At CEO (Boardroom Media) we track over 1,000,000 startups and over 5,000,000 people who hold key positions in these companies. We use this directory of startups to highlight top employees, founders and board members we think deserve more appreciation than they are currently getting.
This list showcases the top Chicago based CEO’ operating in the Fashion space. If you think a CEO’ is missing from this list, feel free to contact our editor on [email protected].
The individuals on this list have been included because of exceptional performance in one of the following categories:
- Innovation – Operating as a key part in an extremely innovative business or startup.
- Growth – Operating as a key figure in the growth and upscale of a market leading business or startup.
- Management – Showing exceptional management skills.
- Societal impact – Putting their business on the map for their positive societal or environmental impact.
Our Data – We source our data from OSINT (open source intelligence) and public directories such as Crunchbase, SemRush and many more. The data from these sources should be treated with a degree of caution and verified yourself.

Monica Royer
Founder & CEO of Monica+Andy
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About Chief, Monica+Andy: Monica+Andy is an operator of an online baby clothing shopping platform.
Aaron Sanandres
Chief Executive Officer & Co-Founder of Untuckit
Aaron Sanandres is the CEO at UNTUCKit. He was also a partner at Pricewaterhouse Coopers.
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About Untuckit: Untuckit is a New York City-based direct-to-consumer apparel brand.
Kwaasi Djin
CEO, Founder of Steelo
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About Steelo: Steelo is the place to shop for the clot

Todd Brook
Founder & CEO of envisionit
Todd Brook i s Founder & CEO at Envisionit Media.
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About Engagement Multiplier, envisionit: Envisionit is a digital marketing agency that provides data, analytics, tracking, optimization, and targeting solutions to its clients.
Joe Sclafani
CEO of REV UP BRANDS
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About Global Recruiters Network, REV UP BRANDS: REV UP BRANDS is a manufacturer and wholesaler of dance apparel, costumes and accessories from Chicago.

Jeff Cheng
Founder & CEO of Runchkins
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About Runchkins: Runchkins is a personal styling service for kids clothes and accessories that guarantees to buy back everything when outgrown.

Todd Gabel
Founder & CEO of Toddy Gear
Todd Gabel is Founder & CEO at Toddy Gear, Inc..
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About Toddy Gear: Toddy Gear is a tech accessories brand, manufacturing microfiber, antimicrobial solutions that deliver better ways to clean touch screens.

Sonny Balani
CEO of Balani Custom Clothiers
Sonny Balani has re-imagined the custom clothing experience as it applies to today’s client. He has designed a contemporary showroom and developed a collaborative selection process, establishing Balani as the premier custom clothier in Chicago.
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About Balani Custom Clothiers: Balani Custom Clothiers provides exceptional clothing and consultation services with an emphasis on sleek and modern presentation.
Lindsay Wasson Lingle
Founder & CEO of Holly & Tanager
Lindsay Wasson Lingle currently works as the Founder and CEO for Holly & Tanager.
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About Holly & Tanager: Holly & Tanager is a female-founded lifestyle brand that specializes in the production and design of handbags, backpacks, and accessories.

Christina Marshall-Valdez
Founder | CEO of Elu
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About Elu: Online made-to-measure apparel brand that use smart technology to enable fit, style and customization.
James Clifton
Founder & CEO of The Locker Shop
Jim Clifton is CEO & Founder at The Locker Shop.
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About The Locker Shop: The Locker Shop provides graphic design services for the custom apparel industry.

Leslie Wong
Founder and CEO of Burgundy Fox
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About Burgundy Fox: E-commerce brand empowering women to celebrate themselves by curating intimate apparel based for all sizes.

Brian Dale
Founder and CEO of RunRunRun
Founder and CEO of RunRunRun.com
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About RunRunRun: RunRunRun is a leader in eco-friendly totes and accessories.

Annie Mohaupt
Founder and CEO of Mohop. Leader in on-demand custom manufacturing. of Mohop
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About Mohop: Mohop manufactures mass customizable footwear by combining on-demand 3D digital fabrication with emerging body scanning technology.

Annie Mohaupt
Founder and CEO of Mohop. Leader in on-demand custom manufacturing. of Mohop
Follow Annie Mohaupt:
About Mohop: Mohop manufactures mass customizable footwear by combining on-demand 3D digital fabrication with emerging body scanning technology.
Dina Patel
Co-founder & CEO of Didi’s Wardrobe
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About Didi’s Wardrobe: Didi’s Wardrobe is a platform that connects buyers and sellers of new and used Asian merchandise.
Dina Patel
Co-founder & CEO of Didi’s Wardrobe
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About Didi’s Wardrobe: Didi’s Wardrobe is a platform that connects buyers and sellers of new and used Asian merchandise.