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Legal Executive Amy Osteen Blends Vintage With Modern for a ‘Give and Take’ Style

The Outside CLO principal isn't afraid to defy expectations for lawyer fashion.
| |Photography by Jin Kim

Amy Osteen is a legal industry business leader whose company Outside CLO provides fractional chief legal officer and general counsel services as well as labor and employment law guidance to companies in need.

Some lawyers try their best to have their fashion be as forgettable as possible, but Osteen has taken a different approach. Encouraged by her husband, who worked in the high fashion industry for decades, she isn’t afraid to defy expectations for legal fashion. Read on to learn more about her go-to look, what inspires her everyday fashion choices, and how her wardrobe transitions from work to play.

What I Do: “I’m the founder of Outside CLO, a collection of former in-house counsel and C-Suite executives who help hyper-growth and middle-market technology companies scale.” 

Style Icon: “My husband, Michael Gulley. He was in the fashion industry for two decades, fronting campaigns for high-fashion and high-street brands alike.”

On The Job: “Clothing and perception are linked. That’s why most lawyers will wear their best black suit to an important meeting or event. If you occasionally break the status quo, people notice and admire it. So, I might show up to dinner in my best black pantsuit, Metallica t-shirt, and red heels.”

Fashion Ispiration:“I’m making a more conscious effort to shop local, shop small, shop sustainable, and shop quality over quantity. Our choices around what we wear have profound implications for our communities and planet.” 

Style Defined: “Some call my style ‘tomboy chic.’ My friend, Fancy, calls it ‘self-deprecating.’ I call my style ‘give and take.’ Part of me likes tradition and history, hence a love of solids and neutrals. Part of me wants to break the rules.”

How I Accessorize: “Cuffs, especially worn as a set. I’m sure it’s a phase, but for now, it’s Wakanda forever!”

Go-To Look: “A blend of new and vintage combined with ankle strap high heels or combat boots.”

Favorite Stories: “When traveling, I always find a Reiss because it has a non-frumpy petite line. In Dallas, you’ll find me at local shops like Favor the Kind, Reformation, Clotheshorse Anonymous—and raiding my friends’ closets.” 


Brandon J. Call

Brandon J. Call

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Brandon J. Call is the former executive editor for D CEO magazine. An award-winning business and data journalist, Call previously…