We’re headed to Sicily in a few weeks. It’s going to be hot (Italy in August and all of that) but we’re all seriously excited. It seems to be the sort of vacation that doesn’t necessarily need a ton of pre-planning…once the tickets were bought and the AirBnb was found….Our only plan is to wander around, eating and drinking and leisurely exploring.

I was doing a little research into what to pack (as I do), and I noticed the same advice coming up over and over again: In Italy, (Sicily especially) women wear high heels.

I am always skeptical of this advice (people erroneously claim the same thing about Paris and NY and for the most part no, no we do not) but despite the wide variety of sources I checked, the ‘wear high heels’ seemed very consistent. At least for going out at night. Which, OK. Dinner heels.

My plan, then, is to basically wear cute dresses and comfortable flat shoes during the day — much like I did in Greece last year — and then to swap out my flats for a low, walkable-yet-sexy heel when we go out to dinner.

So this became a challenge of sorts: comfortable, walkable heels…that are sexy enough for Italy?

I’m obviously not going for ‘comfort shoes’ here (sorry Linz)…instead I focused on sexy shoes that are just comfortable enough.

Most were terrible. I mean…really horrible, cut-my-feet-with-a-single-step bad. But guess what? After trying on what felt like a zillion hit-or-miss pairs (and literally throwing any sort of a budget out the window)…I found three. And while two of them are pretty pricey, one is not, and they all beat out the truly expensive pairs.

NOTE: One pair to consider (not mentioned below) is Rebecca Minkoff’s Capriana Sandal. You may recall that I can literally walk a mile in these shoes (original article here). The only reason they’re not coming to Italy with me is because they’re silver…and I really wanted something more subtle (tan, black, etc.,). 

Comfortable, Walkable-Yet-Sexy High Heels: Top Three

1. PAIGE Francesca Slides

Sexy high heels are easy to come by — but comfortable heels for travel? Harder. We're trying Naturalizer, PAIGE & more for the perfect shoe for Italy.

I’m becoming a seriously big fan of PAIGE footwear. I’m still really happy with their snakeskin boots, and now these. The PAIGE Francesca slides have a low heel with a sexy shape (round!!), and the upper is the softest-ever suede. It’s so soft (at least in this color) that I actually thought it was fabric.  

The shoes hug my feet — no sliding around — and they’re surprisingly easy to walk in. The only downside is that because the fit is snug, someone with a wider toebox might want to get them stretched. (But frankly, the leather is so soft that I suspect they’d stretch out pretty easily.)

Sexy high heels are easy to come by — but comfortable heels for travel? Harder. We're trying Naturalizer, PAIGE & more for the perfect shoe for Italy.

sunglasses | dress | shoes

2. Loeffler Randall Slides

Sexy high heels are easy to come by — but comfortable heels for travel? Harder. We're trying Naturalizer, PAIGE & more for the perfect shoe for Italy.

These Loeffler Randall Emilia slides have been around for years (in fact, Amy Voloshin was wearing a velvet pair at our launch party last week) and I can see why: they’re shockingly comfortable and easy to walk in.  They also come in a higher heel, but I really like the low heel. Sexy high heels are easy to come by — but comfortable heels for travel? Harder. We're trying Naturalizer, PAIGE & more for the perfect shoe for Italy.

They’re also available in a ton of fun patterns and colors (see the full range here)…which means that sometimes you can find one on sale. If you’d like to be notified if any go on sale, I tried to round up various retailers below:

3.  Naturalizer Kinsey Ankle Strap Sandal

Sexy high heels are easy to come by — but comfortable heels for travel? Harder. We're trying Naturalizer, PAIGE & more for the perfect shoe for Italy.

Full disclosure: I could do without the subtle glimmer. That said, these Naturalizer ankle strap sandals are some of the softest heels I’ve ever worn. The heel height is perfect, and they are so comfortable, they put all others of this style (including Weitzman’s (below) and the Sam Edelman Patti sandals we all have) to shame.  TO SHAME.

Sexy high heels are easy to come by — but comfortable heels for travel? Harder. We're trying Naturalizer, PAIGE & more for the perfect shoe for Italy.

sunglasses | dress | shoes

 

Comfortable & Sexy Heels: The Runners Up

1. Alexandre Birman Clarita Block Sandal

Sexy high heels are easy to come by — but comfortable heels for travel? Harder. We're trying Naturalizer, PAIGE & more for the perfect shoe for Italy.

Aren’t these Alexandre Birman sandals gorgeous???? The ankle ties stay tied better than expected (at least in my at-home test) and they’re very soft and comfortable. But I was worried about the tie in the long run and they’re $600. Soooo…yeaaaah…no.

