From Coffee to Cocktails: Mastering the Day-to-Night Style Shift

Posted by Chelsea Lankford on Aug 25th 2025

Back in my days of buzzing around the Minneapolis skyway system as a young professional, the day-to-night transition was essential. I worked in finance by day and fashion by night, and carrying a look from coffee to cocktails became like a third full-time job. While I learned a swipe of lipstick can take you far, it takes a bit of planning ahead to effortlessly transition an outfit from daytime to night hours. Besides a mini-to-go bag with hair products or makeup or cologne, here are a few clothing or accessory swaps that make a big impact when switching up your look for nighttime wear.

Person walking along a brick wall covered with green ivy, wearing a patterned jacket over a white top, blue jeans, tan shoes, and carrying a brown handbag

Earrings are the first thing I change when it comes to accessorizing an evening look. Every day is either a pearl stud or a small gold hoop, and swapping these daintier pieces out for colorful drop earrings or a dramatic pair of studs is instantly eye-catching. Outwear is another key element. Most of us have a go-to, all-weather jacket that carries us through every day. For an evening event, take along a structured blazer or leather jacket to elevate a casual daytime dress or blouse and pants.

Person sitting on a city bench wearing a black wide-brim hat, black studded leather jacket, and striped top, with traffic and tall office buildings in the background.

We’re still in an era of dressing more casually for the office, but men have the capacity to bring a little more personal flair to their workwear for after-hours just as much as the ladies do. If you’re a sneaker guy, put a pair of Chelsea boots in your car with a smart jacket, like a sleek bomber or tailored chore jacket, that will instantly take a button-up and slacks from casual office day to an evening soirée.

Close-up of a person wearing a white lace long-sleeve blouse paired with dark blue jeans, holding a small leopard-print bucket bag with a gold chain strap

One of my go-to hacks was to use a clutch purse as my wallet and keep that inside my work tote, so I would always be ready with more dressed-up bags, sparkles or leopard print or studs— when the occasion called for it. Get creative with what switches your mood from day to night: is it a color story that you update? Layering different textures or finishes? Once you’ve found your formula of comfort and style, you’ll be ready for anything when five o’clock rolls around.

Blog By: Chelsea Lankford | @truelane