I Tested The Most Comfortable Sandals For 7 Days

I'm easily tricked by seemingly "comfortable" shoes; the ones that have a clunky thick sole and lots of straps (+2 points for velcro). They imply there are no pain points, but after a walk down the stairs and out the door, I start to notice the straps brush against my feet in a weird way and the uncomfortable lack of cushioning for my heel. Unfortunately by that point there's already enough wear on the soles that the shoes are rendered un-returnable. Fun. We've all witnessed the scam sandal, the one disguised as being comfortable only to betray you with a thick sole and cushy inserts that, in reality, feel like having a 40 pound weight strapped to each foot. So I set out to find the sandals that are actually worth our time.
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A little bit about my foot anatomy: I have flat feet and an extra bone on the side of my left foot so my main concerns revolve around extra support and strap placement. While every foot is different and filled with its own quirks and weaknesses, every foot undeniably wants to feel like its walking on a soft puff of clouds. There's been a steadily increasing trend of heels being left by the wayside to make way for more practical shoes. While this year has been the age of the dad sneaker, its close cousin, the chunky sandal, is just the ugly sneaker summer-ified.
With more chunky sandals on the market than ever, I decided now was the time to test the most notable ones so that your feet don't have to suffer. Click through for my week of "comfy" sandals (blister pics not included).
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Photographed by James Jiang
Monday: Skechers D'Lites

I took a tip from my mom and picked up some some throwback Skechers for day 1. In case you've blacked out during the era of Kim Kardashian acting as its main spokesperson (*ahem* Shape Ups), Skechers have always been the ultimate representation of the comfy sneaker. But the comfort can sometimes be a sacrifice for current style. Not in this case though. Someone be sure to @ Britney because Skechers are back. I loved that the sandal straps had a shiny effect and loved the way the treads looked from the bottom even more.

Bounce-back: ⭐️⭐️⭐️⭐️⭐️

Strap friction: ⭐️⭐️⭐️⭐️

Support: ⭐️⭐️⭐️⭐️⭐️

Miles Walked: 6 miles

Helmut Lang Asymmetrical Tank Top, $105, available at Shopbop; LPA Payette Sequin Draped Mini Skirt, $178, available at LPA; Darner Powder Blue Mesh Socks, $38, available at Darner; Skechers D'Lites, $55, available at Skechers.
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Photographed by James Jiang
Final Rating: ⭐️⭐️⭐️⭐️⭐️

I sprinted to the bus wearing these sandals and didn't trip once. I also made the bus (in case you were wondering). These get the 5 star rating for being superbly comfy.

Skechers D'Lites, $55, available at Skechers.
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Photographed by James Jiang
Tuesday: Marc Jacobs Sandals

I wanted to include a luxury sandal in the mix because if you're going to pay up for some fancy sandals, you should know exactly what you're getting for your money. I went with heavy, but definitely higher quality, sandal from Marc Jacobs. They're the epitome of a dad sneaker made summer friendly. In terms of comfort, the weight creates a domino effect. The pressure is tighter on the straps which made me subconsciously walk a little differently which also tired out my ankle quicker. However with rhinestones on the aglets and the sole of the shoe resembling a true sneaker, these shoes were undoubtedly the highest quality in terms of aesthetic. While the shoe wasn't the most comfortable, they did make my non-pedicured feet look great.

Bounce-back: ⭐️⭐️⭐️

Strap friction: ⭐️⭐️

Support: ⭐️⭐️⭐️

Miles Walked: 4 miles

Topshop skirt; Urban Outfitters sunglasses; Marc Jacobs Somewhere Sport Sandal, $295, available at Marc Jacobs.
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Photographed by James Jiang
Final Rating: ⭐️⭐️⭐️

Although the weight made them less comfortable, the details on the sandals themselves were so good it made up for it.

Marc Jacobs Somewhere Sport Sandal, $295, available at Marc Jacobs.
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Photographed by James Jiang
Wednesday: Dr. Martens Sandals

Dr. Martens boots are notorious for having a break-in period. Wear thick socks, carry blister band-aids, and buckle up because you're in for a ride. But the rule is that once they're broken in, you no longer have to worry about them hurting you ever again. These sandals have the famous air-cushioned sole without the painful breaking in period. The back strap was initially loose resulting in a lack of support causing some strap friction. But luckily that was fixed with the elastic laces.

Bounce-back: ⭐️⭐️⭐️⭐️⭐️

Strap friction: ⭐️⭐️⭐️

Support: ⭐️⭐️⭐️

Miles Walked: 6.4 miles

Sui Studio Cameron Navy Striped Suit, $499, available at Sui Studio; Raen Sunglasses; Dr. Martens Kristina Aunt Sally Sandals, $95, available at Dr. Martens.
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Photographed by James Jiang
Final Rating: ⭐️⭐️⭐️⭐️

Lesson learned: switch out all laces for elastic ones and the shoe will automatically move to the ebbs and flows of your foot.

