Local Arts Patron Karen Drummond Is ​​​Always in Fashion

Local Arts Patron Karen Drummond Is ​​​Always in Fashion

A few rotating stellar pieces are all it takes for local arts patron Karen Drummond – and you – to stay confident and timelessly stylish.

Karen Drummond believes the foundation of great style is knowing who you are. Everything else – designer clothes, vintage accessories, travel finds –is simply extra. Drummond credits her chic ensembles to a life surrounded by art, which continuously sharpens and refines her tastes. At age 85, she feels as in tune with herself, and her style, as ever. 

She draws inspiration from her worldwide travels, filled with stylish strangers, gallery visits and live performances. Though her influences are wide-ranging, her wardrobe is anchored by classics. “At this stage of my life, I shop my closet,” she says. Her collection is a living capsule of her life, one that keeps her looking effortlessly in style. 


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Photo by Aliza Baran

Make a Statement 

Though she gravitates toward understated tones, Drummond knows the impact of a bold accessory. She loves these red Jeffrey Campbell boots so much that she bought them in white, too. 

Circling Trends 

 Polka dots may be trendy now, but Drummond knows they’re timeless. After decades of collecting, she’s seen countless styles cycle back. When they do, she often already has them in her wardrobe – a testament to fashion’s rhythm. “Great pieces come back around, and I mix them with something new to keep things fresh.” 

Invest in Quality 

Drummond values high-quality wardrobe staples, like this brown genuine leather jacket from Rag & Bone she purchased last year. Ensuring a piece’s longevity starts with understanding fabrics and garment care, skills Drummond learned while working as a textile specialist for a children’s clothing designer. Whenever Drummond does buy new, she goes for first rate – something that will stand the test of time like the rest of her collection.  

Pull From Your Archives 

A great way to stay stylish is to build a capsule wardrobe filled with versatile, mix-and-match pieces, like these slim-cut black trousers. Drummond says it’s not always necessary to buy something new. “I look for pieces that can go anywhere, anytime, and always feel like me.” 


The cover of the February 2026 issue of Milwaukee Magazine

This story is part of Milwaukee Magazine’s February 2026 issue.

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