Grandma Jezebels in Mini-Skirts and Halter Tops

 "Too many women—and men—dress to look far younger than they are. In the summer months, Madison Avenue is littered with grandma Jezebels in miniskirts and halter-tops. Preposterous. I’m proud of my 54 years and I wouldn’t go backwards for anything. I know better than to wear muscle shirts and gym shorts and dress like a teenager. At the same time, I don’t want to look dowdy or frumpy. I dress for my age and my role in life. Last year, I covered red-carpet fashion at the Oscars for the “Today Show.” Who was the most stylish and sexiest? Helen Mirren, that’s who." -- Tim Gunn

One of the topics that is close to my heart is dressing appropriately for your age (or at least my dressing appropriately for my age).  Pretty much from birth through high school, my mother exerted considerable control over my wardrobe.  The majority of clothes that I owned were clothes that she purchased without any input from me at all.  As a result, I was the only 8th grader I knew who owned a three-piece, black polyester pantsuit.  I once asked my mother why she bought that for me, and she told me that she had wanted to get me something that made me feel grown up.  She could have gone with heels or pretty underwear, but no.  My mother had very specific ideas about what I should wear, and it usually boiled down to what she liked to wear which meant that until I was able to afford my own clothes, at least half of my wardrobe was more appropriate for a woman in her late 30s to early 40s.  Because of this, I had no personal style and no taste.

Color it black, and this was me.  I wore it once.  To school.  Everyone asked me who died.

I pay a lot more attention to fashion now, and while I'm not cutting edge by even the most liberal interpretation, I feel that most days, I look at least put together.  Now I find that I gravitate towards separates and dresses with a liberal sprinkling of denim thrown in.  Thanks to my step-dad whose sweaters I used to steal constantly, I've never met a cardigan that I didn't like. 

Here's my mom in a typical outfit a few Christmases ago.  She likes sets and things that match exactly.  Grown up Garanimals.

Thanks to a combination of my geriatric childhood wardrobe and my regular missteps in dressing myself that come from not really having figured myself out yet fashion-wise, I've kept things pretty safe.  I've managed to control some of my wilder fashion impulses like knee socks with skirts and dresses, miniskirts and ruffles (although I will admit to owning a purple, ruffled pleather satchel) because I suspect that they might not be cute on me as they look on the 18-year-old sales person at Anthropologie.  But lately, I've noticed a dissatisfaction with the items in my closet and a hesitation to wear things previously loved (like my biker boots with a floral dress and boot socks pulled up over the top.  No, seriously.  That was last year's Thanksgiving outfit).  I mean, that was my uniform in the early 90s, but should I still be wearing it?  It's been said to the point of cliché, but if you are old enough to have worn a trend the first time through, you're too old to wear it when it comes around again.

Look how cute that Mr. flyskim and I sort of match.  Too bad you can't see the boots, but this is the only picture I have of me from Thanksgiving.

So how do you tell if your closet needs to grow up?  I've been reading a lot on the subject, and the one thing I've been able to figure out is that the answer to this question is different for everybody.  It's not my goal to provide a bunch of rules so that everyone can dress in some version of what I think is appropriate (although if you are well into your 50s and get on the bus wearing a halter top and Daisy Dukes with your Uggs -- true story -- I will mentally judge you).  What I'd really like to figure out is who I am today clothes-wise.  At my real age.  Keep the parts that still work but let go of the things that don't.  And not be boring.  God, there are days when I feel so boring I can't believe that people don't fall asleep just looking at me.  

Anyone have a guide for that sort of thing?  I will think on this and let you know what I figure out.