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1. Old Navy The price speaks for itself. Any flip flop for $2.50 is not for the faint of feet. Flimsy plastic eschews the crucial support needed to ensure feet stay in working order and don’t get bent out of shape. Tip: always invest in quality sandals and casual kicks only from trusted footwear brands – your feet will thank you, and your friends will compliment you. Source: Pinterest #flipflop #freeyourtoes #heel #oldnavy #footwear #flimsy

Bonus Entry: Worst Heeled Lifetime Achievement Award While the “Scary Beautiful” shoe debuted in 2012, it makes this list for the Lifetime Achievement Award. They were created by Cape Town-based designer Leanie van der Vyver for a college graduation project, a hybrid shoe/art installment intended as a commentary on the current fashion industry standards. We do appreciate these shoes for making us think…about immediately getting into our most comfortable pair of flip flops.

Bonus Entry: Celebrity Worst Heeled Moment We interrupt this countdown to bring you a 2013 celebrity worst heeled moment. The usually elegant Julianne Moore unfortunately got it toe-tally wrong at the Cannes Film Festival Opening Ceremony when her pinky toe runneth over. Or maybe she’s trying to start a reverse flip flop trend? Source: Oddities123.com #flipflop #heel #freeyourtoes #juliannemoore #celebrity

2. Winde Rienstra We give our Euro neighbors credit for cutting edge fashion sense, but we draw the line at shoes which appear to be cut from trees. These lookers (actually from cardboard) were created as part of the Spring/Summer 2014 runway collection by imaginative Amsterdam designer Winde Rienstra. Although we can’t get behind them, Ms. Rienstra gets props for fashioning footwear from recycled materials. Now that part, we love. Source: TrendHunter #flipflop #heel #freeyourtoes

3. Maison Martin Magiella Metallic two tones. Cloven-like toes. Plastic heel stumps. What could possibly go wrong? You’re looking at it. The hot mess “Brushed Effect Tabi Boots” is sort of a boot-meets-sandal psychedelic love child, and retails for $873. But can we gush over that luscious green leather for a moment? If it had only stopped there. Source: shopbop.com #flipflop #heel #freeyourtoes

4. Prada How do we not love thee? Let us count the ways. 1. Leather sandal socks. 2. Double decker platforms. These Geisha-inspired shoes stomped the runway back in 2012 for Prada’s Spring/Summer 2013 collection. We’re all for sandals, but somehow this look misses both the comfort and style marks. Source: Pinterest #flipflop #heel #freeyourtoes

5. United Nude Number five is a two for one special – the “Eamz Pump” (top, $290) and the “Step Mobius Pump” (bottom, $325), both by architecturally-driven brand United Nude. The Mobius looks like it ran away with the display rack, while the Eamz resembles a door stop. Actually, shhhh…we’re secretly in love with both, just don’t tell our flip flops. Source: SHOPBOP #flipflop #heel #freeyourtoes

6. Jeffrey Campbell It’s a party on heels! The “Icy” shoe by Jeffrey Campbell is filled with loose confetti and retails for $255. Props for creativity. Negative props for setting people up to topple to their plastic doom. Source: solestruck.com #flipflop #heel #freeyourtoes

7. Sergio Toro These shoes speak for themselves. Or for Batwoman. Made to order by avant garde NYC designer Sergio Toro, the show stopping “Manta” goes for a cool $3,500. But what’s the price of beauty when your shoes are certifiably bad a**? Source: Pinterest #flipflop #freeyourtoes #heel

8. Anastasia Radevich This $1,350 furry contraption by Canadian designer Anastasia Radevich makes a statement. We’re just not sure what it is. And while the heel looks like it could pop open a bottle in a pinch, we prefer to keep our feet practically on the ground with REEF’s famous built-in-bottle-opener flip flops.Source: Pinterest #flipflop #heel #freeyourtoes

9. Dolce & Gabbana You know those times when you’re in a pinch for a mini bird cage? This Dolce & Gabbana creation comes to the rescue. Spotted at the designer’s Fall-Winter 2013 runway show in Milan, they will have your feet chirping notes of sorrow in no time. On the plus side, these are perfect for all those fairy-themed cocktail parties you’re invited to. Source: Pinterest #flipflop #heel #freeyourtoes

10. Privileged Shoes We spotted the gravity-defying “missing heel” trend everywhere this year - as a rule, we don’t have any shoe’s back that is destined to hurt ours. However, it was this $175 gem from Privileged Shoes that stopped our disco ball in its tracks. While it may be painful to look at, aesthetic points go to the jelly-inspired baubles for giving us a brief Candy Crush fix. #flipflop #heel #freeyourtoes