UPDATE: Stumped for plans this weekend? Take a page out of KRO's book and try out these local haunts. This story was originally published on December 17.
Faces come and go in Chi-town's fast-paced media scene, but there's one that has managed to stay as fresh and sassy as ever. We're talking about Kelly Ryan O'Brien, known since her days as the PR/event guru for Gen Art to her most recent role as the founder of the Chicago Blogger Network. If you know her, you love her (hello, major Twitter following!), and if not, it's about time you became acquainted with this media darling.
Putting her social life aside for an afternoon, O'Brien took us to some of her favorite Windy City spots. Stopping by Dovetail Vintage was like a peek into her closet, and, when it comes to grocery shopping, this down-to-earth gal can't get enough of old-school Italiano spot, Bari Foods. So, click through and get to know this go-getter outside the limelight.
Photography by Anjali Pinto
Describe your style in three words.
"Hysterical, bohemian, princess."
Kelly is wearing a vintage dress, Ralph Lauren socks, and Barney's COOP shoes.
Did you always want to get involved in the fashion field (Billion Dollar Babes, Fashion Director at Stylitics, Donna Karan), or was PR/Marketing your original passion?
"I always knew I would work in the fashion world — so much so that I begged my parents to spend a high school summer at FIT in NYC. However, I didn't know what area would be my passion. It turned out that my exposure to event production and celebrity/influencers outreach at Donna Karan was where my passion really got started. From there it is has been a whirlwind of PR/Marketing and everything else in between. Having 'grown up' in such a small company, you have to learn to do a bit of everything."
Kelly is wearing a vintage necklace.
Why is Dovetail one of your favorite places to shop?
"It has an excellent curation of vintage pieces and local designer love — including some amazing statement items. Also, Julie the owner is the Bee's Knees. Pull up a chair and chat away!"
You've lived in Chicago, New York, and L.A. What are some pros and cons to all locations and which is your favorite?
"This is a tough question because I have always felt that NYC was home — it must have been in a past life. But Chicago has given me so much and I think I was meant to be here. Being from the Midwest, it is a great honor to be making a difference in my hometown — however small it may be. L.A. is beautiful, but it is hard to travel as much as I do and be based so far from family. I think it has been a long road leading me home to Chicago. Barring a surprise move overseas, I feel I will be here for a long time."
A lot of people miss Gen Art in this city. Will it always hold a special place in your heart, too?
"I didn't realize it at the time, but it was indeed a once in a lifetime experience. I feel that I 'grew up' over my five years on board. Having just been displaced from NYC post 9/11 (celeb/PR/event liaison at Donna Karan became a tad bit frivolous in the wake of the tragedy — in other words, I got laid off), I was new to the market so didn't realize the huge void the organization was filling."
"By age 24 I was entrusted with driving the mission in Chicago (and then nationally) and I always took the responsibility very seriously. I learned that anything is possible if you work your tuchus off, and that is an amazing gift to be given at a young age. As a serial entrepreneur, it was a dream to suddenly be at the helm of an organization dedicated to giving deserving artists in film, fashion, art, and music a platform that they otherwise may not have had through corporate event marketing."
"This is how Chicago Blogger Network was born. Coming back from L.A. as a blogger and social media junkie I wanted to find a way to make a difference — however small or large. I learned how to marry corporate sponsorship with opportunities to raise the visibility of a creative mind and I find that for me, it is the only way to work."
Kelly is wearing an Allsaints coat, Theory top, Agga B skirt, Pura Lopez shoes, and Falke socks.
Why is Bari Foods a special place to shop?
"I appreciate nothing more than living and working among people who are hard working, honest, and straight shooters — that is exactly what you find at Bari. It goes a little something like this: walk in, grunt an order, pay, grunt, leave, and somehow leave feeling warm and fuzzy.The sub sammies on fresh Italian bread are absolutely incredible. The area is an old Italian hood and Bari is in the DNA of this street."
Is it safe to say that Gen Art is where you developed a name for yourself in the Windy City?
"Indeed. Gen Art was my first position post NYC (and was a brand newly opened office), so there were major spotlights on what I was doing — although at the time I was not keenly aware of it. I was trusting my untested gut and throwing all caution to the wind. Part of my challenge at Gen Art was swiftly raising awareness about our mission, gaining press traction, and integrating myself respectfully into the emerging art world. The Chicago office only had two people (many people don't know that), so there wasn't much time for reflection."
"I have always had very strong business and creative voice shouting at me to create experiences (both offline and now online) that entertain with a business and creative mind, so I have found that paving my own way is the most satisfying. There is no line between me and what I do, so if I ever being to feel that there is, I immediately course correct. I don't remember a lot of sleep, eating, or personal time, but it quenched my voracious thirst for knowledge and community in a way that has only been matched by creating my own voice on social media and of course, Chicago Blogger Network."
So it seems as though you've been involved in a series of launches (Billion Dollar Babes, Michigan Ave, Donna Karan). Would you say that is your specialty? What do you like about it?
"Absolutely! There is an art form to entering a marketplace that includes an entire skill-set that I have been lucky enough to develop throughout my experiences. I adore the energy, the hope, the brand positioning…you name it."
Kelly is wearing vintage jewelry.
Tell us about the goal of Chicago Blogger Network.
"The goal of the network was filling a void I saw when returning to the Chicago market. As part of a network in L.A. and NYC, I kept asking myself how I would do it differently, and how I could use my talents to raise visibility of this new and electric market. The result was creating a space for bloggers to network and create more opportunities for exposure. In addition, it allows potential sponsors, partners, and advertisers to find the right 'match' when it comes to the projects they are working on."
