6 Pairs of Shoes That Kept Me Warm, Cozy and Comfortable in Italy

For several weeks before my trip to Italy, I checked the “extended” forecast for the Tuscany and Amalfi Coast region a couple of times a week. As the time drew closer to leave, I checked almost daily. Forecasts can often be wrong but the three-week extended forecast for the areas we were to be touring, was consistently showing chilly temps and cloudy days with lots of chances for rain. Ugh. Not what I wanted to see.

I am cold-natured and I hate with a passion having cold feet. I especially hate having cold, WET feet. If my feet are cold, I’m miserable. I waited until the week before the trip to get serious about travel-shoe shopping. Once it looked like the forecast was going to hold true, I threw it in high gear and went on an all-out hunt for shoes that would be great for cool weather, especially cool, rainy weather.

Several times during the trip I gave myself a silent pat on the back because the shoes I took with me were absolutely perfect for the trip. My feet stayed warm and comfortable; I could have walked forever in the shoes I took on this trip. And through all the rain, some that lasted all blooming day long, my feet stayed cozy, warm and dry.

Today I thought I’d share the shoes I took on the trip because they aren’t just shoes that would be great for traveling and touring, these are shoes that  you can wear all fall and winter, even into spring. I will be wearing them all this fall and winter and hopefully next year, too.

These shoes shown below are the shoes I took on my trip to Italy. I also took a pair of tall, low-heeled boots but only wore them once so I didn’t include them in this post. I took one pair of dressy heels purchased many years ago, to wear the night of our farewell party. We dressed up a bit that night and the heels took up very little space in my suitcase, so I brought them along though I only wore them for that one night.

Great Shoes for Fall and Winter Travel


The shoes and boots you see below I wore A LOT! All were super comfortable, the kind of shoes you can walk and walk and walk in all day long. Even though several pairs were new, they fell under the category of “comfort” shoes and comfortable they were. I also wore the new ones around the house for a day or so to make sure they would be trip-worthy.

I’ll share each style/brand and link out to where I purchased them in case you are interested in buying a pair for yourself. All of these were purchased before the trip but not just for the trip. I badly needed winter shoes so the trip gave me the push to shop.

5 Great Shoes For Travel


Starting on the far left, the black pair with the top stitching is the only pair I can’t link to for you. They are “Natural Soul” by Naturalizer. I don’t think I’ve ever had an uncomfortable pair of Naturalizers so I wasn’t surprised when I tried these on at Marshalls and found they were super comfy. I can’t remember how much they were now, but I remember it was very reasonable. I normally wear a size 7 and that’s what size I took in these. They zip up the front which is really cute. I noticed another person on our trip wearing them, only she wore them unzipped.

Shoes for Travel


Continuing across from the left, I’m not normally a “bootie” fan but these shoes converted me. I wanted a low pair of boots to wear because I thought they would keep my feet warm and be good on some of the rainy days. I went with black since I was taking several pairs of dark-colored pants, including black and navy cords.

5 Great Shoes For Travel


Here’s a picture of the boot in brown. I’m sharing it in this brown color because it’s hard to see the style/design of the shoe in the black color. These boots have excellent arch support and they were AMAZING! I wore them on the day we toured Florence and it rained the ENTIRE day. We’re talking downpour ALL the blooming day long. My feet were totally dry the entire time.

They were a little pricey but were worth every penny. I could have kissed these boots when I got back to the hotel because I would never have made it through all the walking we did in the constant rain in Florence without them. They are by TEVA and I purchased mine at Dillards, but you can now find them on sale for over 50% here: Suede Ankle Boot

Oh, I bought these in a 7 1/2, a half-size bigger than I normally wear because I always wear thick socks with boots. If you wear normal socks, your regular size should be fine, but if you wear really thick socks with boots, you may want to go up a half-size like I did.Delavina Waterproof Booties

I liked them so much, as soon as I got home from Italy, I went online and ordered them in this color, too. Update: All these boots are on sale now for around 50% here: Suede Ankle BootTeva Waterproof Booties


Another pair of shoes I enjoyed and wore on the non-rainy days were brown Skechers shown in the middle in this photo.

