Comfortably Sporty Shoes You'll Live in All Summer Long

Summer travel calls for at least one pair of casual, sporty shoes to serve as your companion while you run around town or the park with your kids. I recently went on an epic hunt for shoes that are comfortable and classic all at once—and boy, did I have my work cut out for me. Staying on your feet all day is no problem in these comfy kicks.

Check out my favorite pairs the slideshow.

More Summer Fashion:

Comfortably Chic Shoes You'll Live in All Summer Long

Sperry Seacoast Weathered Sneakers

I have a soft spot for sporty shoes like these Sperry Seacoast Weathered Sneakers ($85). They’re so relaxed and easy to wear---just slip them on and go! They channel a carefree spirit I associate with my childhood summers. They have a great worn-in look, as if they’ve been around the block a couple of times---and in this case, that’s a totally good thing.
FitFlop Cha Cha Flip Flops

Flip flops are notoriously comfortable, but they’re also seriously bland. Many brands try, but I don’t want to walk around with bedazzled flips or wedge styles that look like I robbed the Spice Girls in 1997. Then a pair of FitFlop Cha Cha Flip Flops ($69.90) caught my eye and---bam!---all my flip woes were solved. These offer FitFlop’s trademarked Microwobbleboard technology, a triple-layered platform that absorbs shock with every step. A little fringe gives it a playful look without venturing into schoolyard territory. Cute and comfortable---you can’t top that.
Sanuk Yoga Sling Sandals

If you buy only one more item this summer, make it a pair of Sanuk Yoga Sling Sandals ($36). Inspired by the laid-back yoga lifestyle, the shoes are impressively constructed; the Sling footbed is made from an actual yoga mat, a spongy outsole, and the stretchiest fabric imaginable. These may be the comfiest shoes I have ever owned, and they are available in countless solids and prints. Wear them with a dress, a pair of shorts…you name it.
NoSoX Prima Flats

Taking its cue from schoolgirl style, NoSoX Prima Flats ($70) are as comfortable as they are sweetly chic. Think of it as a Mary Jane with a twist---the criss-cross straps keep feet from slipping out, and every step is lighter than the last thanks to the soft insole and malleable Eleprint outsole.
Tieks by Gavrieli Flats

Whether you’re searching for the perfect travel shoe or a cute shoe to see you through the entire season, you can’t go wrong with Tieks by Gavrieli Flats ($175). Made with smooth Italian leather, non-skid soles, and a cushioned Achilles support (ahhh!), they are far and away some of the most comfortable flats I’ve worn. And while they don’t come cheap, they’ll pay for themselves in no time at all---that’s how much you’ll love these.
Kork-Ease Gracen Sandals

You don’t have to eschew heels completely in your search for blissful comfort. Kork-Ease Gracen Sandals ($99.90) look like they’d wear you out in less than a few steps, but don’t let appearances deceive you. With its padded insole, supple leather, and sturdy design, it’s one of the most walkable wedges I’ve worn. Bonus points for the way they elongate legs.
Keds Damsel Wedges

Another heeled option that is to-die-for cute is a pair of Keds Damsel Wedges ($29.95). I love the nautical influence and the easy slip-on style. With a denim skirt and a simple white tee, these are quite possibly the most effortless shoes of the season.
Nike Roshe One Slip Sneakers

Nestle your feet in the supportive cocoon of these Nike Roshe One Slip Sneakers ($58.49). Available in several colors, they fit active lifestyles much like a traditional sneaker---without the bulk of your go-to lace ups. From their breathable fabric to their fun design, they’re perfect for errand runs, long walks, and everything in between.