It’s hard to call Shannon Sangster just one thing. Even his name has four parts to it: Shannon Jamar Eaton Sangster. And professionally, he’s a designer, DJ, poet, and brand ambassador. Sangster initially dipped his toes in the design world a few years back when he launched a line of ties called Fresh & Proper, and has since begun working with adidas to get the word out about the performance tech in the brand’s sneakers. At night he’s at Chicago’s Sub 51 or Studio Paris Nightclub blasting hip-hop, house music, and even Katy Perry for the late-night crowd. So, if there is one word to describe Sangster, it might just have to be tastemaker. Either way, he's got swagger, no doubt. We caught up with the Windy City slicker to talk about his favorite hot spots, cold-weather trends, and his grooming game.

Interview by Kristen Dold (@KristenDold)
Photography by Nolis Anderson (@Nolis)

What’s a typical weekend in Chicago like for you?
I might be up in Wilmette at the Baha’i Temple just hanging out for a little bit, or I might be downtown at Soho House catching lunch and doing a little work. Some of my favorite stores to shop at are Apartment Number 9 and RSVP Gallery. There are so many good eats because Chicago is so multicultural, from little restaurants like Lula Café to great Mexican food to high level, five-star cuisine like Avec. You get a little bit of everything.

You move around a lot—where do you get your inspiration from?
For a true creative, I think life can be inspiring. I’m a longtime writer and poet, so without sounding too cliché, you can find poetry in the everyday. It can be the simplest thing, like waking up next to my girlfriend in the morning or being out at night and hearing the right song or being with my friends while one of us is DJing. That’s the cool part about living in the city—you can find inspiration everywhere.

Photo by Nolis Anderson

What’s the first thing you do in the morning when you wake up?
I hop in the shower, brush my teeth, and get ready to shave. I’ll put on a pre-shave and shaving cream, then shave, and follow with an aftershave. I’ve started a pretty extensive washing regimen, too. I’ll use face wash in the morning and evening and exfoliate three times a week. It’s funny—most guys don’t know to do this stuff but you notice the benefits immediately.

Do you have any other grooming habits?
I get my hair cut every week. I actually have a standing appointment with my barber Andrew Henderson. He cuts at his own private shop and does a lot of Bears and Bulls players. We’ve become good friends. I’ve been going to a barbershop my whole life, so I can’t stand men’s salons.

What does living sharp mean to you?
I think it’s being both fresh and proper. Having the ability to clean-shave and put on a tie and nice suit jacket, but also holding on to that street essence, some of that nonchalance. Combining those two worlds seamlessly is what being sharp means to me. You have a taste level, and an idea of who you are, and putting those worlds together in a way that’s fitting for you.

Photo by Nolis Anderson

Is there something unique about fashion in Chicago that sets it apart from other cities?
Chicago fashion is just real because we’ve got to make it through the winter. You have to have the ability to layer an outfit or be a little more dimensional. There’s a multitude of different ways to express yourself due to the nature of the weather here. Fall is one of my favorite times in Chicago because we typically get these extended summers until October, so you really have to layer up or down.

Style is clearly a big part of your day to day, so how has your overall image contributed to your career success?
The way you express yourself and get dressed everyday is all about a specific mood, and if you look the part and you dress for success, you have that feeling. I’ve always dressed for myself, even when working in retail. While at Marc Jacobs, I’d take whatever Marc was doing at the time and put my own twist on it. Being unique has defined me outside of other people.

Photo by Nolis Anderson

What trends are you into right now?
I’m really into the longer drape. A lot of people have been doing elongated tees. They’ve sort of been taking that Rick Owens format and turning it into their own expression. I like that silhouette because it’s very streetwear—the bagginess stems from hip-hop—but it’s tailored in a way that works. It looks really cool if you wear it right and have the right proportions.

How do you define success? Do you feel like you’ve reached it?
I’ve had blips of success, but as I’ve gotten older, success, to me, is really defined in the freedom to do what you want to do—not so much an end goal, but a process or journey. Not having to be constrained to do things I don’t want to do, or have to be somewhere or have to go somewhere. To seamlessly integrate life and work is the goal. It’s a very millennial thing; 2015 kids aren’t trying to go into an office and work for someone in this very structured space. If I have an iPhone and a computer I can work from wherever I want. That’s the future to me. That’s freedom.

Photo by Nolis Anderson