I first met Aramide Esubi of The Sassy Peach fashion blog when I hosted the open call street-style shoot with for the Refinery29 Winter slideshow. I was instantly charmed by her warm personality and unique sense of style. I asked if she’d be willing to meet up with me again so I could photograph her for my own blog. Right before I left for New York fashion week, I caught up with Aramide in Millennium Park. What venue in Chicago is more perfect for a produced photoshoot? Yeah, that’s right. NONE. I love it when my subjects are game for an adventure, so we hiked up to the top of the Art Institute bridge to take some photos. It was a win-win situation; I got to practice professional portrait photography and Aramide has lovely photos for her blog. She’s originally from St. Louis on the edge of the Ozarks. We have that heritage in common, especially considering most Northern Arkansans root for the Cardinals (and not the Royals). There’s this weird thing about Northwest Arkansas where it’s exactly 5-6 hours to a real city in any direction; Dallas, Oklahoma City, Kansas City, St. Louis, and Memphis. Most Arkansans “adopt” one of those cities and for my family it was St. Louis.

Why? Because Little Rock still doesn’t have any major league teams or a highly developed luxury retail market, so many Arkansan families will travel to one of those bigger cities to do serious shopping at “fancy” department stores, to visit museums, and to catch pro sports games. Before the explosive growth of Walmart in the past 2 decades, NW Arkansas didn’t have any world-class cultural institutions outside of the University of Arkansas, but that’s changing (oh hai thar, Crystal Bridges…). Most long-time Arkansans preferred Dallas, but for us “transplants” it tended to be St. Louis. I grew up traveling there a lot since St. Louis is the most Northern – culturally and geographically – of those cities. I know it reminded my parents of home back on the East Coast. It doesn’t surprise me that a woman as stylish and cosmopolitan as Aramide came out of St. Louis; along with Madison, Wisconsin these two cities are my favorite satellite Midwestern conglomerations. Sorry, Indianapolis…

Aramide is currently working as a personal stylist and consultant. She’s also looking to collaborate with more established stylists in the Chicago area. Follow Aramide on Twitter, @TheSassyPeach, and make sure to check out her Facebook Page.

Preetma Singh is a Vogue fashion editor/assistant whose style I also have a huge crush on. When I photographed her at New York fashion week last week I instantly thought of the Barneys department store slogan: Taste, Luxury, Humor. The T-shirt could be Undercover has been successfully identified as Meadham Kirchhoff and is available on Net-A-Porter. There’s a smirk here, and I’m not talking about the actual smile on her face. Its the unexpected combination of a drop dead beautiful woman wearing such an exuberantly fun look at New York fashion week, where everyone is normally SO. SERIOUS. about their outfits. The striped gloves and plaid collared shirt only heighten the delightfully “off” vibe. If only everyone had this much fun with fashion.

What intrigued me about Ben’s look was his use of bright colors. Bubblegum pink and cerulean blue flannel aren’t colors I normally see men mixing together, but it works well layered under the vintage corduroy coat. I’m also really loving this trend of manly men wearing coats or jackets with wide lapels made of fur, either mink or faux. I wish more Chicago men would have the courage to play with prints and textures.