Travel Style: Comfy & Chic

Travel Style: Comfy & Chic

I may or may not have worn this on our flight to St. Kitts and on our return flight…ok, I definitely did. It was just soooo comfortable, and I felt chic, too. Sometimes that’s tough to pull off in a travel outfit.

Greater Than Rubies

Greater Than Rubies

Along the way, I saw a lot of ladies that looked a little miserable with their outfit choice:

  • Sky high stilettos (not at all dangerous while running to catch a flight);
  • Jeans literally cutting into their sides they were so tight (ok maybe not literally, but they had to be at least cutting off circulation);
  • Crazy amounts of jewelry that took 15 minutes to get off in the security line (everyone loved them).
  • There was also the poor woman that opted for pj’s and her luggage got lost. Oops.

It made me sad. I wanted to hug them and give them all my tips, but I refrained. No one wants unsolicited advice from a crazy lady. So, my captive audience, I’ll impart my wisdom from a few hard-learned lessons. :) Here are a few of my favorite travel outfits:

  • (Today’s look!) A super soft shirt, maxi skirt, and lightweight sweater. The hat hides the hair that looks so gross after a flight. (Does anyone else’s do that? I just feel dirty after flying. Must.shower.NOW!)
  • A maxi dress and completer piece. A lot of ladies were wearing jean jackets over theirs- adorable!
  • A tank, palazzo pants (those wide leg, super soft ones that would look like pj’s save for a good pattern), and a completer piece. I love cardigans on planes because they’re cozy for napping.

Add simple jewelry and comfortable shoes, like a cushioned sandal or flat for a final touch. (Bring socks if you wear sandals to keep those toes warm!)

If you’re flying for business and have to go into a meeting right after you land, try a jersey wrap dress (no wrinkles!) with a completer piece and a pretty pair of flats.

What are your tips for choosing a travel outfit?

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  • Meghan June 25, 2014 at 7:14 AM

    I would definitely wear this on a plane! It looks so comfortable!

    • Meghan June 25, 2014 at 7:15 AM

      I just realized how “green eggs and ham” that sentence sounded.

      • Caitlin Author June 25, 2014 at 7:31 AM


  • Amy G June 25, 2014 at 7:54 AM

    Ugh, what is it about traveling that makes hair look so bad? Sadly, this isn’t just a plane problem – I’ve had this problem many times on road trips too. Somehow sitting in the car for 8 hours can make my hair dirty. Weird.
    For my two plane trips last year, I did wear jeans, but I made sure they were stretchy, comfy ones. Wearing my jeans also meant that I didn’t have to fit them in my carry-on, which was great since jeans are a little bulky for packing. I also wore the athletic shoes I was bringing for the light hiking we’d be doing so I wouldn’t have to fit those in my bag either. Not as cute as your outfit, but still comfy enough and better than pjs!

    • Caitlin Author June 26, 2014 at 7:35 PM

      It is strange! Ah well, the travel is worth it :)

      That’s a great option, and smart thinking, Amy! The same goes for winter, when you’re packing boots and a coat. Wearing those things that are bulkier is always wise. Great point!

  • Joy June 25, 2014 at 1:50 PM

    Maxis are my go-to when traveling too! Only thing is, at one airport, I got a pat-down supposedly because I was wearing one. Not so cool. But I still usually wear them on planes — sooo comfy but chic too.

    • Caitlin Author June 26, 2014 at 7:42 PM

      Oh no! Definitely not a fun benefit of travel. :/

  • Alex @ Undergraduate Style June 28, 2014 at 11:26 PM

    Love this! I’m flying for the first time in 6 years this summer so I will definitely use these tips soon! :)

    • Caitlin Author June 30, 2014 at 9:37 PM

      Oh my goodness! How fun! Where are you going?

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