Tour Trunk Club's Stellar Office Space

It is, perhaps, behind your boyfriend's urge to put on a tie — or the reason why you can't keep your eyes off of the sharp-dressed man across the room. But, Trunk Club, the super-cool, technology-powered online (and on-site) shopping service, sure is responsible for making men nationwide look their absolute best. Of course, it takes an equally fashionable crowd to raise such a sartorial bar, so we headed to the rad Trunk Club H.Q. in River North to scope out its stylish staff for ourselves.
Just one look at VP of merchandising Jason Smith or the top-tier stylists, and you'll quickly recognize that there's no such thing as a casual Friday at this office. But with a sprawling bar and rooftop deck, stuffy work environment this is not. Trust, once you see these snaps, you're going to want to be a part of the club, stat.
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Photographed by Lucy Hewett.
How long has Trunk Club been in business and what's its core philosophy?
"Trunk Club is the first and only technology-powered shopping service that makes looking good effortless and getting dressed a little less foolproof," says CEO Brian Spaly. "It was originally founded in 2008 in Bend, Oregon, as an innovative new way for men to work with personal shoppers via Skype video sessions. The business was purchased by Anthos Capital and relocated to Chicago in December 2009 under my leadership."
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Photographed by Lucy Hewett.
Alex Palmer: Stylist

Tell us a little bit about your role.
"I wear many hats as a stylist! I spend the majority of my day picking out outfits and clothes to send my clients and taking in-person styling/shopping appointments with my guys who are in Chicago. I am constantly adding to my book of business, so I also spend a lot of time emailing and calling my clients or reaching out to prospective guys."

Taylor Prokos: Senior Stylist

What are a few pieces clothing or accessories that every man should own?
"A quality pair of denim jeans, a versatile pair of brown shoes, a navy sport coat, and a thin V-neck sweater."

Lauren Jarrett: Member Experience, Style Consultant

What's your favorite in-office tradition?
"I enjoy our candy drawer — gummy bears and peanut butter cups are my favorites. Every day is something new in our office, so laughter is always heard and music is always playing. That in and of itself makes Trunk Club so special to me. Everyone is a little weird in his or her own way, but that's what makes this business run."

Alex is wearing a Zara blouse, Seven shorts, Fiorentini & Baker boots, Dana Rebecca Designs jewelry, and a Concord watch. Taylor is wearing J Brand jeans, a Life After Denim sweater, Clae shoes, and a Timex watch. Lauren is wearing Levis jeans, a Banana Republic shirt, Steve Madden shoes, and vintage, Henri Bendel, and Michael Kors jewelry.
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Photographed by Lucy Hewett.
Details of Jarrett's killer stems and accessories.
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Photographed by Lucy Hewett.
Joe Jarvis: Lead Writer

Tell us a little bit about your role.
"My team creates written content for our blog, emails, the new Trunk Club iPhone app, and more.

Do you keep anything cool at your desk that helps you get through the day?
"A Lemon Ball baseball, which I use as a squeeze-toy to relieve stress. When that doesn't work, I just throw it at people. For inspiration, I've got a couple of issues of FANTASTIC MAN, the best men's fashion publication I've ever seen."

Joe is wearing an Eton shirt, United jeans, and Oak Street Bootmakers shoes.
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Photographed by Lucy Hewett.
Despite the modern-day technology behind Trunk Club, the office vibe is old-school cool.
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Photographed by Lucy Hewett.
What looks like a friend's hip pad is actually a sweet meeting room. Boardroom, what?
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Photographed by Lucy Hewett.
Lauren Regole: Merchandise Planner

Tell us a little bit about your role.
"I'm on the close-knit merchandising team here at TC. We are in charge of analyzing the past/current performance of our clothes. We use that analysis to forecast and buy clothing for the future and implementing strategies to impact those sales. I spend a ton of time in Excel and an equal amount of time around the product and our vendors, so it's a good balance of desk and non-desk time."

What is your idea of a sharp-dressed man?
"I used to be a sucker for a preppy guy in chinos, a colorful plaid button-down, and boat shoes. But as I've gotten older, I've learned to appreciate the power of a great fitting suit — preferably paired with an open-collared shirt and brogues."

