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Ask CF: What Are Some Comfy Outfit Options for Touring on Vacation?


Fashion while touring in Seville, Spain
This is me in Plaza de España in Seville, Spain. This was my favorite outfit I wore while touring because it was so comfy and I loved the way it looked!

Welcome to the latest edition of Ask CF! Every couple of weeks, we select a reader fashion question and answer it here on the site. Do you have a specific fashion question for us? Scroll to the bottom of this post to learn how to send it our way!

Ask CF Question

Dear CF,

I always have trouble finding comfortable fashionable shoes and outfits for walking around on vacation. I’m going to Europe this summer and I know I will be walking around a lot. There will even be the infamously uncomfortable cobbled streets! If you could point me towards some outfits and shoes that would work well for long days walking around that would be a great help! Thanks!


Our Response

Dear Eurotrip,

How exciting that you are going to Europe! I just got back from six months studying abroad in Europe and I had an absolute blast! I hope you enjoy your trip as well, as I’m sure you will.

As someone who has experienced those infamous cobbled streets on a daily basis and who spent many weekends touring around countless cathedrals, national monuments, and museums, let me be the first to tell you that you have the right idea about bringing some comfy clothes — especially shoes! — on your trip.

Additionally, since you will surely be taking tons of pictures on your adventure, you will want to find the perfect combination of style and comfort for your trip. I have created a few outfit options below to help you do that. I hope you find them useful. And lastly, enjoy Europe!



Outfit # 1

What to wear while traveling: Shorts, sunglasses, sandals, collared top
Product Information: Top, Shorts, Bag, Sunglasses, Sandals

This look would be perfect for a warm day touring around a city. Shorts like these pink ones above provide both comfort and functionality. Sleeveless, collared tops have been all the rage recently and this top combines the look with this season’s floral trend. Accessorize with some pink jelly sunglasses to keep your eyes protected, and add some yellow sandals. Lastly, you need a bag. From my experience, I like to bring the smallest and lightest bag possible, as carrying them around day after day can get painful if they are too heavy. This crochet fringe cross-body would be perfect.

Outfit # 2

What to wear while touring on vacation: Dress, sandals, watch, bracelet, sandals
Product Information: Sunglasses, Dress, Bag, Sandals, Watch, Bracelet

Another great outfit option for vacation is a maxi dress. Start off with this black one and accessorize to your desire. For this look, I choose some leopard print sandals, a simple watch, bracelet, and tortoiseshell sunglasses. Even though it might seem kind of touristy, this Paris bag stole my heart – just be careful not to fill it with too much stuff! And even though I don’t have it pictured here, you could easily throw on a cardigan, leather, or jean jacket for added warmth or when touring any sacred places.

Outfit # 3

What to wear while touring on vacation: Pants, sweater, sneakers, sunglasses, striped tote, polka dot earrings
Product Information: Earrings, Sweater, Sunglasses, Pants, Shoes, Bag, Watch

If you want a little more coverage, I created this unique look with pants and a sweater. Floral pants have been extremely popular lately, and I always love the idea of mixing prints. The trick to mixing these prints is the scale – since the stripes are large, they won’t compete with the floral pants. I think most people would agree that sneakers are the way to go when it comes to comfy shoes, and there’s nothing more classic than a pair of white hi-top Converse. Finish the look with some sunglasses, a striped tote, a watch, and polka-dot post earrings.

Outfit # 4

What to wear while touring on vacation: Romper, necklace, sunglasses, comfy ankle booties, cross-body bag
Product Information: Romper, Necklace, Sunglasses, Boots, Bag

A romper is a great addition to your packing list for any vacation. Similar to a dress, a romper takes care of an entire outfit with one piece making it easy to pack as well as to throw on for a day touring the city, heading to the beach, or exploring the new city’s nightlife. This bright blue belted one would work great with fun accessories like a simple pavé necklace and cool sunglasses. For functionality, add on some comfy ankle booties and a neon cross-body bag for that extra pop.

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What do you think?

Do you have any summer trips coming up soon? What do you like to wear when touring? Do you have any further tips? What has been your favorite vacation spot? Which places are you dying to visit? What would you wear there? Please let us know what you think by leaving a comment below! 

