Stephanie Olivares was walking along Damen Avenue after having dinner with her boyfriend.
What do you like to wear when you go out at night?
I like wearing a piece that is structured because it always looks tailored and it can pull an outfit together very easily. I also gravitate toward skirts. You can dress them down with a comfy sweater and boots or dress them up with a cute top and pumps. You can also always mix and match creating a new outfit, versus a dress which doesn’t have much versatility.
What’s the first thing a girl should pick before dressing up?
I think you should always pick one thing that makes a statement, whether it’s the color or a piece of jewelry that inspires the rest of your outfit.
How can you make an outfit cool but at the same time dressier? Cute but also sexy?
I like contrast in an outfit. For example, if I wear a short skirt or short I’ll typically wear a long-sleeved shirt or if I wear something too sweet I usually wear chunky boots or a studded purse or jewelry. I also don’t like sticking to a certain style all the time, keeping it fresh will always work toward your advantage.
What are your favorite places to shop in Chicago?
I love shopping at Pitaya, Nordstrom Rack, Zara and Francesca’s.
—Photo and interview by Isa Giallorenzo