Best Dressed Winner: Jennifer McClure

417 Magazine: What three words define your personal style?
Jennifer McClure: Classic, preppy (laced with a healthy dose of irony) and plaid.

417: What is your favorite fashion trend right now?
J.M.: My favorite fashion trend, purely in the bubble of my own existence and with no relationship to the actual fashion industry of the present, is wearing saddle shoes. They are really the unsung hero of footwear—at least I am not aware of any songs about them. Nostalgic simplicity.

417: What is the most embarrassing thing you’ve ever worn?
J.M.: In one of my high school senior pictures, I wore a puffy, ruffled white dress that made me look like a human-sized meringue. A cooking experiment gone awry.

417: Where do you find inspiration for your closet?
J.M.: Seven Sisters Style book, old photos of my mom, walking through the men's suit department—great patterns and textured fabrics there—and in any shoe store or shoe department. [I search both] brick and mortar and online.

417: Who are your fashion role models?
J.M.: Diane Keaton, Doris Day, Grace Kelly, my mom, Ralph Lauren (during the ’80s), Blair Warner from the Facts of Life sitcom and G.H. Bass.

417: What person—public figure or private citizen—would make your best dressed list?
J.M.: My mentor, Roseann Bentley. She has a timeless, elegant style.

417: What’s your signature piece?
J.M.: Anything plaid.

417: If you could wear one brand or designer for the rest of your life, what would it be?
J.M.: Brooks Brothers.

417: Where are your favorite places to shop in 417-land?
J.M.: Dillard’s, 5 Pound Apparel (quirky and fun), Culture Flock (best T-shirts), Plaza Shoe Store and the Vision Clinic (great eyewear).

417: What one item is on your wish list for this year?
J.M.: I’m torn between Rowing Blazers’ Princess Diana sheep sweater (original design by Joanna Osborne and Sally Muir) or the J. Press “Shaggy Dog” sweater in Kelly green.