Great Shoes for Fall and Winter Travel



Here’s a better photo of them from online. I found them in my local Steinmart right before I left. The salesperson who helped me said they had just gotten them in. They are super comfortable and are available here: Skechers Women’s Big Bucks Fashion Sneaker

Skechers Big Bucks Sneaker

Moving on down the row, I wanted to take along a pair of shoes that had a somewhat summery feel in case we had a sunny day on the Amalfi coast. But I wanted them to work with my fall clothing, too.

5 Great Shoes For Travel


When I was shopping at Dillard’s, I purchased two pairs of Sperry boat shoes, one in a light tan color for summer and this one below in a darker color that’s perfect for fall. Since they are “boat” shoes, they work well on all surfaces, especially those that were still damp from the rainy days.

I love topsiders and am so happy that Sperry makes them in colors that work for fall. These are kind of sassy with a subtle metallic sparkle on the side and on the front. I purchased them in my standard size 7 and wore them with normal socks on the warmer, non-wet days. In the summer they would look great without socks. You’ll find them available here: Sperry Boat Shoes

Sperry Ivyfish Metallic Boat Shoes


Last but not least, the plaid rain boots you see on the far right saved my cookies more than once on the Italy trip. They are also by Sperry. I’ve been yearning for some plaid rain boots for a while and I fell hard for these when I saw them.

5 Great Shoes For Travel


Here’s a close up of them from online. Cute, cute, cute! They have a little zipper on the side that makes them super easy to take on and off, so there’s no need to tie them. I purchased them a half-size bigger in a 7 1/2, again because I like to wear really thick socks when I wear boots. You’ll find them available here: Sperry Saltwater Waterproof Rain Boot

Sperry Plaid Saltwater Waterproof Rain Boot

You can see how they look in this photo I took on the beach at Positano. Of course, it was raining then, too.  Do you like my “umbrella” jeans with tiny umbrellas all over them? lol Those are a Talbots purchase last year…got them at the end of the season on sale.

Sperry Plaid Rain Boots


Speaking of boots, I already had these L.L. Bean duck boots that I purchased last year. I love them and wear them a good bit in the fall and winter when it rains. In fact, it’s raining here today (followed me home from Italy) so I wore them today when I stepped out for a bit.

L.L. Bean Leather Shearling-Linded Lounger


I’m not sure why but L.L. Bean doesn’t seem to have this style this year. It’s called L.L. Bean Tumbled Leather Shearling-Lined Boot. Sorry I can’t link out to it. If L.L. Bean offers it again, I’ll add a link to this post. Another style I do like by L.L. Bean is THIS one. I also like that they offer free shipping, too. Glad to see so many stores doing that now.

L.L. Bean Tumbled Leather Shearling-Linded Lounger

I would have taken along my L.L. Bean boots but they are a good bit heavier than the Sperry boots and my bag weighed 48-1/2 lbs…just 1-1/2 lbs shy of the limit! I used my bag scale thingy to check it, so I knew I was super close. I was glad I had the Sperry boots for the trip. They are adorable with jeans and should work well for fall, winter or spring.Sperry Plaid Saltwater Waterproof Rain Boot

I was wearing them the day we visited Frances Mayes house. Any time I wore my jeans or navy pants, and it was raining (which was often) these were my shoe/boot of choice.  You’ll find them available here: Sperry Saltwater Waterproof Rain Boot

Frances Mayes Tuscan Home, Bramasole, in Cortona


So, these were the shoes that got me through a 17-day tour of Tuscany and the Amalfi Coast in complete comfort. They went with all my outfits/clothing and they met all my needs. I highly, highly recommend any of these shoes or boots! All are super comfortable, well-made and great for wearing on a trip or for everyday use.

