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The 6 Types Of Comfortable And Cute Shoes We Want To Wear On Vacation

I am famously horrible at packing for vacation. Not only do I do that thing where I bring the most random articles of clothing that I haven’t worn in years, I also tend to bring 5-6 pairs of shoes with me no matter where I am going. I’ll be going to Hawaii and I’ll bring cowboy boots. It’s like as soon as the word vacation enters my brain, it acts like it has never heard of getting dressed before. Of course, I hear via lifestyle influencers on TikTok that the goal is to pack light by planning outfits you will actually wear, according to the vacation you are going on. A novel idea! But I have truthfully always struggled with what shoes to bring on vacation so I asked Emily to weigh in on the matter:

“I like to pack light so I’m into versatility rather than bringing 6 different sandals. The Madewell ones that I bought last year are casual, super comfortable, but easy to dress up. My tkees flip flops can go easily beach/pool to dinner (plus they are tiny, so easy to pack), and then one pair of wedges if we get a sitter to go out on a date (but still needs to be comfortable – like my new espadrilles with the white rubber sole). And then I love a pair of more active shoes for walks, hikes, or water play.”

With Emily’s expert advice in mind, we rounded up the shoes we want that fit the bill for a vacation:

1. Fisherman Platform Espadrille Sandal | 2. The Julie Espadrille Sandal | 3. Satara Platform Slide Sandal | 4. Marli Strappy Espadrille Flatform Sandal | 5. ALOHAS Leather Back-Strap Espadrille Sandals | 6. Cameron Flatform Sandal | 7. Espadrille Sandal Wedges | 8. Adea Wedge Heels | 9. KAANAS Medan Buckled Cotton Espadrille Sandal

Espadrilles are a famous vacation shoe. They are great because they are casual but still cute enough to wear to pretty much any outing. They go from day to night easily so if you are spending the day at the beach or by the pool and then you are ready to transition to dinner, there’s no need to swap shoes. I love #9 because any shoe I can slide right into is my ideal form of footwear. Emily just got #6 and says they are extremely comfortable and cute enough to wear to dinner.

1. Baminda Wedge Sandal | 2. Josiey Sandal | 3. Julianna Platform Heels | 4. Kali Wedge | 5. Silent D Katia Wedges | 6. Otis Wedge Sandal

I’ve been waiting for a reason to wear wedges because I do love heels I just have no clue how to walk in them. So I need the extra support that wedges graciously give. If you know you will have a night out on your vacation, Emily suggests a wedge because they are comfortable but are still technically heels so they feel date-night appropriate. I am very interested in #1 for its sole that looks extra comfortable, but #4 is what I want to wear to a romantic ocean view dinner with my fiancé. And how cute is #5??

1. The Maggie Sandal | 2. Go-To Flatform Sandal | 3. Wiwiel Platform Sandal | 4. Santa Monica Sunrise X-Band Leather Platform Sandal | 5. Jonah Slingback Sandals | 6. Monroe Platform Sandals | 7. The Addie Sandal | 8. Dandra Leather Platform Sandal | 9. Pacific Sandals

If wedges are a little much or if you have a good amount of walking to do, flatforms are our favorite alternative. They still give you some height but the straight platform makes them more comfortable to walk in. A flatform sandal is a good option for a day on vacation where you’ll be walking around shopping or sightseeing, but still want to feel cute and pulled together.

1. Fisherman Sandals in Shiny Spazzolato Leather | 2. Marina Leather Fisherman Flat Shoes | 3. Fisherman Sport Sandals | 4. The Fisherman Sandal | 5. Pilcro Casual Gladiator Sandals | 6. Chunky Leather Gladiator Sandals

The fisherman sandals are the casual, edgy cousin of the espadrille. They can just as easily go from day to night, but are more appropriate for like, grabbing a burger after a long day of window shopping on the boardwalk. I like a shoe with some extra sole support so my top picks are #3 and #6, but I really like the simple look of #1.

1. Hurricane Drift Teva | 2. Holden Platform Sport Sandals | 3. Birkenstock® Arizona EVA Sandals | 4. Salt Water Original Sandal | 5. Shibui Cat Sandals | 6. Jadito Universal Sandal | 7. Classic Clog | 8. Hurricane Verge | 9. Neida EVA Two Band Slide Sandals

Utility sandals should be comfortable enough that you can walk, hike, or do water activities in. They are usually waterproof or water-resistant and have a lot of support so you can comfortably be active in them for hours. You won’t want to do rigorous adventure activities like rock climbing in them, but if you are planning on a lot of walking near water, these are great options.

