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To successfully transition from work to happy hour, fashion consultant Reginald Ferguson recommends choosing versatile workwear that can be easily dressed up or down. For a seamless transition, choose items like midi dresses, loafers, polo shirts, and chunky heels. Plan ahead and dress comfortably, and be prepared to shed layers and add accessories to switch from work attire to a more casual look. Ferguson also advises against ripped jeans, crop tops, and graphic tees, suggesting that torn jeans are only acceptable if you work in a club.

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