Comfy Travel Shoes With a Touch Of Whimsy

When you are travelling you want something comfy to wear on your feet. But what happens when you want something more than that? Here’s a look at some shoes with whimsy.

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  1. 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.

  2. 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.

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

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

  5. Celeste D says:

    I like the leopard print shoes.

  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. 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.

  8. 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)

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

  11. 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.

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