What do you think of the street style here in Chicago from your visit so far?

I think you guys are misunderstood. I was expecting a much more conservative fashion take and I’ve been really pleasantly surprised by how fashion-forward, open-minded and embracing of the trends everyone has been. I did a different fashion show both last night and tonight and each one had a very different crowd but still everybody was really engaged in fashion. But the beauty, I gotta say! The hair, the eyelashes? I don’t know what’s going on in Chicago but I need to get with the program because I somehow missed a memo and it had something to do with big beautiful eyelashes and a curling iron!

For those trying to break into the fashion industry, what’s the key to getting your foot in the door?

I was very proactive. When I graduated from college I basically combed every masthead of every magazine and saw that Anna Wintour’s assistant was a girl from my sorority. She had been a senior when I was a freshman so I didn’t even know if she would know my name but I 411’d her number anyway and called her and she actually called me back. She had remembered me because of a hot pink dress I wore to a formal. Long story short she got me an interview and I didn’t get the first job I interviewed for there but I got the second, which was to be the assistant to the accessories director. So if this girl hadn’t have called me back I don’t know if I’d be here today.

How long did you spend trying to plan your outfit for that first interview at Vogue?

I remember going to Bendel’s and buying these really crazy earrings because I wanted to be chic but I wanted to have a statement accessory. I also remember writing out my answers to every possible interview question and doing a mock rehearsal with my mother in Starbucks. I had to interview with Anna Wintour so my mom played the role of Anna. And I got the job! So I worked my way up at Vogue to assistant accessories editor and that was really amazing, they gave me a lot of responsibility right out of the gate. I left Vogue when I got an opportunity to go to InStyle magazine as the associate accessories editor which ended up being the best training for what I do now at Bloomingdale’s. 

So your life was kind of like the real-life version of “The Devil Wears Prada”.

Having worked there it was really crazy when that movie came out. I think, yes, everything is an exaggeration but every art form that is based on reality has some truth to it. I have to say though, Ms. Wintour was nothing but wonderful to me. She interviewed me, she hired me and I have nothing but pleasant things to say about her.

How did you make the jump from magazines to a department store?

One day I met this woman and she complimented something I had on and then I complimented something she had on. We got to talking and she asked what I did and when I asked her the same she said she was the fashion accessories director at Bloomingdale’s. I said, “What does that mean?” and when she told I was like,”I want your job!” She said, “Well, I’m not going anywhere right now,” but I gave her my card in case she ever left. A year later I got a phone call and it was her. She said, “Brooke, I don’t know if you remember me but I’m that girl that you met. I’m leaving and you would be perfect for the job,” so I came in and now I’ve been here for six years.

Stepping into a role with so much responsibility and influence at the age of 27, did you feel prepared?

To be the fashion director of a brand with 33 stores is a lot. I doubted myself tremendously my first year. There are always challenges, there are always growth spurts, there are always days you doubt yourself but I’ve always held myself to the, “I can do anything for a year,” mantra. That usually gets me through everything and I’m so glad because I look back now and think, “God, I was such a different person then. I’m so glad I stuck it out.”

What is the thought process behind the shoe selection for the Chicago Bloomie’s shopper?

First and foremost I always bring my own sensibility to the job but it’s not about me, it’s about the customer. I’m constantly trying to understand who our girl is, what she wants and it differs by store so we really try to tailor what we do to the area. I’ve learned a lot on this trip to Chicago and that will really impact some of the future decisions I make. I think you guys want fashion that’s cutting edge but I think there’s a need for a real balance between that and also having comfort. There are a lot of working girls here so I think you guys need variety. I think a lot of gut instinct goes into what I do and that just comes from years of looking at accessories.

What trends will we be seeing soon?

Trends come in really interesting cycles. For example right now what’s happening is we’re in a dress cycle where pumps are really important. Then all of a sudden you see something like sneakers come in and smoking shoes and that always indicates the beginning of a casual trend so it will be really interesting to see the pendulum swing. When we’re in cycles we tend to be in them for a few years.

Do you have a look that you wish you never took part of?

I don’t ever regret anything happening but I will say for the first two to three years of my job we were so into aggressive platforms and they just look so wrong to me right now! I don’t know if it’s the impact of Kate Middleton but I really feel she made the more ladylike looks in again. I think designers like Céline and Raf Simons of Christian Dior—who came from Jil Sander, a very minimalistic and more streamlined designer—make that chic pointed-toe single-sole pump look so right on the money. It’s amazing how that happens because I remember when the platform was big, now it just makes someone look so wrong!

What is your favorite part of working in the New York City fashion scene?

What I love about New York is that the look changes by neighborhood. You can go to the East Village and that’s where a lot of times you’ll see the trends first. I love seeing things in the street that then happen on the runway, the early adopters that will start wearing the short skirt that’s long in the back with the cool graphic tee or the anorak. Sometimes I don’t know what comes first, the street style or the runway and sometimes I think it’s the street. Sometimes I’d rather look at what people are wearing in the audience of fashion week than what they’re wearing on the runway. I think that it’s the fusion of both of those things that confirms for me what the trends are a lot of the times. Because if it’s on the runway and then it gets adopted in the street then that means it’s viable and the customer will buy it. 

What are some of the best restaurants for us to check out when we’re in town?

Balthazar gets talked about a lot but it’s still my favorite place. I love it, it looks like a French brasserie and it’s still the place where I want to go on my birthday. I’ve never ordered anything that I’m not excited about there. I live in the Upper East Side and near my house I love Sushi of Gari. Get the omakase and they’ll bring you whatever the chef catches that day. My favorite Italian restaurant happens to be in my neighborhood but I’m scared to tell anyone because I don’t want to not be able to get a reservation! It’s called Antonucci. It’s on East 81st Street and it’s my little haven of delicious homemade pasta. I love food so you’re asking somebody that has so many answers!

If you could have a drink with anyone, who would it be?

Besides Bradley Cooper? I think Shakespeare! 

ALINA TSVOR PHOTOGRAPHY