Lauren is wearing an O by Organic skirt, Madewell shirt, Pour La Victoire shoes, and J.Crew earrings.
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Photographed by Lucy Hewett.
Raynard C. Woods: Operations Army

Tell us a little bit about your role.
"As a member of Trunk Club's operations army, my main responsibilities include fulfilling trunk requests, processing orders, and shipping outgoing orders."

What are a few pieces clothing or accessories that every man should own?
"Colorful pants ARE A MUST. I'd say they are the second biggest statement piece in your closet next to a great blazer. Every guy should have a pair of pants that give an extra pop of color while telling everyone, 'I'm here to have a great time.'"

Raynard is wearing an Alternative Apparel shirt, Vince pants, and Zara shoes.
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Photographed by Lucy Hewett.
The entire office boasts floor-to-ceiling windows with killer views of the River North 'hood.
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Photographed by Lucy Hewett.
The building is over 100 years old, so the natural bones of the space are unbeatable" says Smith. "Even so, trying to stay true to the natural environment is not easy, so we are lucky to have brands like Billy Reid, John Varvatos, and Ghurka contribute lounges with distinct personalities. We have also been really fortunate to have relationships with companies like Restoration Hardware and Kohler — both have been wonderful to us."
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Photographed by Lucy Hewett.
The tabletops are piled with aspirational lookbooks and magazines.
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Photographed by Lucy Hewett.
Jason Smith: VP of Merchandising

Tell us a little bit about your role.
"This doesn't feel like work because we are having way too much fun building this company. But to get specific, it's honestly a little bit of everything these days. My team selects and manages all of the inventory and product that comes into Trunk Club. I work very closely with the sales team from a cultural and brand standpoint. I spend a lot of time with the creative team working on stories, images, and ideas that we think will be interesting and helpful to our clients. As much as I can, I still find time to sell our product and work with our clients."

Do you keep anything cool at your desk that helps you get through the day?
"I keep a bottle of Veuve Clicquot Rose at my desk at all times. You never know when you are going to need to pop open a bottle of Champagne and start celebrating."

Jason is wearing an Eton Green Label shirt, J Brand jeans, L.B.M. 1911 jacket, Oak Street Bootmakers exclusively for Trunk Club shoes, Rolex watch, and Prada glasses.
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Photographed by Lucy Hewett.
Details of Smith's super-cool double-breasted jacket.
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Photographed by Lucy Hewett.
Just another day at the office.
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Photographed by Lucy Hewett.
Part of the incredible inventory scattered throughout Trunk Club.
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Photographed by Lucy Hewett.
Coabi Shapiro: Sales Director

What's your favorite in-office tradition? "
For the past two years, the sales team has celebrated record-breaking months with a trip to the cubs game, followed by a party at a bar in Wrigleyville. Both times, the day included a team wide sing-along to Whitney Houston's 'How Will I Know,' which just so happens to be my favorite karaoke song!"

Nicole Gable: Director of Sales

Do you keep anything cool at your desk that helps you get through the day?
"A survival-kit box, filled with vitamins, Andes chocolates, nail-polish remover, a lint roller, toothbrush, eye cream...essentially a portable Walgreens."

Elle Bruno: Sales Director

What is your idea of a sharp-dressed man?
"A man that is willing to step outside the box with his wardrobe and wears his clothes with confidence! A perfect date-night outfit would be dark slim denim, a madras plaid shirt (tucked in), an unconstructed blazer, and a playful pair of driving loafers or boots."

Coabi is wearing an Equipment shirt, Joie jacket, Patterson J. Kincaid skirt, Zara shoes, and Cartier and Hermes jewelry. Nicole is wearing a vintage skirt, Lamb shoes, custom-made belt, and Cartier and H&M jewelry. Elle is wearing a Mink Pink dress, Elizabeth & James jacket, Barbara Bui shoes, and Hermes bracelet.
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Photographed by Lucy Hewett.
Shapiro sporting the perfect nude summer sandal from Zara.
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Photographed by Lucy Hewett.
And we couldn't get enough of her skirt either! A perfect transitional piece as we head into fall.
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Photographed by Lucy Hewett.
The cool Trunk Club HQ was designed by local interior designer Kara Mann. Looks like your boss might have a phone call to make...
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