How many members are there so far?
"We have over 400 bloggers in all categories — fashion, beauty, music, mommy, sports, comedy, health, fitness, foodie, and more! The website has had a couple incarnations, but we are finally weeks away from officially launching — however, the company has been very active for over a year now. Our Tumblr, Twitter, and Facebook are our mainstays of communication at the moment. Our morning Daily Dose of blogger editorial is our latest craze and has been super well received."
Tell us about your blog Idols and Egos. How did you come up with the name and what inspired you to start it?
"About four years ago I was diagnosed with a couple pretty heavy health issues that included many surgeries and took me out the 'game' for a couple of years. Since I am not great with idle time, I started documenting my journey via kellyryanobrien.com and dove into social media as a creative outlet. Idols and Egos was born to be a place for me to pontificate on all things pop culture and fashion, and get away from being just an outlet for friends and family to get updates on illness related issues."
"I have a reputation for 'interrogating' everyone I meet and have a voracious curiosity, so it is the perfect outlet for me. I think 'Idols' and 'Egos' are incorporated into the fiber of what is today's pop culture, so it describes my content pretty well. Chicago Blogger Network has taken my focus astray lately, but I am 100% dedicated to keeping it as a place for my mental 'home.'
Kelly is wearing an Agga B jacket, Nightcap T-shirt, American Apparel skirt, Missoni tights, and Prada shoes.
How does the network work?
"The site will have a separate member portal in order to streamline communication opportunities to the bloggers themselves, as well as editorial from bloggers, myself, guest editors, video content, and other great stuff. I want it to be a fun, relaxed way to get the vibe of whats good with Chicago's Blogosphere. With over 400 bloggers as members in all categories, we are in a unique position to create unique content, really only limited by time and imagination."
What do you love about the Hideout?
"Low ceilings, neon multicolor lighting, and plopping onto an ripped vinyl bench feels like home — but with cooler people (no offense dad!). I love to order Diet Coke mixed with anything. Their fountain DC is DELICIOUS. It also has Irish Roots (my people). I love this quote about the history of the place: "born as a 19th Century shanty, straight from the mud by ditch-digging Irishmen with dirty boots and hats, always hats, pushed aside by the nickel and dime Prohibition Era Sicilian button men."
Let's talk events! What are some of the best you've planned or been to in this city?
"Great question! There are SO many, but the one that stands out the most in terms of visibility was the launch of the Motorola SLVR phone in Millennium Park. It involved projections onto some of the most iconic buildings in Chicago (a red tape nightmare), a clear-span tent from which to view them, and really great celeb talent. Working with Mayor Daley and his team on the first Fashion Focus and headlining with the first Chicago Fresh Faces in Fashion Show was also an honor. Other favorites include Beastie Boys and the Roots at Sundance Film Festival, and NYC and L.A. Fashion weeks. I can go on and on!"
What trends will you be wearing this winter and what trends will you not be caught dead in?
"Although I know I am influenced by some trends, I don't often think in terms of them. I sort of just go with my gut — however weird it may be. One trend I cannot get on board with is the pointy manicure. I respect it, but I just can't do it."
Where are your favorite places to shop in Chicago and why?
"I feel most comfortable and have the best luck vintaging, no matter where I am. My favorites are Dovetail, LuLu’s at the Belle Kaye, Salvation Army, Silver Moon, and this little gem called Pretty Vintage on Chicago Avenue. But I don't discriminate — it's the thrill of the hunt! And of course, eDrop-Off and Luxury Garage Sale always have great curated key pieces. Because of Gen Art, keeping it local is ingrained in me!"
Kelly is wearing a Kimberly Ovitz dress, Allsaints jacket and Woolrich hat.
Whose style do you admire and why?
"My mom has killer style and is a bad-ass in general. Rits-Pa-Toots (Rita, her nickname) has always been able to mix it up with bargain buys and designer clothing. The older she gets, the more chances she takes. Its awesome to rip a look off of your mom!"
What is your dream piece of clothing or an accessory that you'd love to own if money was not an object?
"I honestly don't have one! I am lucky in that I don't tend to covet super duper aspirational expensive items. I think you can create a look while maintaining a relatively sane budget. I said relatively..."
What's your advice for dressing stylishly through a Windy City winter?
"Aye. The million dollar question. Invest in a great statement coat and always have a pair of Hunter Boots at the ready."
What's on your fashion or beauty wish list for Christmas?
"If there is anything I have learned over the past four years (and continue to learn), health is the best accessory. I know that sounds horribly cheesy, but, until I didn't have it, I really didn't realize it's value."
What's next for KRO?
"Fun stuff! I am working on my own line of sunglasses and statement glasses, so that is pretty insane! Also, over the summer I was approached and filmed a docudrama surrounding my life as well as other social media personalities within Chicago Blogger Network. That seems to be moving along...but that's all I can say about that for now!"
"Now that we have our 400-plus bloggers as part of the network, it is time to get down and dirty! I have taken my time to ensure a strong base here at CBN, so expect exciting partnerships and many more networking opportunities for our bloggers. What is most important is that I continue to collaborate creatively with Chicago's most creative minds, inspire my staff and help raise the visibility of Chicago's bloggers and artists."
What is one solid piece of advice for bloggers who want to get their name out there.
"Be yourself. Just write about what interests you and don't work too hard at creating your 'voice.' You already have a voice — just be consistent and be curious. That's it."