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25 Most Stylish Bostonians of 2010 -- Billy Costa

Billy Costa (Dina Rudick / Globe Staff)
By Doug Most
Globe Staff / November 18, 2010

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Billy Costa

Age: “Mid-fifties’’

Residence: Salem

Occupation: TV and radio personality on KISS 108

Most people know you as a radio personality. So why does it matter how you look? I’ve always been radio and TV. When I was in high school, I worked after school at a high-end men’s clothing store in Harvard Square, called J. Press. I was named best dressed in high school; whatever pennies I made I gave right back to the store. It hit me at a young age. Maybe because when I was really young, I was so poor, I had shoes with holes in them. I had nothing as a kid, so once I found myself in the arena of fashion, I just swallowed it whole.

Do you have a favorite shirt that’s your go-to look? When you build your wardrobe, you tend to wear a lot of the same things. As we speak today, I have on one of my favorite sports coats, and I found a great new combination and I feel like a new man. On any given day, you’ll find four complete outfits in my car. I’m a fashion geek. I do a morning radio show, then I might host a lunch, do a TV shoot, and do an appearance at night. All the things I do in one day might require a different outfit.

Is it hard today for guys to distinguish themselves with style? I don’t think most guys want to distinguish themsves. They just want to be stylish, and most men don’t know how. It seems like guys can wear a great dress shirt, tail out, and jeans and it looks great.

Where do you shop? For more than 10 years, everything I own I buy at Giblees fine men’s clothing in Danvers. I’m a North Shore guy. Within his store he’s got so many different levels. You could be going on a tropical vacation, he’s got tons of stuff. If you’re doing a black-tie event, he’s got that, too.

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