What to Wear at a Casual Office: 5 Work-to-Happy-Hour Outfit Ideas, From Newcomer Brand 424 Fifth

A patent bomber jacket and tweed pencil skirt: Mix materials like a relaxed T-shirt and tweed pencil skirt for a casual-Friday outfit. "When heading out of the office, throw the patent bomber over your shoulders for a nighttime-cool finish," says Holman-Rao.

An oversize vest, floral camisole, slouchy pants, and black pumps: "After work, just remove the vest and add an armful of a bracelets or a statement necklace for a sexy evening look," she says.

A striped jacket and full calf-length skirt: Yes, that's a crop top you see, but "zipped up, this jacket and skirt combo is perfect for capturing the season's ladylike trend in the office," says Holman-Rao. "After hours, this outer layer works best either unzipped or draped over your shoulders for a more bare evening look."