Posted on on July 15, 2012 / Filed Under: Fashion Tips / Tags: , , , , , , , , , , ,

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30 Responses to “Ask CF: What Are Some Comfy Outfit Options for Touring on Vacation?”

  1. 1
    July 15th, 2012 at 7:36 pm

    I’m dying to go to Paris, and planing to go there in the winter. Also I’m doubtful of what to wear in winter that can be both comfortable enough to walk and also fashionable. Probably flat boots or ballet flats with tights.

  2. 2
    July 15th, 2012 at 8:32 pm

    Outfit 3 is my fave! so nice! :):)

  3. 3
    July 15th, 2012 at 9:15 pm

    i’m from germany and currently studying in the uk, and since travelling in europe is quite cheap i’ve been to most of the european capitals, so let me tell u: the first two outfits just work if u are in italy or spain :) u need some warmer clothes in most of the other countries, even in france … and just to tell u flipflops or sandals get totally uncomfortable while walking on those cobbled streest!
    i would say bring some converse or compfy sneakers to do all the sightseeing.. no matter how ugly ur shoes are.. in most of the pics u wont see them anyway ;)
    however, i really like outfitsnumer 3 and 4, i’d wear them around for sightseeing!

    and then bring some nice flats or heels for the nightlife, there is no reason not to change ur outfit before u go out if u’re on holidays.
    in the uk people really like to dress up and wear heels, so bring some if u are able to walk in them (i’m not… :P) same for most countries like italy, spain, greece and france.
    have fun discovering europe!! xx

  4. 4
    July 15th, 2012 at 9:19 pm

    I can tell you that Converse All Stars are very popular in France, especially the classic whites!

  5. 5
    July 15th, 2012 at 10:27 pm

    This is such perfect timing! I leave for Italy in a couple days, and these are just the tips I needed! Thanks for writing this, I’m gonna wear something like outfits #2 and 3! :)

  6. 6
    July 15th, 2012 at 11:10 pm

    These outfits are amazing <3

  7. 7
    July 15th, 2012 at 11:29 pm

    These are beautiful outfits for everyday, not just touring Europe. LOVE.

  8. 8
    July 16th, 2012 at 1:41 am

    haha, i really had to laugh about the “infamously uncomfortable cobbled streets” :D of course there are many historic city centers but not all of them have these cobbled streets. actually, we have normal sidewalks in most cases, too! :D but nice outfit ideas. chic and comfortable shoes are always a plus.

  9. 9
    July 16th, 2012 at 3:20 am

    Love all these outfits! Now just wish I had a vacation… (grad school woes…)

  10. 10
    July 16th, 2012 at 5:19 am

    I love the looks!

    But I wouldn’t go walk around in the shoes from outfit 2…your feet need some support!

    But aaah these looks are amazing, I want to try them all out :D

  11. 11
    July 16th, 2012 at 6:26 am

    I love outfit no. 1 – love all the colors together. And love the sunglasses and bag in outfit four! Would love to wear those on my summer vacation :)

  12. 12
    July 16th, 2012 at 6:29 am

    europe is not just one place it is a whole continent it frustrates me how americans refer to it as if it is one are never going to be seeing ALL of europe! also no rain coats or anything?

  13. 13
    July 16th, 2012 at 6:38 am

    I agree with Chris – the shos in outfit 2 need more support if you are going sightseeing (cobblestones!) but they would be fine in a museum!
    Like a I would also advise som rainboots and a rain coat/parka -it has been raining a lot in Scandinavia! (It doesn’t feel like July at all in Denmark) But then walking around under and umbrella with warm socks stuffed into your rainboots listening to the raindrops drumming IS a treat in itself!

  14. 14
    July 16th, 2012 at 7:07 am

    The running joke in Germany is that we’re still waiting on summer to come this year. And I know that the UK has similar weather. Very cold. Very wet. Also, I don’t think we wear as many bright colors here. I really like the outfit the author wore in the photo. All the outfits are really cute, but first and last one are really more colorful than what I see here.

  15. 15
    July 16th, 2012 at 12:34 pm

    While I won’t be visiting Europe anytime soon, I simply love these outfits for any sort of traveling! I especially love the mixing of patterns in both the first and second looks. Such a wonderful post!

  16. 16
    July 16th, 2012 at 12:47 pm

    I love a great bootie that you can take through the seasons. I just bought the cutest zip up ankle booties from Chinese Laundry that I am wearing denim cut-offs for the summer and plan on wearing them with leggings and tights in the winter.

