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Home Entertainment

13 Truly Comfortable Charleston-Style Sandals to Look Old Money-Rich

by DigestWire member
July 11, 2025
in Entertainment
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13 Truly Comfortable Charleston-Style Sandals to Look Old Money-Rich
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Everyone dreams of wearing truly comfortable sandals — shoes that fit properly, provide support and essentially feel like sneakers. Some fit the description yet fail in the style department, making them a no-go for fashionistas like Us. If you’re looking for comfy sandals that check every box while elevating your outfit, browse these Charleston-inspired picks.

The sandals you’ll find below are all versatile, expensive-looking and secretly supportive, which is why they’re perfect for luxury-loving comfort connoisseurs. Options include classic flat sandals, platform wedges and cushioned slides from brands like Dr. Scholl’s, Vionic, Reef and Dream Pairs, starting at just $17. So if you’re ready to upgrade your wardrobe, check out these 13 bestsellers that are hiding on Amazon and Zappos before they sell out.

13 Supportive Charleston-Style Sandals to Look Old Money-Rich

1. Our Favorite: Have you ever seen such chic sandals? These strappy wonders have a plush microfiber footbed, anatomical cushioning and an ultra-slim wedge.

2. Dream Style: Everything about these flat sandals are classy — from the cork footbed to the smooth (faux) leather straps.

3. Narrow Feet: Shoppers with narrow, regular and wide feet can’t stop buying these timeless Naot sandals that have a secret Velcro closure.

4. Amazon’s Choice: Equally supportive and stylish, these dramatic open-toe shoes have a shiny oversized buckle that screams ‘rich mom.’

19 Comfy, Rich-Looking Sandals on Sale for Amazon Prime Day

5. Bestseller Alert: Don’t just take our word for it: These strappy cork sandals have tons of nearly perfect reviews! We adore the snakeskin look.

6. Extra Cushioning: If you really want sandals that feel like sneakers, these sporty kicks have your name on them. The cushioned sole absorbs shock and gives every step a boost!

7. Raffia and Leather: You’ll wear these yacht-ready T-strap sandals everywhere, whether running errands, logging miles or meeting the girls for brunch.

8. Sparkly Disposition: Turn heads effortlessly in these rhinestone-embellished sandals that have a mini wedge for extra height.

9. Worth It: These designer-looking sandals will transport you to a coastal Italian villa. They even hug your arches for a custom feel.

10. Dressed Up: Weddings? Check. Work events? Check. Fancy dinners? Check. These platform wedges are the ‘everything’ sandals you’ve been hoping for!

11. Braided Beauty: We’re a little (a lot) obsessed with these braided slip-on sandals that provide extra alignment support. Nobody would ever know they’re comfortable.

12. Zen Choice: Want to feel like you’re walking on yoga mats? These cushiony slides have an orthotic footbed and a wear-everywhere style.

13. Quiet Luxury: Shiny and minimal, these slip-on walking sandals beg to be worn with maxi dresses this summer.

15 Comfy Shirt Dresses to Look Effortlessly Polished — All Under $30

Us Weekly has affiliate partnerships. We receive compensation when you click on a link and make a purchase. Learn more!

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