Comfy Travel Shoes With Whimsical Style

When it comes to traveling, comfy shoes are a must. Sporty sneakers or walking shoes fit the bill, but are usually more practical than stylish.

A pair of cute ballet flats or sandals can also work and will help you avoid the tourist look, but what if your style is more whimsical?

Here’s a look at some shoes that are creative, playful and  comfy.


Fly London

If you like to stand out as an individual then these shoes are for you. Fly London shoes are fashion forward, youthful and have lots of personality. The company is known for using traditional construction techniques in unexpected ways, and for not linking their shoes to any particular season or trend.

Not only are Fly London shoes distinct, they are comfy too which makes them a favorite shoes with travelers looking for a shoe that will let them travel the world in style.

Shop Fly London Shoes

TRAVEL OXFORD – It’s a winner!suede oxford

Another option for a travel shoe that is a little more whimsical is this soft suede Oxford shoe. This is the Zero Grand perforated Oxford.

Leave it to Cole Haan to come up with a breezy boy meets girls shoe like this that is flexible, lightweight and cushioned. More dressy than a sneaker, but less formal that an Oxford this is a great option for travel.

And don’ think you can’t wear this with dresses or shorts. Check out my post on How to wear Oxfords and see what a versatile shoe this is. Great neutral color too.

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  1. Hi Deb
    I love oxfords, but they need to have a feminine touch. I have a pair of Brown Born that I will wear in the fall. I think more companies are making comfortable shoes stylish, and these are an example!


  2. Hi,
    I love the oxford shoes in the attached picture from your article “Comfy travel shoes…”. Do you have any details on where to get these shoes?
    Thank you,

  3. OK, I took the traveling advice to mean once you get to your destination, oxfords can be a great alternative to sneakers or ballet flats for walking and sightseeing. Not necessarily wearing them for the actual flight.

    There are some comfortable and fun looking oxfords that I’ve worn for a whole day of shopping. I wear them with little ped socks and find them more secure on my feet for walking quickly on sidewalks. It’s not much fun having my feet slip out of my ballet flats on the sidewalk as I’m trying to keep up with the pedestrian traffic! And they’re just a lot nicer looking than sneakers, at least for me.

    I love oxfords! They’re one of my favorite types of shoes and I’ve got several pairs. Thank you for the tips on the clothing to pair them with.

    • Hi Olive,
      I’ve been in airports a lot this summer and I have seen several women wearing oxfords with skinny jeans. It all depends on the shoe. Some oxfords softer and comfier than others, and of course they are flat, so they are good for those long walks to the flight gate or customs desk. I imagine they’re not as easy to take off at security like a slip on would be, but really, it’s not big deal if you want a bit of style. Thanks for popping in to comment. Cheers! Deborah

  4. Pamela Jo says:

    I have loved loafers for a long time and am so happy to see them mainstream again. My question is about socks. My kids do not wear socks with their loafers in this trend, but I always have worn them…even in summer under pants I have on an anklet in an appropriate color. I only wear my loafers with pants. Are socks okay or frumpy? Otherwise I get rubs or perspiring feet at times. What do you advise?

    Pamela Jo

    • Oh great point! Yes, the trend is to go sock less with loafers because socks will ruin the look. You can try wearing the little peds with them or if you are wearing long pants you can certainly wear socks if you are wearing the tie up loafer, but the ones you slip on should not be worn with them.

  5. I see very little appeal in flats, period, let alone lace-ups. I sure wouldn’t wear them on a plane. Most airline screening stations do not even have a chair for you to sit down in to put your shoes back on and I would rather not have my behind sticking up in the air in front of all the other passengers. I travel in comfortable slip-ons with a slight (sturdy) heel or, when the climate permits, my Naot sandals. I rarely do short hauls, and my feet and legs swell on long flights to Asia, so the sandals are a better choice for me. I also carry a pair of those disposable slippers that they give you in hotel rooms and wear those on the plane, because it can be a pain to try to get back into my shoes to go to the washroom while on the plane. And washrooms can get pretty scuzzy by the end of flight. I just leave the disposable slippers on the plane as trash.

    For a 13 hour flight, I go for comfort over fashion, although I generally do wear something that I can wear again while on the trip. I also pack a pair of pj’s and change into them once the meal has been served and everyone is ready to go to sleep. I change back into my street clothes an hour or so before landing and come off the plane looking neat and refreshed.

    On flights within North America, what I wear depends on what I have to do when I get off the plane. If I am going straight to a meeting, I wear business dress; if it is a vacation, then I dress for the weather on the other end.

  6. Hi gals, what can I wear with a wedge Mary Jane?

  7. I definitely NEED some whimsy in my wardrobe! I need to find some cool shoes! Great post!

  8. Celeste D says:

    I like the leopard print shoes.

  9. Flats don’t work for me–no support for walking distances through airports and city blocks. My comfortable walking shoes have buckles and I wear them through TSA with my carry-on, my purse, my laptop case & jacket. I tell the antsy pants in line behind me to go around me. I’d rather spend 1 minute or less juggling stuff and looking sharp, than be achy and whiney for hours.

  10. kimberlea says:

    Check out the Munro shoe brand, I have five different styles and absolutely love them! I also need arch support and I wear a 10 1/2 WW in their shoes. All five of the styles I was able to put on, perfect fit first time, and best of all……. was able to wear them all day shopping. True test of a great fitting shoe, no blisters or sores!! Nordstroms carries them and are great with their free shipping and free return all the time.

  11. Mamavalveeta03 says:

    I agree with @SusieQ, wholeheartedly! No way would I wear lace-ups, buckles or anything complicated and time-consuming to the airport. As a savvy air traveler, it’s ballet flats for me. (also, my feet can swell, so nothing confining)

  12. What about penny loafers? They are a classic that is always in style. My mom has an amazing wine colored pair that she has worn for years, and gets many compliments on them. She’s 77 now, and doesn’t look a day over 60. I wish I had a pair just like them.

  13. Great post – I am loving the leopard print shoes!

  14. Lace-up oxfords while traveling? At the airport when I have to take my shoes off? And then get them back on before someone steals my stuff in front of me while trying to stay out of the way of the person behind me? No thanks. Slip-ons for me.

  15. Hello Deb,
    LOVE, LOVE, LOVE your website! Do you have suggestions for stylish shoes that have arch support and a wide toe box?


    • I also suggest Munro as well as Ziera shoes, Both have some style and are avail in wide width which is unusual for comfortable shoe brands. . FYI I also just discovered that Taos makes 2 styles of their comfort shoes in W width.