Most Stylish Bostonians
Karen Kaplan

Age: 47
Job: President of Hill, Holliday
Residence: Marblehead
How important is style to you? It's very important to me. Not just from a fashion perspective, although I do love fashion, but from a personal expression point of view. I look at it as a great opportunity to differentiate myself.
How do you typically dress at work? I'm a small person. Accessories can overwhelm me. I wear very tailored, fitted classic suits and also jackets with pants. But always with something unexpected. A special button. A special sleeve. I have a great brown pinstriped suit with pants and a cropped fitted jacket. It has a bow in the back. I like feminine things. Just because I'm in business doesn't mean I have to dress like a man.
Are you a fan of corporate casual? In my business, because it's a very creative business, the style is very interpretive. We are open to that. I see a lot of people that wear jeans here. I tend to dress appropriately for my clients. If I go to a bank or insurance company, I dress accordingly. I am very comfortable with others dressing casually. I prefer not to.
As a female president, what message do you try to send with your wardrobe choices? The whole idea of power dressing -- I feel like that's what business cards are for. I'm a woman. I like to dress in a feminine way. I don't feel that there's any need to sort of moderate my style because most of my peers are men.
When do you find time to shop and where do you go? I squeeze it in. Working in the Back Bay, I can run in and out. I can squeeze something in in 20 minutes. I really enjoy shopping. I love Nanette Lepore on Newbury Street. Sara Campbell in the South End. Neiman Marcus. When I travel, I shop.
What's the most indispensable item in your closet? I have a winter coat. I saw this coat in Neiman Marcus a couple of years ago. I fell in love. I visited it every day. It's black cashmere. It's belted. It has a ruffled mink collar. It's very glamorous and chic. Women literally roll down their windows at stop lights and ask me where I got it.
How large is your closet? I do have a large closet. It's a walk-in. I have what my family calls a wall of shoes. I have a cedar closet downstairs for the off season.
Do you keep track of fashion trends? I'm very aware of trends. Part of my business is staying on top of trends and popular culture. I will embrace trends that work for me. I focus on what's flattering to my figure. If you don't change your look often and your shape doesn't change very much, you should be able to get several seasons out of good quality clothing.
Whose style do you admire? My mother. She taught me the importance of style and developing my own unique style young. She is and always has been very well put together. My daughter is 14. She was born with a great sense of style. We have pictures of her when she was a toddler. She accessorized the hat and the shoes.