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These Classic, Fan-Favorite Shoes Are Now Comfier Than Ever

These Classic Shoes You Know and Love Just Received an Innovative, Comfort-First Upgrade

Certain shoes never go out of style. Teaming up with Cole Haan and Zappos, we're sharing two timeless styles that are now comfier than ever.

Regardless of your taste, how big your closet is, or even your age, chances are, you own at least one pair of pumps and one pair of loafers. Their versatility, timelessness, and sheer sophistication solidified these two shoe styles as must haves decades ago. And today, they're just as relevant as ever. But one thing that has changed since pumps and loafers first stepped onto the fashion scene? Technology!

Thanks to Cole Haan's Modern Classics collection, your favorite shoes have been updated with an innovative dose of comfort and durability. The collection features heritage silhouettes — like pumps and loafers — upgraded with the cushioning, flexibility, and traction technology of the future.

These shoes are all about maintaining a dressy, traditional look with the 24/7 comfort we all need. Because when it comes down to it, comfortable shoes most definitely count as an act of self-care!

Ahead, see how we're mixing modernism with both comfort and tradition by styling our favorite pairs for fall.

The Wear-With-Everything Tan Loafer

The Modern Classics loafer has added flexibility to the forepart of the shoe that typical dress loafers don't have. It also has extra toe-to-heel cushioning and a sturdy rubber outsole to keep you from slipping. All that while maintaining a classic, elevated look.

Style this pair for every day by combining it with straight-leg jeans and a cropped, roomy sweater. The beauty of loafers is that they can be dressed up or down. Gold statement earrings and a polished bag finish it off with a touch of glam, while a simple swap of minimal studs and a canvas tote would give off a subtle, casual vibe.

The Ever-Chic Black Pump

A staple in any collection, the Modern Classics pump features a sleek, pointed-toe silhouette with a square topline. Endlessly versatile, this heel is also comfortable enough for all-day wear due to its leather upper lining, cushioned footbed, and wrapped block heel.

Give this black pair a fresh 2020 spin by styling it with crisp Bermuda dress shorts, a strapless bandeau top, and a plaid boyfriend blazer. Flattering and surprisingly easy to pull off, all you need is a simple black bag to tie it all together.

The Statement-Making Printed Loafer

Just as necessary as a solid pair, printed loafers add a fun edge to any look. Think of this python print as a neutral, and try pairing it with an A-line miniskirt for a quintessential fall feel. This puff-sleeve sweater is the perfect mix of trendy and sophisticated, while playful accessories like round sunglasses and colorful hair clips finish off the outfit with a cheerful pop of character.

The Eye-Popping Red Suede Pump

Never underestimate the power of a fiery pair of heels. Not only are these red suede ones vibrant and alluring, but they're also sensible and comfy. Let them steal the show in a simple and chic monochromatic look. All black with a pop of red never fails! The only accessories you'll need are gold hoops and a bold lip.

Shop these Classic Shoes