Most Stylish Bostonians
Alex DeWinter

Age: 29
Job: Wine director at Grill 23 & Bar
Residence: Marblehead
>strong>Who do you admire most for their style? My father. He had been in the retail business for about 45 years when he retired recently. He was at Marshall Fields, he helped open Bonwit Teller in [what's now] the Louis Boston space, and he worked at Saks. Being an 8-year-old kid and seeing your dad dressed up in a suit every day, that left an impression.
What was his style? The guy can't dress casually. Put him in a tux or a suit and he looks like a million bucks.
What's your own style philosophy? I live by the philosophy that you can never be overdressed. And usually, I am overdressed.
What was the last thing you bought yourself? The other day I bought myself a sweater at this flea market in Pittsburgh for $35.
In your job, how does your look come into play? I come to work every day in a T-shirt and jeans. I never even owned a suit until I started working [at Grill 23]. In my job, I meet a lot of winemakers whose lifestyle is much more casual, so they're not in suits either. But when I'm on the floor, a suit is all I'll wear.
How do you feel about the way diners dress today? They're so underdressed. It's terrible. You can be casually dressed and not be sloppy but we often get guys who come in wearing jeans. When I grew up, going out to dinner was a special occasion whether it was a place like Grill 23 or a local Chinese restaurant. You didn't go out in jeans. No one should ever be uncomfortable in a suit in a nice restaurant. But now, I think it's changed. It's too bad.
If you could nominate someone to be one of the 25 most stylish Bostonians, who would it be? One of my [wine sales] reps, Roy Goldstein. He is Mister Retro. He wears coats and shirts from the 40s. I think he must get everything from a vintage clothing store. His style is very well thought out.

ERIN BYERS MURRAY