Great Shoes for Fall and Winter Travel

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  1. Susan, I really love the info on your shoe selection! I may have to try a pair of the suede boots and your blue/plaid Sperry boots. Boy, could I use them here in Memphis! We’re getting days of rain from the hurricane that is devastating TX and the coast. We need the rain, and it is gentle, so I am not complaining. But it does work a number on the shoes. I am going to try your jacket you pictured weeks earlier – the one the queen wears! I have always felt a bit “princessy,” so I think I should have one! LOL! No, really, it appears to be a very versatile winter coat. Did you find it so in your travels? I did get the travel purse you showed in black and loved using it in our New England trip this past summer.

    • Martha, I couldn’t believe it when I got home and it started raining here in Georgia. I can’t get away from the rain, no matter what continent I travel to! lol Well, I goofed big time, I walked out and left my Barbour jacket and the pretty Talbots basketweave sweater I had purchased just for this trip, on the chair in my breakfast room. I realized it as soon as I got to the airport. Thankfully, I had tucked my windbreaker down inside my large bag. I ended up wearing it the whole time. It worked great since it has a hood and I don’t like carrying an umbrella. I can’t take photos and hold an umbrella at the same time, plus I always leave them somewhere. I’m going to buy the hood for my Barbour jacket. I really missed having it on the trip…I love its big pockets. But I definitely would have needed the removable hood for all the rain. That will be my next purchase, the hood to go with my Barbour coat. It is a great travel coat, when you actually remember to take it!

  2. Hahahaha, I was cracking up when I saw just the title of your post…6 pairs of shoes….you had me! But you really took 7, right? That’s hilarious to me for some reason, but I must say I am impressed. Shoes are always so heavy, you chose wisely. I really like the Teva booties and the Skechers sneaker, and have different brands very similarly styled that I wear a lot. I’m like you – don’t like cold feet.

    • Yep, I took 7! I forgot to mention it in the post, but I stuffed my undies and socks down inside all the shoes. lol So that space didn’t go to waste. 🙂

  3. Thanks for the info. I hate shopping for shoes and this really helps. Comfort is everything.

  4. Loved all the pictures you sent along the way, they brought back wonderful memories of my time in Italy several years ago. Thanks also for the information about the shoes you took. I’m certainly going to check into some of those. It’s good to have you safely home and back in the “Good Old USA”

  5. Glad you are home after your fabulous trip. I followed with great anticipation. I am in awe you were able to blog and tour at the same time. We fell into bed every night exhausted.
    Love the pics and comments on shoes. That was my worst nightmare because I have problem feet.
    Sorry about the rain. Your pics of Sorrento looked clear. Hope you got to Capri without rain. We had to take the ferry and couldn’t go to the grotto. I was a little motion sick and was very glad to get off the ferry. I think we rode on the top coming back instead of in the belly of the ferry and that was better.

    • I know what you mean…I was whipped by the end of the day. I did all the “optional” tours but one, and that day I walked for hours and hours in Sorrento. So, I never had a day of rest but I was determined to see as much as possible. It flew by so quickly!
      Thankfully, for most days, it would stop raining for a little bit so we could get a few pics…but you’ll notice on Instagram and when I eventually go through them all and post some on the blog, that there’s rarely any sun…just cloudy, overcast skies. I think we had 2-3 days with sunshine, the rest were cloudy or rainy. I was told that it normally doesn’t rain a lot in October in Italy but it sure did on our trip. I would never go to Italy in October again, even if it supposedly doesn’t rain that much in October.
      It was raining the day we went to Capri so we had to sit inside. The seats on the upstairs part were filled with rainwater. It would have been fun to have sat up there!

    • Bonnie, your mention of problem feet piqued my interest, as I certainly fall into that category, too! I wear a 10.5 narrow in most shoes, but in sneakers or sports shoes I wear an 11-11.5N. Do you know how hard it is to find those sizes? I also have arthritis-related toe problems, etc. Even on Zappos or the other online shoe sites, it’s very hard to find comfortable shoes, without 5″ heels (!), in those sizes, without going up in the $200 and up price range. I have purchased shoes from Zappo’s and Drew shoes online, as well as 6pm.com. I looked at all of the boots/shoes Susan posted, but none of them come in Narrow, or 10.5! Really cute shoes, though, Susan!

