ESQUIRE Jay McBride's winning look, re-envisioned by Esquire editors: Armani Collezioni two-button wool jacket ($1,295); Gant cashmere sweater ($275); Kenneth Cole cotton shirt ($89); Diesel jeans ($149); and Coach suede sneakers ($190).

---

Islander is in Esquire’s
best-dressed finals

The doctor, who arrived here
recently, wore his grandfathers’
apparel in contest preliminaries

Does Esquire know? After Jay McBride was chosen as a finalist in the magazine's "Best-Dressed Man in America" competition, he up and left Boston to start a new life in Hawaii, a move that necessitated a change in his winning style.

Right now, the vintage wool jackets he loves and wore during the selection process are sitting in a Matson container waiting to be picked up, while McBride has grown accustomed to kicking back in surfwear and khakis.

McBride will appear on "The Today Show" next month, and the public can vote on their best-dressed choice online at www.esquire.com.

"My girlfriend tried to get a lot of votes because the prize is a Chrysler Crossfire and she wants it."

McBride models his former look on the site. He's looking tanner since moving to Hawaii a month ago, but whether suited in Boston or in surf threads in Hawaii, McBride's always been true to his sense of comfort and wearing what feels natural, opting for personal style rather than fashion for fashion's sake.

He'd be the last sort of person you'd expect to enter a best-dressed contest, and admits the way he entered was "sort of random."

"I read Esquire, but I didn't find out about it in the magazine. I was watching 'The Today Show,' and they were interviewing the winner from New York and said they were gonna be at Macy's a mile from my home, so I went over there after work and was surprised when I made it to the final 10, and then when I was picked to be in the final five. It was kind of bizarre, and now it's blown up into this big thing that has since gotten out of hand.

"I'm not a very outgoing guy, and this has caused a lot of attention that I'm not used to."

FL MORRIS / FMORRIS@STARBULLETIN.COM Jay McBride goes casual outside his apartment near Diamond Head.

His daily uniform comprises scrubs and clogs, and when off-duty he relaxes by surfing, heading to the ocean in board shorts and a Billabong T-shirt.

"I'm definitely not a shopaholic," he said. "I'm more of a thrift-store shopper. I don't think I own any article of clothing over $100."

The clothes he's modeling on the Esquire Web site are "a little over the top," he said, but represent an editor's approximation of what he wore to his audition. Those included his grandfather's Hudson blazer, which came out of Detroit in the 1940s, and his other grandfather's white-top saddle shoes from the 1930s.

He paired the vintage pieces with simple boot-cut Diesel jeans emboldened by a checked purple shirt and argyle V-neck sweater.

"(My grandfathers) both died a while ago. I always respected their sense of style and the way they could throw together a look that was casual but cool. They were very low-key and dressed to carry themselves with dignity.

"It makes me proud that I won wearing my grandpas' clothes; it's sort of a tribute to them. But I also like to do my own thing, and if I should win, if I have any say in the matter, I will ask to go with Hawaii style, what I'm wearing now. I love it."