1. Kashiba-Lux Print Slide | 2. Puma Shibui Cat Slide Sandal | 3. Inuikii Braided Leather Slide Sandals | 4. Beach Bum Slide Sandals | 5. APL Big Logo TechLoom Slide Sandals | 6. Alix Kashiba Slide Sandals

This is my favorite category of shoe, vacation or not. I am just so into the ease and comfort of slides. I think they are really cute with shorts or jeans or even dresses, and you really can’t beat the ease of slipping them on and going. I currently have a pair of Adidas slides that I’ve worn to shreds so I am thinking about upgrading to a more fun, colorful version. I do love checkers so you know I am eyeing #3, but #2 look widely comfortable and that’s hard to resist in my eyes.

So those are our current vacation shoe picks, but if you have any that you can recommend please drop them below. And if you have any packing tips for a chronic over-packer, I am all ears! xx

Opener Image Credit: Photo by Veronica Crawford | From: The Fun, Easy To Wear And BOLD Dresses I am Opting For This Summer

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2 years ago

For warmer holiday destinations I usually go for 1 pair of practical sandals (Teva<3), 1 pair of pretty leather sandals and 1 pair of closed shoes (sneakers or comfy ankle boots). Oh and flipflops if there is a beach of pool involved!

2 years ago

I absolutely love Viscata espadrilles. They’re on the spendy side, but they’re comfy, wear really well, require zero breaking in, and go with everything.

2 years ago
Reply to  Anne

I like the fact that they’re made in Spain!

2 years ago

I am a dedicated minimalist packer, and my hands-down favorite vacation sandals are the classic saltwaters (Hoy brand). Even though they’re leather, they’re made to get wet, dry out, and be totally fine. So, they do double duty as utility sandals and vacation sandals. I’ve worn them straight from kayaking/tubing to shopping / going out to lunch. And, if they get dirty you just hose them off. The best.

2 years ago
Reply to  SLG

Those Salt Waters from Hoy Brand seem really great, classic and comfortable looking, thank you SLG! <– for anyone who wants to take a quick peek. 🙂

2 years ago
Reply to  SLG

I love that the navy Saltwater sandals are on my third child (two boys and now a girl) and still going strong. Those and red chacos have been my best kid shoe purchases. I have both in so many sizes, and I predict that my fourth will wear them all as well!

2 years ago

When it’s warm out, I just wear Chacos all the time. They work for everything. Kim Holderness just had a video about packing for the Amazing Race, which I thought was great.

Courtney Koenig
2 years ago
Reply to  Heather

I totally agree! Chacos are the best! I have the solid colors and I can wear them with dresses or bikers. They are so comfortable! Like Disney comfortable. 😍

2 years ago

My main rule, based on blister avoidance: never take brand new shoes on vacation. If it’s too cold outside, at least wear them around the house for a few days to see if there will be fit/comfort issues.

2 years ago

You have to decide what shoes to bring based on the trip’s activities and climate you’ll be in. I always try to limit myself to 2 pairs of shoes on a trip. One pair for active wear (gym shoes or water sandals), and one pair for dressing up (flats or loafers). Then I only pack clothes that will work with the shoes. Nothing ruins a trip for me more than having too much stuff to lug around, waiting for checked bags at airports, etc. (I suppose there could be a case for a 3rd pair of shoes for some specialty activity, but even ski boots can be rented at a destination, etc.) Because you asked… To avoid overpacking start by making a packing list and deciding what you want to take. After every trip make an updated copy noting what you did or didn’t use or did or didn’t miss and the purpose/type of trip. Over time it will help you fine tune. Then when you pack refer to your packing list and lay out EVERYTHING that will be going into your suitcase(s) on your bed (including things like electronics, toiletries, etc.). Check if it’s a capsule wardrobe. Can every… Read more »

2 years ago

After 10+ years of wearing the same pair of Chacos, last Summer I traveled in the Maggie sandals from Madewell (#1 on the ‘flatform’ list). I walked many miles in them and can attest to their comfort from day 1. No blisters, no aches, and amazingly also no signs of wear despite the long walks on cobblestone streets and sandy beaches. I wish they still offered a selection of colors though! Not that I would buy them myself, because those 10-year old chacos still look like new, and I won’t be surprised if these too still look good in 2032.

2 years ago

These are really cute shoes. Thanks for sharing this amazing piece.

2 years ago

Those fisherman sandals…good grief! I haven’t really been ‘getting’ fashion for like years now but they truly confirm I’m living on another planet


2 years ago
Reply to  Christina

I hear ya! You’ve voiced my sentiment on 80% of the picks above. These are the dark days of fashion, friends. Flowy, layered small-flowered-print prairie dresses, chunky clunky dad shoes, boots, and sandals, horrendously ill-fitting 90’s jeans, acid bleached denim?! I just can’t. God help us! (atheist here, so were definitely screwed!)

2 years ago
Reply to  Molly

I am soooo happy it’s not just me. It’s such a bummer because after years of pregnancy/nursing/2nd pregnancy/more nursing/budgeting to move, etc., I finally have some disposable income to spruce up my wardrobe and the last few times I’ve gone shopping I’m kind of horrified by everything, haha!