Finding the happy medium between Matron and Floozy

I live in a little big town and don’t have occasions for cocktail dresses but this summer I found myself in need of a cocktail dress. Now before you feel sorry for me, thinking I don’t possess a single cocktail dress let me assure you have a several. I just didn’t like the way I looked in them

Who the Hell knew shopping for a cocktail dress would be so painful? I had a very strict budget of less than $150 and it had to work with shoes I already have. But that wasn’t the cluster fuck:  Finding dresses that didn’t make me look like a Mother of the Bride or worse a pathetic old thing trying to recapture her lost youth were the bigger hurdles.

I’m not one to shop with a posse of women nor would I ever in a MILLION years subject a male partner to shopping for something so specific. Nope, I go out on my own and just get it done. But isn’t technology grand? My best friend was away and so I sent her pictures of the dresses that didn’t make me want to cry for my lost youth or puke. After dress number five she let me know she was sitting in a hotel bar with a couple of men and they were also offering opinions. Fantastic, dressing room selfies shared with strangers. Good thing I didn’t get ridiculous and naughty, huh?  I was horrified at first but these guys proved to be very helpful. It was good to have a man’s opinion. Especially a man’s opinion that wasn’t something in the range of: “Oh honey you always look good so just find something you like. . .” Because that’s what my loyal and very astute boyfriend would tell me.

My selections in the dressing room that night ranged from sequins which wore me and screamed “Here’s the Mother of the Groom and she is pissed at her new daughter-in-law” Scuba knit dresses which cling to me in all the right places and show off my work at the gym but I was worried the air of desperation these dresses take on would clash with my lipstick. I found some nice lace dresses but they were more for the polite cocktail party at the country club rather than a debauched evening in New Orleans. The dresses I selected that were vaguely age appropriate–if you squinted real hard–from the junior’s department made me look trashy and pathetic. Most “fit and flair” dresses make me look like Bette Davis in Whatever Happened To Baby Jane. Not a good look on anyone. I was about to give up when I tried on a lovely empire lace bodice and black a-line dress. Very simple, no flashy bling or daring decollete. I loved it and had a little happy dance in the dressing room before I sent it to my friend and our new best friends at the bar in Memphis. They loved it, too! Woohoo! Mission accomplished.  I could send back the other FOUR dresses I had purchased online and go home with this one.

When did buying cocktail dresses or any dress for that matter become so hard. I hate the loud prints in cheesy polyester. Whatever happened to a simple silk sheath in a subtle print that doesn’t look like the inside of an acid fueled Hunter S. Thompson dream?

And I’m not necessarily super preppy and Lands End wear makes me look like an aging gym teacher. Nor do the flowing Eileen Fisher type things suit me. Plus I don’t spend 195 bucks on blouses. And big nope to the hippy gauze skirts with earrings touch my shoulders. Not a baby boomer and not a hippy.

Good thing I work from home because I can wear my usual skinny jeans and tee shirts or my shorts and tee shirts. Or nothing. (I’m gonna let y’all guess if I really work naked…) Good thing my life is casual and jeans with a nice tee shirt or cotton blouse works just about everywhere I go…except events in New Orleans.

I think I better start the process all over again for the cruise next spring. I have seven months to start buying and exchanging dresses. That should be enough time and I’ll be whipped in a frenzy of indecision well before I have to pack a bag and just take everything like I did this summer.

Any ideas for making this process of dressing to bridge the gap between matronly and trashy would be appreciated.