March 28, 2018 - Easy Outfits, I Feel Pretty, Style

Best Shoes for Spring Break in Italy

Warning:  The following post is loaded with vacation pics!  We’re fresh off our spring break trip to Italy and I’m finally catching my breath enough to write a post about it.

I promised to give you a few style (and footwear) pointers from our experience, which I’ll get to later, but first up some pics from our time there!

Two years ago, we explored Rome and the Amalfi Coast so this time we headed north to Florence and Tuscany.  It was an eight day whirlwind but we saw and did A LOT.  We explored as many of the Tuscan hill towns as we could fit into our schedule – including Siena, Pienza, Montepulciano, Pisa, Lucca and San Gimignano plus a few others that I’m probably forgetting.  We stayed in the Chianti region so did tons of exploring around there too.

First stop Florence!

Moving on to Siena where we caught the last day of a chocolate market with artisans from all over Italy.  Serendipitous indeed!

We ate gelato everywhere, lots and lots of gelato!

Decisions, decisions…

A sunny day in picture perfect San Gimignano.

Silly girls at the train station.

The highlight of our trip – a perfect day in Cinque Terre.  The sunset at Riomaggiore was magical!

Our last night we had a wine tasting and pasta making class in a castle built in the year 1084. The family who built the castle had their coat of arms above the door created by Donatello. I’m a total art history nerd so this was the highlight of my night.

A beautiful day for dining al fresco in Lucca.

Stopped by Pisa, got the pic!

Now onto the style!

I’ve been asked for my packing list quite a few times which to be totally honest consisted of five pairs of jeans, tops for layering, three jackets and two scarves. Not all that interesting but totally functional! It didn’t really matter because my jacket kept my outfits covered most days.

The most asked question I got was,

What shoes did you wear in Italy?

I honestly wasn’t quite sure what I was going to wear beforehand.  I took a pair of ankle boots, three pairs of sneakers and a pair of riding boots. The ankle boots never came out of the suitcase but I did wear the heck out of the sneakers and riding boots.

Best Shoes for Italy Trip

My New Balance sneakers were my go-to on days with lots of walking. I wore them with no-show socks.

New Balance 220v1 Sneakers

My Dr. Scholl’s slip on sneakers aren’t quite as comfy so they weren’t my first choice for lots of walking. But they did work well with a pair of sock liners.

Dr. Scholl’s ‘Scout’ Slip On

My riding boots were my first choice when we weren’t doing a lot of walking and I wanted to dress a little nicer.  My exact boots are a few years old and sold out but these are similar pairs.

Gray Riding Boots

In case you’re wondering if I was the only American tourist running around Italy in sneakers, the answer is a resounding NO.  ALL of the locals wore sneakers so I felt right at home.  I took these snaps of some of the shops in Lucca to show you just how prolific sneakers are in Italian fashion for both men and women this spring.

Are you on the sneaker bandwagon yet?  If so and you want to pair your sneakers up with cute spring outfits, then join me for the Style Challenges Spring 2018 Capsule Wardrobe!  You’ll get your shopping list of spring basics and trends plus 31 days of mix and match outfit ideas – including a few cute sneaker looks.  Learn more and sign up HERE.


It’s the day of the week at GYPO where we celebrate what makes us feel pretty. Whether it’s a new outfit, hairstyle, or makeup, the I Feel Pretty link up is about anything and everything that makes your life prettier. Even if you’re not a blogger, you can still play along. Just tell me what made you feel pretty this week in the comments.

There are just a few simple rules:

1. Follow GYPO. (Bloglovin‘, FacebookInstagram or Pinterest)
2. Link up your pretty post.
3. Link back to GYPO.
4. Visit other pretties!

Get Your Pretty On diagonal divider

Get your free Closet Staples Casual Capsule Wardrobe shopping list + four free outfit ideas!

  • This field is for validation purposes and should be left unchanged.


  1. How fun! Your post brought many memories back of when I was in Italy about 7 years ago. I went to Florence and Pisa too. Except, I don’t remember locals wearing sneakers. You could always tell the tourists apart from the locals, because Italians always dressed so nice. They take such pride in their appearance and clothing. Whereas the tourists, especially Americans, dressed casually.

  2. Can you share which no show socks you wear? Never have found a pair that stay on. Gorgeous pictures.

  3. This is very timely for me as we fly out to Rome on Sunday for two weeks in Rome, Pompeii, Amalfi and Puglia. We are in the UK and have been to Italy the last two years, once at Easter time when it was very warm and I’m thinking it won’t be as warm this time, so was interested to see your pics with your jackets and jeans on. We are taking carry on luggage only so shoes are a particular challenge! “sneakers” (we call them trainers) are big fashion news over here at the moment, particularly the white leather style slightly smarter style, rather than running shoes, although Nike Air Max are big on the blogs at the moment

  4. Thanks so much for sharing! When I did Europe I felt sooo touristy (must have been the maternity clothes because it was our baby moon). I like the simple tip of sneakers with no-show socks – looks trendy and not ugly american touristy. I will have to implement this everywhere I go this summer that requires walking, even if it’s just in the Americas! Also, gorgeous pic of your family at Cinque Terre. Thanks for sharing a little bit of your family life!

  5. WOW! What an awesome trip and experience for your girls. I loved the pic of them at the potties. Too funny! Of course you ate lots and lots of gelato. When it Italy…

  6. LOVED SEEING your your picture as you were living it. I bought it pair of tennis shoes to wear with outfits and my husband says, so you bought a pair of workout shoes to wear for fashion. I said yes, he gave me the side eye. Haha!!!

  7. This is perfect timing! I’m touring D.C. with hubby soon and am looking into comfy shoes! I ordered a couple of Croc slip ons since I think they will go with most of what I wear, but I like the idea of sneakers when the footies really get tired 🙂 Especially being preggo. Thanks for sharing about your lovely family trip.

Comments are closed.