Menu Join now Search

Learning to Shop After Fifty

No, I haven’t been in a convent for the past thirty years but let’s just say that clothes shopping was something I did only when I ran out of socks and underwear or had to go to a wedding. Otherwise, I was very happy to pick up used apparel that I needed at the Goodwill or St. Vincent’s.

All was well until I returned to my hometown of Chicago a few months ago. Not only am I living  in an urban environment after a long absence, I am living with my mother and  in close proximity to all four of my siblings. My younger sister in particular is an avid shopper and stylish dresser. In either an inspired or deranged moment I told her that I was contemplating adopting a more urban look and would welcome her assistance.

A few days ago over a couple glasses of wine the plan emerged. She asked me to trust her, and think outside my comfort zone and be flexible. Since I am trying on some new elements in my life, I thought it couldn’t hurt to try on some new clothes too. It was fun for the first fifteen minutes or so. My sister acted as my personal shopper selecting the clothes, bringing them to the dressing room and giving the article thumbs up or down. I am organizationally challenged so spent a lot of energy trying to remember what fit, what looked terrible, etc. The first article I had to decide on was a bra to replace my way too saggy one. I had become very comfortable with the look of my non supportive bra and am not at all sure what to think of my current more buxom appearance. I bought one bra, three tops, one pair of long, boot cut jeans, one pair of denim capri’s, one pair of cropped pants, one tailored denim jacket and one pair of shoes. I spent more money than I did for my wedding thirty years ago. For that occasion, I wore a plaid, cotton button down summer dress. Maybe you get the picture.

The fun isn’t over yet. Next week I go to my sister’s hair stylist. Currently, my grey streaked hair falls several inches past my shoulders. I look forward to low maintenance short hair but my beloved sister is determined that I also get it highlighted a bit. The last time I altered the natural color of my hair was when I was fifteen and sprayed something on it in the summer to aid the sun’s natural bleaching process. It is hard to figure out why I am putting myself through this. Will I feel more attractive when all is said and done or will I feel like I am trying to don someone else’s life style? Will the “new me” attract the kind of people I want in my life, or will it attract people who will be aghast when they discover  who I really am. I am not trying to fit in. I am happily passed that. I am just trying a new appearance on for size, as they say, whoever they are. Speaking of appearance, my sis can hardly wait to introduce me to the wonders of make up.

“Country roads, take me home. To the place I belong …”

More You'll Love

Close