Dressed for Success: What Chicago’s Most Stylish Professionals Wear to Work

Every Monday morning, we all ask ourselves the same question: What should I wear to work today? To help solve that perennial dilemma, we got some of Chicago’s most stylish professionals to share their secrets for looking good while climbing the corporate ladder (hint: excellent tailoring is key). Here are their tips – plus a look at some of the chicest office-appropriate fashion for fall.

Photos by John Reilly

Clothing styling by Evangeline Politis

Make up by Cory Deking of 10 MGMT.

Hair by Mindy Snyder of Teddie Kossof Salon

Kim R. Jenson

UBS Wealth Management Americas, Chicago Complex, Managing Director

Go-To Work Outfit

Works in: Chicago

Lives in: Chicago (Lakeview)

Style icon: Jackie O‘s “elegance in simplicity.”

Go-to work outfit: Sleeveless dress with a jacket.

Q: How do you combine fashion and functionality in your work wardrobe?

A: Managing our clients’ wealth is serious business. So, I dress professionally every day.

Q: Why do you think it’s important to dress for success?

A: You are the brand. It is critical to present yourself in the way that you want to be perceived; for example, professional, approachable, respectful.

New Fall Look

On Kim:


Mark Rector

Lloyd’s of London, U.S. Project Manager

Go-To Work Outfit

Works in: Chicago

Lives in: Chicago (Logan Square)

Style icon: Addison DeWitt (from movie classic “All About Eve”)

Go-to work outfit: Dark blue striped bespoke suit, blue striped shirt with French cuffs, cuff links, purple tie, purple patterned pocket square, purple socks, black monk-strap shoes.

Q: How do you combine fashion and functionality in your work wardrobe?

A: Gentlemen are expected to wear suits and ties at the Lloyd’s market in London, which I visit for work at least twice a year. I’m most likely to be in a suit here in Chicago. I get classically styled bespoke suits and shirts from Tom James, which I jazz up with assertive neckties, complementary pocket squares, colored socks and vintage cufflinks.

Q: Why do you think it’s important to dress for success?

A: Nobody wants to do business with a hobo.

New Fall Look

On Mark:

All pieces from J.McLaughlin, 847-784-1730

  • Sweather, $135
  • Italian silk tie, $95
  • Beekman shirt, $145
  • Pima cotton pants, $175


Jamie Stein

Sears Holdings Corp., Communications/Vice President PR and Member Communications

Go-To Work Outfit


Works in: Hoffman Estates

Lives in: Glencoe

Style icons: Olivia Palermo, Jamie Chung, and I am obsessed with the style of two TV characters—Alicia Florrick (“The Good Wife,” costume designer Daniel Lawson) and Olivia Pope (“Scandal,” costume designer Lyn Paolo)

Go-to work outfit: A fitted, sleeveless black dress and nude pumps. I have one by Theory that is A-line cut, one by Tahari and an old one by Calvin Klein that my tailor helped me remake. A black dress is polished and chic and makes a statement without making a statement.

Q: How do you combine fashion and functionality in your work wardrobe?

A: For me, it’s all about what makes me feel good – and that is usually a mix of comfort and style. My workdays are long and involve running from meeting to meeting, making presentations and sometimes a dinner or event. Dresses are easy. I like a dark jean, tank and blazer with sleeves rolled up. When I travel, I wear flats.

Q: Why do you think it’s important to dress for success?

A: When it comes to dressing for success, you’d better look the part or you might not get the part. People definitely do judge a book by its cover, especially in business. Clothes make a strong visual statement about how you see yourself and impact how others perceive you.

New Fall Look

On Jamie:


Jetta Boschen

Promojett Services, Inc., Owner

Go-To Work Outfit

Works in: Winnetka (and wherever my clients are based)

Lives in: Winnetka

Style icons: I have found my style inspiration from many “icons” throughout my life. In particular, Lilly Pulitzer (I even named my dog after her), Lisa Birnbach (“The Official Preppy Handbook” was my bible growing up), Reese Witherspoon (her southern style), and Diane Von Furstenberg (I like that she has really gone out of her way to empower women through her many philanthropy projects).

Go-to work outfit: Black wrap dress, statement belt (Gucci), scarf (Hermès) and boots. Sometimes I substitute the dress for black pants with the same accessories.

Q: How do you combine fashion and functionality in your work wardrobe?

A: I like very classic, simple clothes that I can incorporate accessories into for my busy lifestyle. I often have several client functions a day and need to adapt my outfit accordingly. I also love color (bold prints/patterns) and use it to brighten my spirits, especially in these dreary Chicago winters.

Q: Why do you think it’s important to dress for success?

A: I was raised in the south, and attended schools that required coats and ties for boys and dresses for girls. That southern influence has always impacted my wardrobe choices. When one is dressed up, I feel one garners more respect and commands attention. To this day, I feel more comfortable in a dress. I didn’t even buy my first pair of jeans until I was 40!

New Fall Look

On Jetta:


Rachael Halstuk Mangoubi

Mesirow Financial, Vice President, Wealth Advisor

Go-To Work Outfit

Works in: Highland Park and Chicago

Lives in: Chicago

Style icons: I don’t have a primary celebrity style icon! I am most inspired by the people around me – my friends, family, people I see on the street, people I see in magazines, people I see on TV. I love collecting ideas from what I see around me and then I try to reinterpret them in my own way. And, in a bit of a role reversal, my husband has exceptional style. I have learned a lot from him and I get a lot of inspiration from him.

Go-to work outfit: Almost always a dress! I have a number of unique yet understated dresses that are my go-to outfits for important meetings and presentations. I also always choose something that I believe suits my audience. While I view fashion as my personal expression of style, I also strive to dress for my environment, to fit the seriousness of the occasion, and to make others feel comfortable around me.

Q: How do you combine fashion and functionality in your work wardrobe?

A: Layering is a big thing for me! I adore putting a collared white shirt under dresses, and I do so even when that would be an unexpected look. It is a great way to take a dress and make it more serious or give it more depth than it would have on its own. As for shoes, I cannot wear a work heel that is more than 3 inches. My new favorites actually are 2-inch heels, and they feel so elegant and fresh to me. Plus, I can walk a long way to meetings in them.

New Fall Look

On Rachael:

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