane seat, the better! ;o)

  14. I love how comfy and laid back this outfit is!Please check out my fashion blog at I would love to follow each other!

  15. Great post girlfriend- wait you mean you don't wear sweats and uggs to travel in?!?!?! Haha one of my favorite past-times when I'm traveling (yup, multiple times a year, CA --> Nashville, takes all day) is making fun of people wearing gross travel outfits. Like, seriously?

    I also try to wear heavy things so I don't have to pack them! Booties (summer) or full boots (winter) pretty much always make the cut. And I like to have socks/a sweater because it does get hot on planes! I don't normally wear a dress...and yet, that does seem really comfy. Maybe I'll try that out next time!

    perfectly priya

  16. Your booties and denim jacket are super cute!

    Xo, Hannah

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