Let’s be honest—most “comfortable” summer shoes fall into one of two categories: orthopedic chic (read: not chic) or glorified house slippers. But you deserve better than shoes that whisper, “I gave up”. 

Good news: Comfort and style can coexist—and I’m sharing the summer shoes that prove it. These styles deliver all-day wearability without sacrificing style. No awkward silhouettes. No orthopedic vibes. Just polished, put-together options you’ll actually want to show off.

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(Note: clicking on the following products will take you right to them! If you choose to purchase something, WWTNT may get a commission at no additional fee to you. But don’t worry, being a seasoned stylist, I only choose products I truly value and think will successfully meet your needs.)

 

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The Elevated Slide

Think: sleek leather, minimalist hardware, and walkable soles that still feel luxurious.
Look for: soft padded footbeds, wide straps for support, and slight to moderate platforms for style without strain.
Erin’s Pick: Polished low heel slides that peek out from beneath wide leg pants and platform slides to go with dresses and skirts.

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The Low-Heel That Doesn’t Fall Flat

A tiny heel goes a long way in sophistication—and doesn’t sacrifice comfort if you choose wisely.
Look for: block heels, suede or soft leather uppers, and a snug fit that stays put.
Erin’s Pick: Animal print kitten-heels with architectural lines and anything by Vince.

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The Stylish Sneaker

Not your gym shoes. Think crisp, clean lines and subtle details that elevate even your simplest outfit.
Look for: neutral tones, soft leather, and styles that pair just as easily with dresses as they do with denim.
Erin’s Pick: Veja, Vince, or Linea Paolo for sleek, grown-up sneakers that still feel fresh.

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The Chic Sport Sandal

Once reserved for river rafting—now reimagined for the fashion-forward.
Look for: mixed materials (like leather + neoprene), tonal color palettes, and molded footbeds.
Erin’s Pick: Anything with neoprene or elastic straps for a form fit – think of these as the cooler cousin to Tevas—without the camping connotations.

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The Polished Espadrille

A classic that’s come a long way. Today’s espadrilles are slimmer, more flattering, and way more versatile.
Look for: ankle ties or straps, structured slim shapes and try a variety of wedge heights to find your comfort zone.
Erin’s Pick: Cole Haan’s espadrille – there’s a reason it’s called “Cloudfeel”.

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The Comfortable High Heel (Yes, It Exists)

You don’t have to retire heels—you just have to be strategic. The right high heel can elongate your legs and comfortably carry you through sundown.
Look for: heels under 3 1/2 inches, block or wedge heels for stability, and cushioned footbeds. Styles with ankle straps or slingbacks add extra security (and style points).
Erin’s Pick: Architectural shoes with a sculptural twist—think more modern art museum than corporate dress code.

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Hot Tip From a Stylist:
Always check for hidden arch support, padded insoles, and grippy outsoles—comfort isn’t about sacrificing style, it’s about making smart choices in disguise.

The Bottom Line:
You don’t have to pick between looking good and feeling good. With the right summer shoes, you can do both—and leave the “old lady” stereotypes in the dust. For more comfortable shoes choices, visit my personally curated Nordstrom shop.