  6. Love your style, especially footwear; gotta go check these out!! Thanks for putting this post and links together.

  7. Marlene Stephenson says

    Thanks so much for all this info shoes are very important but anymore i need comfort and warmth. In the summer i could almost go barefoot but not in fall and winter.

  8. Thanks for the review, but Yowzers….that’s a lot of $$$ on shoes right before an expensive trip! Having said that, cheap shoes are just that, and there is nothing worse than being uncomfortable! I’m with you on the Naturalizers. I have the same pair in brown. They’ll last me a long time, because being a Florida girl, I dont have much occasion for closed toed shoes (so why do I have over 100 pair of socks? ) I live in Flip Flops most of the year. Also my size 10’s take up a lot more room than 7’s. If you were limited to TWO pair, which would they be?

    • Bernie, I go sometimes a 2-3 years without buying fall or winter shoes. The last few years I’ve been wearing my Uggs all winter along with a pair of tennis shoes. I can never find fall/winter shoes that I like. I mostly just buy summer shoes because I love sandals. This trip forced me to look for fall/winter shoes. I took a variety of styles because it was too long a trip to be miserable while there and I knew I’d get tons of use out of them for years to come. The black Naturalizer shoes from Marshalls were very inexpensive…either $19.99 or $24.99, as I recall. If I had to pick just two of these, I would choose a pair of the boots, probably the black TEVA boots since they will go with anything and are waterproof. For the second pair, I’d probably go with the brown Skechers, since the brown would go with things the black wouldn’t go with. It would be hard to go on a 17 day trip with just two pairs of shoes, not impossible, but I’d at least take three. Would be nice to have something more summery like the boat shoes for the pretty days on the coast.

      • Thanks for the input! I’m kind of like that when I shop for bathing suits (ugh) I’ll go 2 or 3 years, and then buy 3 or 4 at a time (usually at Marshall’s or Ross) If it fits, I’ll buy it!

  9. You’re a great personal shopper, Susan! I struggle with finding winter shoes, too. But I love the waterproof booties that you showed! So glad you stayed nice and dry on your trip!

    • Thanks, Jane! Those are awesome! I almost thought they had too much arch support when I purchased them but after wearing them a few hours, they were perfect. TEVA knows how to make comfortable shoes. I had no idea they made boots until I spotted those.

  10. Mary ellen says

    Thank you so much! I’m heading to England in March and have been looking at waterproof shoes/boots. I live in south Florida so don’t have much need for winter boots but I think I’ll invest in the Tevo boots. I love your travel tips and thanks for sharing. Happy travels!

  11. Margaret Robinson says

    Hi — I’m impressed that you took so many shoes; all that looked good and were functional. Have found over the years that we’ve travelled that a good pair of “walking” shoes is essential and I wore out a pair that had a zipper instead of laces I bought for Italy.

    However and I hope I’m wrong about this – you didn’t buy any Italian shoes? You were in the land of gorgeous, fabulous, unique and wonderful women’s shoes! One pair would have done it and it would have meant a new pair for your next trip besides.

    • lol No, I’m not sure I would have had room for them in my suitcase. I did pass a lot of leather stores, though. I didn’t go in any. They probably would have been wasted on me since I wear almost nothing but very casual shoes these days.

  12. Susie Hinson says

    I’ve thoroughly enjoyed your trip to Italy! Thank you so much for the postings and photos. This post about the shoes you took was very informative for all of us planning trips overseas or in this country. I have very small feet so have a terrible time finding quality shoes that feel good on my feet. I’ll check out all of your recommendations. I’m so glad you had a wonderful time and shared it all with us!

  13. Cyndi Raines says

    Glad you are home Susan and thanks for the tips from the other day on fixing water hoses and now this on the shoes /boots. I agree, cold feet are the worst and living in MI it can happen fast. Love the look of the Teva boots (have pinned those) and of course the duck boots / Sperry Saltwater plaid boots. My boat shoes get a lot of wear in the summer when my feet need extra support and have to pass on the sandals, but they are my favorite.

