Girly Swirly Skirts and Dresses

It all started with my Betty Draper goes to Hawaii dress, and the swishy feeling of the dress on my calves, and the belted, cinched waist of the dress.  The next week I wore the dress (sans headscarf) to the banquet of a conference.  When I walked in I wondered if I should have worn something else, as almost everyone else - men and women alike - was wearing black.  My anxiety was soon allayed when other delegates (who were strangers to me) complemented me on the dress.  
 Why don't I own more dresses like this? I thought to myself.  The more I thought about it, the more I realized that what I liked about the dress, and why it looked good on me, was the a-line shape to it.  I have a small waist, and large hips and legs and such a style in skirts and dresses plays up my best feature (waist) and plays down my worst (lower half).  
At the same time, I stumbled upon a whole host of bloggers that are devoted to recreating (and wearing!) classic mid-century style - of which a-line skirts and dresses were standards.  More than that, they celebrate the art of dressing up and being proud of looking polished and glamorous.  Hopefully this is the start of a new movement, or maybe it is already a movement and I'm behind the times!  My newest blog discovery, Bringing Back Pretty, which is about, well, bringing back her pretty, opens with a classic quote from Coco Chanel, "I don't understand how a woman can leave the house without fixing herself up a little. If only out of politeness. And then, you never know, maybe thats the day she has a date with destiny. And it's best to be as pretty as possible for destiny."  My own sister at Carpe Diem Vintage wrote "I can just barely remember when I was a young girl that society was still polite and helpful. Men and women still dressed up to go shopping and had an air of style and class.....I really wanted to bring some glamour to my life. To do this I realized that we no longer have true glamour in the modern world - it has been lost to reality tv, rudeness, mega corporations, advertising and just plain stupidity. To recapture glamour, class and style I have to go back to another era."

Have a look at classy ladies and their wonderful vintage clothing and style at any of these blogs...Temperamental Broad,The Mysterious Life of the Metropolitan Housewife, Sassy Lassies Vintage Life, Yesterday Girl, Diary of a Vintage Girl, and Welcome to DeluxeVille.  So over the last week I have been taking a cue from these ladies by wearing my red lipstick, and dressing up in a-line and circle skirts while shopping, at work, and even walking the dog!  I am a bit of a clotheshorse and have some really nice clothes, but probably like a lot of people, I have this 'save' mentality, i.e. I have to save nice clothing for special occasions.  Well, I am going to try to break out of this mindset; I have the clothing so I might as well wear it.

 In my recent rummaging, I bought a vintage skirt at the Salvation Army.  It is probably from the 1980s, made in Canada, but it looks very much like it could have been from the 1950s/1960s....(apologies for the photo, I am alone and my only full-length mirror is in my closet)....

It is a shiny grey material and is very well-constructed, with pockets!  I love clothing with pockets as I have to carry around keys at work.  It is a size eight and fits like one - there was no vanity sizing in the 1980s!  I bought it in a bag sale for $6, and I paired it with a belt I purchased at my last bag sale there.  I think this skirt will be very versatile.  
Next to this skirt hung another one that I'm not so sure about, but I threw it into the bag anyway since I still had room.  
Please help me make a decision whether I should bother getting it drycleaned or not!  In some ways I love it, but it might be hideous!  I love it because of the polka dots and the cinched waist.  It also reminds me of all the European clothing (i.e. Steilmann) I was exposed to while working at a high-end boutique when I was in college in the early 90s -  and I'm sure it is from that time period...what do you think?

Is it too outdated?  Please be honest.