Dr. Martens Kristina Aunt Sally Sandals, $95, available at Dr. Martens.
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Thursday: Fila Disruptor Sandals

I took these for a casual 7.5 mile stroll across the Williamsburg Bridge and they didn't hurt my feet at all. That's a feat of sandal technology because I definitely experienced some elevated climbs during my walk. The Fila sandals come with a lot of cushioning and the side of the straps are made from neoprene meaning there's little to no strap friction. The best way I can sum it up? I have nothing negative to say about these shoes. Also, expect mega compliments when wearing the disruptors; even in a pair of sequin shorts they totally stole the show.

Bounce-back: ⭐️⭐️⭐️⭐️⭐️

Strap friction: ⭐️⭐️⭐️⭐️⭐️

Support: ⭐️⭐️⭐️⭐️⭐️

Miles Walked: 7.5 miles

Tracksmith Relay Singlet, $65, available at Tracksmith; Anouki shorts; Fila Disruptor Sandals, $80, available at Barneys.
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Photographed by James Jiang
Final Rating: ⭐️⭐️⭐️⭐️⭐️

I would walk a thousand miles in these shoes.

Fila Disruptor Sandals, $80, available at Barneys.
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Friday: Teva Hurricane XLT 2

It wouldn't be an ugly sandal story without some good ol' Tevas. Teva makes way more comfortable shoes than these (trust me, I did a 20 mile hike in a pair once), but these fall more under its line of "fashion" sandals. The monochromatic coloring deserved 4-stars in my book and as far as fashion sandals go, they were extremely comfortable. Unfortunately as I got going, the sandal proved to feel a bit hard on the feet so no "walking on a cloud" effect was achieved.

Bounce-back: ⭐️⭐️

Strap friction: ⭐️⭐️⭐️⭐️⭐️

Support: ⭐️⭐️⭐️

Miles Walked: 5.5 miles

Topshop Roll Sleeve T-Shirt, $18, available at Topshop; Sandy Liang skirt; Bauble Bar Ariza Anklet, $36, available at Bauble Bar; Teva Hurricane XLT 2, $70, available at Teva.
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Final Rating: ⭐️⭐️⭐️⭐️

I was glad today was an easy day with the least amount of miles on these shoes They're cute, but I'll stick to my less-fashionable Tevas in the future.

Teva Hurricane XLT 2, $70, available at Teva.
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Photographed by James Jiang
Saturday: Charles and Keith Sandals

These sandals were a winner when it came to the style category. The rope detailing was beautiful and the speckled print on the front adds a whole other dimension to the shoe. Unfortunately, relative to the other shoes, this was the least comfortable. The shoe didn't have much in the way of cushioning giving it a low rating on the bounce factor scale which, in turn, affected the support.

Bounce-back: ⭐️⭐️

Strap friction: ⭐️⭐️

Support: ⭐️⭐️⭐️

Miles Walked: 6 miles

Miaou Lucy Corset, $350 $245, available at Miaou; Levi's Made and Crafted Summer Culottes, $198, available at Levi's; Charles and Keith Laced Up Rope Sandals, $59, available at Charles and Keith.
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Photographed by James Jiang
Final Rating: ⭐️⭐️⭐️

Extra points for the speckled details and lace-ups. Unfortunately, 6 miles later, I was ready to go home and give myself a much needed foot massage.

Charles and Keith Laced Up Rope Sandals, $59, available at Charles and Keith.
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Sunday: Birkenstock x Opening Ceremony Sandal

I have one rule: don't wear a backless sandal if you're planning on walking a lot. This lesson was learned the hard way when I was walking so fast that my backless sandal flew off of my foot and into the middle of the street. Luckily I chose these Birkenstocks on a Sunday where there's no a rush to get anywhere fast and it's acceptable dress up as a pillow. I found that these shoes were incredibly comfortable. The grooves make it so that your ankle isn't fatigued from trying to keep the shoe on.

Bounce-back: ⭐️⭐️⭐️⭐️⭐️

Strap friction: ⭐️⭐️⭐️⭐️⭐️

Support: ⭐️⭐️⭐️⭐️⭐️

Miles Walked: 7.5 miles

Rhode Resort Nala Dress, $335, available at Shopbop; Sleepy Jones PJ pants; Birkenstock x Opening Ceremony Glitter Arizona Sandal, $145, available at Opening Ceremony.
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Photographed by James Jiang
Final Rating: ⭐️⭐️⭐️⭐️⭐️

On mile 4 I forgot that these were even backless, a true Sunday miracle in terms of comfort and sparkle factor.

Birkenstock x Opening Ceremony Glitter Arizona Sandal, $145, available at Opening Ceremony.
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