    • Thanks, Cyndi…it’s good to be back. Just wish the rain hadn’t followed me home. Ironically, my trees on my deck were looking pretty parched with dried up leaves and then it starts raining AFTER I get home!
      I bet you do get tons of use from your boat shoes with those wonderful lake trips. The rest of us are wearing them in hopes the lake will come to us. It’s fun to dress the part even if we aren’t there. 🙂

  14. Linda Palmer says

    Hi, Susan! I’ve enjoyed your Italy trip posts so much. I like all your shoes and am glad they served you well. I think my favorite pair is the black Naturalizers with the zipper. If I were travelling I would want a pair of your plaid rainboots for sure! Welcome home, and I’m looking forward to all your holiday posts–my favorite time of the year!!

    • Thanks, Linda! I noticed that the stores have begun putting out all the Christmas goodies now. Time to start thinking about the holidays around here! I ran over to Wally World last night for something and took a spin through their ornament section. I was surprised to see they have a lot of the ornaments I’ve used in tabletops back in again this year. I took a few pics and will share those soon in case anyone wants to use them, too.

  15. Shoes, shoes, glorious shoes …. ! I’m remembering in one of your earlier posts that you showed us (a) photos of the bags you’d be taking and, looking at the number of shoes that you took on this trip, just how did they all pack inside that/those bag(s)? 🙂

    • lol I think you’re thinking of the bags I had to use for the trip to Africa when I was so limited due to flying on little planes over there. Fortunately, on this trip, I was allowed a full size bag plus my rolling bag. I’ll take a photo of the bag I used and include it in a post sometime soon. It’s a large, plaid,London Fog bag I purchased in Marshalls several months ago in anticipation of traveling in the future. It was stuffed to the max. It’s hard to pack for 17 days. I never had to do laundry the entire trip, although some folks in our group did. I didn’t want to waste a precious moment in a laundromat…not the part of Italy I had any interest in seeing. 🙂

  16. Mary from Virginia says

    welcome home ! The lesson on shoes and the links are much appreciated!

    I am in need of shoes.

  17. I enjoyed tagging along on your trip to Italy! Totally agree with you about the Naturalizer brand..most are comfy. I just discovered the Work collection of shoes from Naturalizer. My first pair is so great for dress or walking. I am getting another pair soon! The fact that I wear a 4.5 size automatically eliminates me from so many brands! boohoo. Thanks for sharing your shoes. Women and shoes…ha!

    • Yes, women and shoes! We do love them, don’t we. Sheila, what is the smallest size they make? When I wore a 6 1/2, I could occasionally find summer sandals that I liked in the children’s section. They were less expensive, too.

  18. Hi Susan, I loved your post on the super shoes you took on your trip! I dislike cold, wet feet too, so I read with interest what you said about each shoe/boot. This was great info!! I’m going to order a pair of Sperry boots like yours and I am so looking forward to dry, warm feet!! Thanks for taking the time and pictures to help us with our comfort needs!! I loved your cute *Here I am!* picture with your neat umbrella pants!! Thanks for the great post! 🙂

  19. Hi Susan,

    I thoroughly enjoyed this post – you have given such useful and practical advice that many of us can apply to our future travels. I for one am always searching for a good shoe that will save me from cold and wet feet! I’m definitely going to check these out – especially the TEVA booties. You have a wonderful blog – this is the first time I’m submitting a comment but I love everything from simply the name of your blog, to your ideas about decorating, your travel posts, just about everything! Thanks for creating something that so many of us can learn from and enjoy!

    • Thanks so much, Sharon…appreciate that so much! I do love those TEVA booties. I didn’t even know they made boots until I found those. They are awesome!

  20. When we went to Rome several years ago, most of the Italian women wore high heels. We were touring and walking on all those brick/cobblestone roads and they would walk right by in there heels. They must be some tough women.