2. Naturalizer Tinda Sandal

Sexy high heels are easy to come by — but comfortable heels for travel? Harder. We're trying Naturalizer, PAIGE & more for the perfect shoe for Italy.

I can get on board with *almost* all of Naturalizer’s sandals. This leather pair — the Naturalizer Tinda — is great. It’s not quite as soft as the suede pair mentioned above (that’s a really high bar) and the heel wasn’t as high…but this is a really solid option.

3. AGL Ankle Strap Sandal

Sexy high heels are easy to come by — but comfortable heels for travel? Harder. We're trying Naturalizer, PAIGE & more for the perfect shoe for Italy.

Aren’t these cool??? These AGL ankle strap sandals are insanely comfortable, and come in a bunch of unique color combinations. The best part? They basically feel like wearing flats. I ended up going with a slightly higher heel, but these are pretty amazing.

The Shoes I Wouldn’t Recommend

Sexy high heels are easy to come by — but comfortable heels for travel? Harder. We're trying Naturalizer, PAIGE & more for the perfect shoe for Italy.

Well…these Stuart Weitzman sandals pissed me off. I was all ready to take the plunge and then….they’re basically no more comfortable than my Sam Edelman Patti sandals. And they’re not nearly as comfortable as any other sandal in this list. 

The sandals that almost cut my foot when walking? This pair from Tory Burch. Which is crazy, because these sandals also have several glowing reviews. Baffling. It just goes to show how different we all are.

Anyway, I hope this helps!! And I’d love to know if anyone else has sandals they swear by…ones that are both sexy and actually comfortable. I ended up being pleasantly surprised by my search, so have some high hopes for yours… 

xo,

S

11 COMMENTS

  1. I just got back from a week tooling around eastern Sicily, and I’m happy to report that it’s pretty casual everywhere. Wedges and a casual summer dress worked well at every place I went for dinner — but happily so did cut offs and a silk cami. It’s very hilly — and HOT! — but gorgeous. Have so much fun, eat lots of granita and drink lots of wine from Mt Etna!!

  2. Having lived in Italy for four months, I would highly recommend more of a block style heel. Many streets are cobblestone and thin heels easily catch between the stones. Hope you have a great time!

  3. We spent a week in Sicily (Catania and the area around Catania) in June. It is unbelievably gorgeous. I second everything Danielle said – the granitas (oh my goodness, they are amazing. to be super Sicilian, get a brioche with your granita); the Etna wine is unbelievably good for the price, as is the Etna Amaro; and I didn’t notice women wearing tons of heels. Honestly, I saw a lot of flat sandals (like totally flat). I even bought a pair in Taormina because they were handmade and to feel more like the other women I saw in Sicily. Also, many of the streets are cobblestone, so be extra careful with skinny heels. Also, Sicilians eat dinner/go out later than we typically do – generally between 9-10 at night. As our Sicilian babysitter explained to us, Sicilians are very laid back. They’re not rushed to do anything. If you are near Taormina or Syracuse, consider visiting the Roman/Greco amphitheatres. They are magical and amazing. And, a boat tour of the caves in Syracuse is also recommended. Our six year old daughter considered it the highlight of the trip. If you go on the boat tour, wear a swimsuit – you get to jump in the water and swim at the end of the tour. We didn’t know this and were scrambling to buy swimsuits before we went on the tour (my daughter is still wearing her “Italian bikini” that she loves, so maybe it was fine). Have a wonderful time! I’m so excited for you!

  4. It’s been decades since I’ve been to Southern Europe, but friends have confirmed that my advice was on point: walking around the city streets requires flats or block heels as mentioned, but also the streets can be very dusty and dirty. I often had dirt up to my ankles at the end of a day in Italy or France. No judgment at all regarding these cities—it was fabulous, and I’m dying to get back, especially to my ancestors’ home near Sicily—but my advice is to wear shoes that won’t look dirty or get ruined by the dirt on the streets. Any recent travelers who can confirm?

  5. Ugh, wish I had waited a week to order the Stuart Weitzman Simple Sandals — they arrived yesterday and I found the same thing as you, not comfy. I think the suede version is better though, because I had tried on the same style in black suede at a Stuart Weitzman store and they were much softer.

  6. Lived in Sicily for two years (2001-2003), and just got back from a two week visit. My husband and I could not get over how casual the Sicilians have become. Our Sicilian friend was wearing cargo shorts! People walking around in gym wear! Women in shorts! Not a lot of heels, but heels are fun, so bring them if you have room in your bag.

  7. So, so excited for you! We lived on Sicily for a few years and absolutely loved it! The food!!! The wine, the olive oil, the sights! We still miss it. Can’t wait to hear what you think. xo

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