I ask myself that question all the time. The horrible thing is, I never thought I would. I have always had my mother there to, very happily, tell me that I was not dressing my age.
It used to be that I was dressing too maturely: "You can't go out wearing that tight black mini-skirt and a lacey tank top. You are only fourteen! Do you want the boys to think you're easy?" Well . . . Yeah! Duh! But she would never buy that and she would follow me around 'til I changed.
A few years ago, shortly after my divorce it went like this: "Are you sure you want to go to your son's school play dressed in that black mini-skirt and lacey tank top?What do you think you are 20?" Well . . . Yeah! Duh! But she would never buy that and her voice would haunt me 'til I changed. Who ever said that dressing immaturely would be a problem? I live by my father's adage: "Dress young and act immature and no one will ever know how old you are."
My mother, maddeningly, was often right in her assessments. I can see that in hindsight.
Now I don't even need her. (Though she still will willingly offer her insight, if I ask her.) Every time I go out to buy a new outfit, I hear this voice say: "So are you really going to buy that? How pathetic are you? Do you think that will make you look even 25 again?" The voice (far harsher than my mother's) gets louder the more excited I am about my new look.
I believe my fashion barometer is slightly off because I work with a group of totally fashion conscious 17 year-old girls. My living example of "looking good" is what I see on these girls. I don't want to dress like a 17 year old, but a lot of the things they wear, I find very appealing.
Combine that with a total natural love of hip huggers and rayon and soft flowy fabrics and hippy things and I become a schizophrenic fashion disaster waiting to happen. The other day I got up (very early in the morning, thinking strictly of comfort to get me through the day) picked out a pair of black jeans; a purple, sort of tie-dyed long sleeved knit shirt; and a black, flowing sweater coat. I thought, in my half-groggy state, that I would pull it together with this green crocheted head band by scrunci.
I pulled it together alright. I pulled it all the way back to 1968. Then to top it off I had to go to an important meeting in the afternoon that I was not thinking about at 5 a.m. when I was dressing myself. Thankfully, most of the people in the meeting knew me, so my credibility was not absolutely lost.
But, 
my natural need for that hippy, artsy, creative look makes me wonder if I am turning into one of those middle aged hippy chicks that populate the arts community. They are very fine, down to earth, lovable women, and I would choose them over some other kinds of women every moment of the day, but I don't want to get pegged in that hole. Think Dharma's mom, Abby, on Dharma and Greg.
But, you know, that is not a bad stereotype to be put in, either. Maybe I have to just give in.
I have to start reading Brenda Kinsel again and get back in touch with where I want my image to head.
OH . . . Why won't the Fairy Stylist-Mother come wave her wand over my closet and give me clothes I look hot and impressive in, that are suitable for any occasion, and don't make me wonder what message I am sending to the world? That would be the best thing for me.
Anyway, I went looking around to see if others are having this trouble with being age appropriate. Kim Johnson Gross of More.com had this to say:
Our generation is redefining the concept of aging, just as we've redefined everything else. Style after 40 is not about competing with your daughters or dressing like the girl you were 20 years ago; it's about dressing like the girl you are now. If you prefer a scoop neck or a short skirt, how much of you you show is your decision. What really matters is that you feel as comfortable in your clothes as you do in your skin.
I like that conclusion. I forget that point a lot of the time. So many times I am fighting against this imaginary 25 year old that will steal everything I have if I am not vigilant. I am so afraid that my Honey, who fully knows how old I am and chose me over all the 25 year olds out there, will figure out that I am not 25, come to his senses and this wonderful life we have built will be gone. Where does that come from?
(Oh yeah! TV, Movies, the Internet . . . magazines, novels, the Bible. I need to make a note to myself to stay away from those things.)
I need to start having confidence in myself. Most of the time I do. I have a mantra that I recite when I start to feel down, or try to talk myself out of my Remodeling program. (It is still on-going, just not at the same speed as during the summer. I'm a bit busy these days.) I'm beginning to be more comfortable in my own skin and with my own likes and dislikes. I just have to learn to trust them and my instincts more.
I still have so many years of overcoming my Mother's voice to combat, and a lot of clothes she gave me with the assurances that they were far more appropriate than my tastes. (Remember she is very often quite right.)
Still I take heart in this quote from Kim Johnson Gross' piece:
The style-confident women I know say that the idea of age-appropriate dressing has no meaning for them; it's more about body-appropriate dressing. My friend Susan, an independent, creative mother of four, recently did a major purge of the dowdy clothes in her closet, most of which her mother had given her. "I kept them for years, thinking I would wear them when I turned 50," she says. "But 50 came and went, and I realized they still look dowdy -- and I don't."
