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Pros Elegant Excellent color options Pairs with denim perfectly Cons Tough break-in period Our Gear & Commerce Editor has had these OG penny loafers since 2020 and can now firmly stand behind them as the perfect shoe for dressing up even the most casual attire

Burgundy Scarf Neck Dress With Slingback Heels A burgundy dress with an attached scarf at the neckline channels vintage screen-star energy in the most sophisticated way

During her second pregnancy in August 2019, Hathaway wore a hot pink dress with rib cutouts

And while the military-inspired Buck Mason pair had a lot of nice period details, the button fly was impossibly hard to do up