Comfy, Funky Walking Shoes for Travel

When you travel, comfy shoes are a must. Sporty sneakers or walking shoes fit the bill, but they’re 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, funky or even tomboyish?

Here’s a look at some funky walking shoes for travel that are creative, playful and easy on your feet.

fly london shoes


shop the look small

Black Fly Yala Sandal  / Jade Wedge Leather Sandal / Tan Yuke Platform Wedge

Fly London  – For Funky Types

If you like to stand out in a crowd, then these shoes are for you. Fly London makes funky, comfortable shoes that are youthful and fashion-forward. 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 looking, but they provide great support for your feet. They’re one of the most loved funky walking shoes for women and have a huge following, especially among creative types.



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Oxford Sneakers- For Tomboy Style

Another option for a travel shoe that is a little more whimsical is a soft suede Oxford shoe. This one on the left is  the Munro Wellesley Oxford Sneaker.

Leave it to Munro 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.

Another classy casual walking shoe is the Sanuk Bianca Oxford Flat.  It’s soft, unconstructed, elegant and looks as comfy as a slipper.

Can you wear Oxfords with dresses or shorts? Check out my post on How to wear Oxfords and see what a versatile shoe the Oxford is. 

Join the Conversation

24 thoughts on “Comfy, Funky Walking Shoes for Travel

  1. What are some alternatives to the Fly wedges shown for those who have been told not to wear ankle straps to draw attention to thicker ankles? I don’t love flats of any kind, unless it was sandals weather.

  2. I’m searching for the right shoes to wear/take to Europe this spring and summer. I’m 70, 5’1″ and my ankles and feet swell. I want comfort with funky classic style. Have been steamed away from sneakers, particularly any that post USA on the back. I’ve worn Dansko Sophie’s and classic Dansko for years. Like Dansko Sabrina but have read their non slip tread is slick. Help.

      1. Thank you for your response.
        Shoes with hig ankle straps do not work for feet and ankles that swell.
        All of the other straps allow swollen feet to protrude. Not pretty.
        Thanks anyway.

  3. 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.

    1. 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. 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

    1. 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. 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.

  7. 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.

  8. 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)

  9. 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.

  10. 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.

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


    1. 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.

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