STYLE ADVICE OF THE WEEK: Boarding School Cool

Hey there Upper East Siders. This just in: the preppy trend is back and bigger than ever. Following the advent of chic and sophisticated boyfriend blazers and oversized button-ups, next up for the casual and comfy schoolgirl look is footwear. The penny loafer was originally a staple of any workingman’s wardrobe, worn with suits as part of a business casual dress code—but no more! As Fashionistas continue to step into the menswear trend, loafers add a sleek, professional and put together look to any outfit. The feminine take on this classic shoe now comes in suede, animal prints, and sparkly sequins.

I spotted this trendsetting Fashionista, Charlotte Fassler, on the steps of Columbia looking fashion-forward and comfortable in her penny loafers. Her classically designed footwear highlights her casual yet refined look. A pair of these sleek slip-ons is the perfect complement to any casual (or formal) outfit. They are the epitome of timeless, classic styling. The low heel is great for all-day wear, and keeps Fassler walking in comfort as well as looking great as she treks across campus to class. Her chic loafer with a detailed pattern and a penny keeper on the vamp makes it a great partner for cropped pants.

Fassler’s pants are a casual crop done right. They shake up her look and draw attention to her chic footwear with a crop just above the ankles. They’re fashioned with a modern, easy fit that looks slouchy yet sophisticated. The cropped pant gives Fassler a chic silhouette, and is great for wearing during the daytime and beyond. Her peacoat is a wild take on a classic look with frisky leopard print on the cuffs and collar. This cover-up is fashionable and functional—it’s perfect for winter and adds zest to any outfit. She keeps her headwear simple with a gray wool cap that matches her loafers.

Kelly Osbourne, Katie Holmes, and Kate Bosworth were all forerunners of the loafer trend, pairing them with skinny jeans, cuffed pants, and dresses. These beautiful starlets show that these shoes are not just for the boys. Penny loafers highlight any Fashionista’s casual look and transcend the seasons with their classic design—they’re always in style. With a pair of amped-up patterned loafers, there’s no need for pennies. Let’s hear it for New England!

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