  21. Susan this is a timely post for me..thanks. I have a trip to Europe scheduled for the spring and shoes are a priority. About the skechers-I have had two pairs and while it is almost impossible to wear them out to the point you have no qualms about discarding..for comfort sake I found they must be replaced at some point if they get heavy wear. That said-I love them they feel like a soft kid glove hugging my feet. So that’s on my list before my trip-perhaps the end of the year -time to wear a while before the trip. I too am planning to add a pair of the low heel [booties] boots in black leather- unless some gives me good reason not to include them. I had thought of a nice [colorful?] flat slip on for a dress up shoe. What do you think?I am thinking the flat would take up less luggage space?

    • Jonell, that’s how I felt…shoes were a bigger priority for me than the clothes I was taking…’cause if your feet aren’t happy, you aren’t happy! lol I had a older pair of Skechers that I had worn so much, they had cracked at the point where they naturally crease from the bend of the foot. I still wouldn’t throw them out because I couldn’t find any I liked as well. The brown ones I purchased or very similar so I just finally tossed my old pair a couple of days ago. I still wish they made the old style that I just tossed, but they don’t.
      A flat slip-on type shoe should work great for that. The somewhat dressy pants I wore the night of our farewell dinner are a tad long (I need to get them hemmed) so I needed a shoe with a heel. That’s the main reason I took the highheels on the trip. Ironically, that night our dinner ended up being in a restaurant several blocks away form our hotel. It was no fun walking 4-5 blocks in those heels! lol So, go with flats when you can.

  22. pam ~ crumpety cottage says

    Good info, Susan. I particularly like the Sperry rain boots. So cute! Those Teva suede boots are pretty nifty as well. Thanks for the suggestions. 🙂

  23. Love those Teva boots. It’s all about comfort when traveling!

  24. Thanks for your advice and recommend shoes for comfort and walking. I have an upcoming trip planned to Florence,Rome and Venice…And hopefully Amalfi Coast (may need to stay extended time–hopefully!) sometime in April
    Would you still recommend the same type of shoes? Rain boots? Do you suggest any other shoes more appropriate for Spring?

    • Lisa, check to see what the rainfall and temps are normally for that time of year…you can just google it to see. It the temps will be chilly, I would definitely take some kind of rain boot if you see that they usually get rain during the time you’ll be there. The plaid ones were comfortable enough to wear and walk in all day. I’ve been wearing them a lot since I’ve been home and I forget to take them off when I’m home, they are that comfortable.

      If the weather looks like it will be warm during the time you’ll be there, I’d wear a comfortable but practical sandal like the ECCO sandals in this post: https://betweennapsontheporch.net/how-to-pack-for-an-african-safari/

      They are the most comfortable sandals I’ve worn ever! They can get wet and it doesn’t hurt them at all. They are rugged and they fit your feet like a glove. I love them! Just read the reviews at that link in the post and you’ll see how awesome they are. When I’m at home, I wear strappy little delicate sandals during the spring/summer, but if was going to be walking all day touring, I’d go with something practical like the ECCO in that post. Here’s a link where you can see/read about the ECCO sandals: http://amzn.to/1kxnElC

      If it’s not going to be rainy, and you’ll be wearing pants a lot, the other shoes in this post would work great, too. I saw tons of folks on the tour I went on wearing tennis shoes, so ignore all the stuff you see online that says you shouldn’t wear tennis shoes. You’ll see LOTS of folks in them when you’re in Italy. It may be mostly the tourists who are wearing them, but who cares, you want to be comfortable. And you’ll be surrounded other who are wearing them. So if you like tennis shoes, by all means wear those.

      You can check the extended forecast for Florence or Rome before you leave and see what is predicted for up to three weeks out, so just look about three weeks before you plan to leave and you’ll know what the weather and temps will be, and then you’ll know what to take. Hope this helps.

  25. I’m so glad I found this, and thank you for your posting!! I’m going to Italy (Milan, Venice, Florence, Rome) at the end of this month to mid January and was so worried about what shoes to pack. I am all for comfort yet don’t want to sacrifice style. I think the Teva Delavina boots and Sperry duck boots are awesome! Thank you for the tips~!!! Very much appreciated.

  26. Great shoe choices! And yes, it was a very wet and chilly fall this year. I just may direct clients to your site to get a good visual on some footwear ideas!

    -Catherine –
    Vitalia Tours

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