  17. 17
    July 16th, 2012 at 5:50 pm

    a – I think many Europeans think the same thing about the United States, even though it’s one country it’s extremely diverse in terrain, temperature, and culture. Like Europe, there is no way you could see the entire thing in one trip (unless you have a very long holiday.. :) )

    I agree with some of the other posters that most of the shoes are not comfortable enough for a touring trip. This is even more true if you’re backpacking since you’ll also be carrying all your stuff with you!

    When I went (in early Spring) I had plain black leather Teva boots that weren’t the most fashionable thing on the planet but they were comfortable and only started hurting near the end of a 6+ mile day touring a major city. In the summer I’d go with some plain hiking sandals, then you probably only need 1 or 2 pairs of shoes. You need room in your (limited!) baggage for all your fab souvenirs!

  18. 18
    July 16th, 2012 at 6:52 pm

    For a lot of walking, I love well-worn shoes; leather sandals (or flat boots) that have really become acquainted with the soles of your feet. Or you could get like hiking shoes (:/)

  19. 19
    July 16th, 2012 at 7:59 pm

    Unless your shoes are well broken in you’re going to want to wear Chucks or boots around town. Sandals are cute, but you’re going to be walking A LOT, even if it’s not on cobblestones, and you need shoes that are going to support you. The first few weeks I was in England I had to retrain my body because without my car I was walking absolutely everywhere and I had the worst blisters just from wearing flats around.

  20. 20
    July 16th, 2012 at 10:54 pm

    The shoes in 1 & 2 would not really work for me. I came back with only one pair of shoes after 3 months in Italy and they were more supportive and well put-together than those. Those are cute outfits, but I would also be careful about dress length, and having an optional shawl and/or jacket for going into churches. Many (if not most) will not let you in a church if you are dressed inappropriately.

  21. 21
    July 16th, 2012 at 11:49 pm

    Don’t forget a sweater or scarf to cover your shoulders when you got into churches or cathedrals!

  22. 22
    July 17th, 2012 at 10:39 pm

    While I love these outfits, I have traveled all over Europe and can tell you adults do not wear shorts there. Now, in Italy and Spain it can get pretty hot so I understand wearing shorts, but skirts or even capris would be more appropriate. In places like France, Germany, and England where it is a lot cooler, just wear pants. You’ll fit in better and look like an adult. :)

  23. 23
    July 20th, 2012 at 11:25 pm

    I spent 2 weeks in Europe last month for vacation. My sister and I really only wore our TOMS shoes because they’re so comfortable! I agree with the posters above; comfortable shoes are a MUST. You don’t want to waste the precious moments you have in Europe sitting down because your feet ache so much.
    My sister brought her TOMS ballet flats and, as cute as they were, did seem as comfortable as my TOMS slip ons. I only wore those, so I broke them in pretty quicky. Also, for packing, I color coordinated ALL of my clothes so that each piece would match with the other one. My shoes even played into that color coordination. (They were beige, and my color palette was pink, black, white, grey, beige, brown)
    I hope that anyone going to Europe thoroughly enjoys their stay. It was a magical experience! BRING GOOD SHOES! :)

  24. 24
    July 31st, 2012 at 6:19 pm

    Thank you all so much for your feedback!

    Overall, what you will be doing while touring and where you will be will obviously play a HUGE factor in what to wear.

    Although I find some of my favorite sandals (that I wear to death & therefore they fit to my feet perfectly) comfortable enough for my sightseeing purposes, others might not have the same experience.

    What’s important is to find what would work for you. You could easily switch out the sandals in Outfit #1 for some sneakers & even Outfit #2 for an unconventional look.

    And in terms of the colder weather, thanks for the heads up for those of you living in the chillier areas of Europe right now. It was cooler when I was there, too. I guess I was hoping (for everyone’s sake) that summer had finally arrived.

    If your weather forecast predicts gloomy skies and low temps, try a look like Outfit #3, swap out the shorts from Outfit #1 for pants, or add some tights to Outfit #4. And if you need a jacket, try something like a versatile tan anorak that would work with any of the looks pictured. With a little tweaking, you can find a comfy look that matches your personal style, comfort, and itinerary!

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