In Organization, Packing, Style, Travel

Perfect Travel Outfit — Comfortable and Easy

Traveling has given me a healthy appreciation for being comfortable, simple and chic at the same time.

I always cringe when I see girls in their leggings, a shirt that barely covers their bum or stomach, and/or wearing these awful boots with 50 straps that they take forever to remove at the security checkpoints.

Even wearing heels at the airport is not a good idea.

When I go straight to the airport from a client’s site, I take the time to at least change my trousers and my footwear, but I never try to wear heels when I’m at the airport, lugging my carryon and (perhaps) having to sprint for the gate.

Men aren’t so much better in terms of being able to be comfortable and organized either, with their laced boots and not understanding that “EMPTY YOUR POCKETS” is not an idle request made on a whim.

Here’s my go-to travel outfit:


Comfort is key. I don’t like wearing anything too tight, too loose, or too short.

I also want to look somewhat chic, because you’d be surprised how many people I run into at the airport when I least expect to see them.

Besides, looking nice should always be a bare minimum requirement before you leave your home!!

 Other Tips for Traveling:

  • If I wear jewellery, I always remove it & store it while I am in line for the security check
  • I wear layers, so I can remove one when it gets too warm or add one if it gets cold
  • I always put my liquids in the sealed bag before I get to the airport
  • …and the liquids in the sealed bag are in an easy to reach pocket, or in my purse
  • My laptop is also in my purse, not packed away (iPad doesn’t need to be removed)
  • I try not to wear my winter coat — I pack it away instead & rely on the cashmere wrap
  • I never check in any bags unless I absolutely have to; carry-ons only!

If you want some celebrity inspiration, WhoWhatWear had a few travel outfits featured.

I picked out my favourite:


Via WhoWhatWear (go there for more pictures)

Ashley Olsen’s look is the closest to my ‘ideal’ traveling outfit. Flat shoes, a warm comfortable coat, and a big enough bag to hold your in-flight entertainment.

One thing I will point out is that they all seem to have sunglasses on. This is to hide their tired, red eyes that everyone gets when they travel.

 What do you wear when you travel?

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Sherry of Save. Spend. Splurge.

Am my own Sugar Daddy. Am a millionaire at 36 after getting out of $60K of student debt in 18 months, a little over a decade earlier, using I have worked 50% of my career (taking 1-2 year breaks), and quadrupled my income within 2 years of graduating, going from $65K to $260K with an average lifetime savings rate of 50%. I have 11 side incomes that are on track in 2020 to make me $50K - $75K. I could retire today if I wanted, but love my work-life balance as a freelancing consultant in STEM (Science, Technology, Engineering, Math). I am all about balance - between time and money, and also enjoying my money. I also post daily on Instagram @saverspender.

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  1. Tania

    Nothing wrong with leggings if paired with a long enough swingy top. I wear an oversized nation t (they always have interesting cuts), cropped leggings, silver ballet flats ( they do look good on non-ballerinas!) and a cardi coat. I carry an uggs in my carryon to wear on the plane.

    1. saverspender @ save. spend. splurge.

      The leggings I am thinking of are sheer, stretched out too far (too small) and show every jiggly bump with a short top. I have seen too much of this on escalators and stairs. Guys think it is the next best thing since sliced bread but it just looks vulgar to me. I would agree that having a long top to cover everything would be more appropriate.

  2. Do or Debt

    I always wear jeans, slip on shoes and an easy to remove jacket. Laptop is out and ready, liquids in a bag. I only do carry on as I had a bad experience with checking bags, so I travel light and efficiently! I love your travel outfit!

  3. http://michellesfinancejournal

    I fly maybe once a year, so it’s not something I think about a lot. I’m one of those girls who wears leggings at the airport. If I could wear it all the time, I would~^^
    I wear a short comfortable skirt over it and a t-shirt. I get cold all the time, so I have to have a cardigan and a big scarf or a wrap. Sometimes, I bring a thin baby blanket. I know I’m not a baby, but I love them~

  4. sense

    Haha, I look like a complete hobo when traveling. The problem is that I don’t sleep on planes and I look totally awful/am incoherent after traveling for 24+ hours anyway, so why try? I’d rather be comfy. Big hoodie sweatshirt, stretchy yoga pants, fluffy socks (I take my shoes off on the plane IMMEDIATELY. I also carry a change of clothes and my toiletries so I can pretend to ‘go to bed’ and ‘wake up.’ Even if I don’t sleep, it’s amazing how much more amazing I feel when I wash my face and go through my normal evening and AM routines.

    I have my whole plane traveling schtick and accouterments DOWN! I can’t wait to have enough airpoints to fly business class. Maybe then I’ll try to look nice as I have a chance of sleeping! 🙂

  5. Jane Savers

    I don’t travel and I don’t have a wardrobe but I am interested in building a wardrobe and I guess that the colours in your sample travel outfit (navy, white and beige) would be a good place to start.
    I do not like ballet flats except on ballerinas and those Olsen twins usually look like they borrowed their clothing from someone a size or two larger.


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