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I bought a dress online, a long black summer dress that I thought would make me look earthy and graceful.

Dresses are foreign to me but I keep trying, like all the years I kept going back to Spanish classes thinking this next time I would become completely bilingual. Buenos dias!

The dress, so chic and classy in the photo, could double as an emergency tent. It's that voluminous and heavy. Maybe it's water repellent, I don't know. It's a lot of dress, folds and folds of black with a high elasticized waist. It makes me look like a yak herder's widow on her way to milk the yaks. So I stuffed the dress in the back of my closet in case there's a war or something where I need to cloak myself, you know, and dash from building to building unseen in the dark.

The other dress I bought online was because, on the model, the skirt was twirling. It looked merry and carefree and I thought 'that could be me!' When it came, I stripped down and tried it on. Oh Lord. it was my grandmother, Millie. Millie in her triple D cups, the belt of her dress cinched tight five inches north of her waist, her skirt flared as she stepped back from putting her potato salad on the picnic table. Just potatoes and eggs and onions and some mayo, just enough to hold it together, to pack it like a snowball in case there's a fight with other folks at the park.

Today, in my weeks-long effort to clear my office of 25 years of projects, photos, kids' homework and tax files, I found this incredibly accurate drawing of me done by my granddaughter. You'll notice I am a mermaid, wearing a slight pink bra, my long blond hair gathered not once but twice by black ties. I have green fins and the world's bluest eyes, saucers of eyes, because clearly I am happy. I am smiling. Who wouldn't be? It's the perfect outfit.

How we see ourselves, how others see us, how much we think about this or don't. We love the times when we don't think about it and that's usually because we are being safe and timid in what we're wearing. Camouflaged by the safe. I want to change that, break out of taupe, eschew my rivers of pants, twirl a little. I yearn to go milk the herd with flair and style.

- Jan Wilberg

Jan Wilberg writes about everything from national politics to outwitting rats in the basement with the help of her two sons. She is a mother, grandmother and a formerly hearing impaired person rejoicing in the miracle of her new cochlear implant. Her blog Red's Wrap has a tagline that says it all: Happiness. It's relative.