Since moving here last summer to serve as executive director of the Rochester Downtown Alliance, Holly Masek has been greeted with some pleasant surprises.

"Walkability," she said, is among those. "And my new neighborhood in Historic Southwest. I love how varied the houses are there. It reminds me of a favorite children's book of mine, 'The Big Orange Splot.'"

Masek, who's originally from New Hampshire and spent her career before now in Boston, reports that other favorite things include travel, cities, hiking, sleeping, plants, defending her yard from rabbits, food -- eating, not cooking.

"I like learning new things," she added, "and so far in Rochester I've attempted wheel throwing at Earthbound Designs and tennis at Rochester Tennis Connection. Looks like I will be keeping my day job on both fronts." 

How do you describe your style?

Simple and classic. 


As a kid, I watched old movies from the 1940s through the 1960s with my grandmother -- and I loved the style and silhouettes women wore in those decades. Everything from structured evening gowns to mock-neck, black turtlenecks and high-waisted, belted trousers. I hated every second of the low-rise denim era.

Other lessons in style?

Maybe one of my biggest style influences was my freshman year roommate. I came from New Hampshire with Birkenstocks and she arrived from Washington, D.C., with stiletto-heeled boots, pearl earrings and about 30 sweaters that she kept neatly folded and sorted by color. She taught me about "going out clothes," the language of high-end handbags -- I do not own any -- different accessories for different occasions, judicious pops of color.

What do you hope your style communicates?

I hope my work style says, "I came to slay." Or at least, "I am a capable and practical person who likes understated but nice things."

Dressing for workplaces is much more challenging for women than it is for men. The expectations are often unclear, the shoes are usually uncomfortable, our grooming is more complicated, and no matter what we do, we feel judged anyway. I’ve found that by keeping it relatively simple and conservative -- and by having a closet of at least five go-to outfits I feel confident in -- I can at least remove the morning "what to wear?" hassle from my day and turn my brain on to other things.

What should every well-dressed woman have in her wardrobe?

A well-cut professional dress with sleeves -- preferably made of a forgiving fabric, meaning no Spanx required. This is her emergency dress for those days when she needs to quickly get out the door feeling put together, but doesn’t have the bandwidth to assemble an outfit with multiple variables. 

And for the outdoors? 

While I have plenty of work-appropriate trench coats, flats, dresses, etc., outdoor gear frequently sneaks into the rotation. I love a good technical garment. And I have strong opinions on wool socks. I can happily spend hours in Sierra Trading Post or REI…

Favorite accessories?

I recently scored a brown leather bucket bag from Mexico at Oronoco Gold Rush Days. It was $15 and is easily the most complimented thing I own. Long-term favorite is a pair of caramel colored Cole Haan Chelsea boots. They’ve been out of production for years, but I find them on eBay. I am on my third pair. 

Is there something especially "Minnesota" about your style?  

Besides my Rochester-issue backpack? I think my wide range of outerwear. People have picked on me for the number of coats I own, but I believe there is actually enough weather variety in Minnesota to justify them all. Perhaps I belonged here all along. 

Advice for readers?

Ignore trends unless they truly resonate with you.

People have picked on me for the number of coats I own, but I believe there is actually enough weather variety in Minnesota to justify them all. Perhaps I belonged here all along.