Have you ever known someone so well-dressed you couldn’t wait for them to arrive? When I was in grade school, that person was Kelly Hefner. Her mom owned the Pee Wee Shop on the square in Benton, Illinois where we grew up. The shop was founded in 1969 and is still there. I have no idea what it is like now, but back in the day, the Pee Wee Shop offered the finest children’s apparel in Southern Illinois.

Kelly and her older sister were like walking billboards for the store. I use to imagine Kelly getting dressed each morning, standing in front of an endless conveyor belt. She would push a button and let the line run until she saw something she fancied. How I wondered what it might be like to live in Kelly’s clothes!

Two things I promise you about the stylish Hefner girls: 1) their clothes were several cuts above my Montgomery Ward and Sears wardrobe, both in quality and originality and 2) neither Kelly nor her sister wore the same thing twice. I used to wonder what happened to all their clothes. Realistically, maybe Kelly got a few of her sister’s hand-me-downs or maybe they gave them away to needy families. Not that there’s anything wrong with hand-me-downs because that is the whole idea behind vintage clothes: they are clothes too great for just one lifetime!

Over a lifetime, there have been a lot of Kelly Hefner’s in my life—people I couldn’t wait to see for their amazing wardrobe. I’ll bet you have a few of your own. Why not share your favorites with us? Not the Cocos, Jackies, and Audreys of the world—but real people that are on your A list. Send us your story of someone whose sense of style always wowed you. The winning entry will get to choose any vintage pin from a collection we’re introducing the week before Christmas. To enter, you can submit your comment here or send us an e-mail: crystal@dressedherdaysvintage.com

Now for a girl who wasn’t afraid to make her own fashion statement, my very original niece Sarah. Wouldn’t it be wonderful if we all retained some of the freedom that youth gave us to be expressive?

My niece Sarah: She was only five here and already a free spirit. When's the last time you thought of wearing a rubber glove as a shoe?