I lied. It is not my middle-age clothing crisis because my husband has informed me that after the age of 50 a person is officially OLD AGED. He’s a big help. I have trouble with remembering that I truly am no longer 28 because  in my head I still think the same. I feel the same. But when I put on certain clothes that have been hanging in my closet for decades that I just can’t seem to get rid of, I clearly see that I am no longer 28.

Don’t get me wrong, I actually would not go back to that age if you paid me. As most older, or should I say “mature” women have learned, the things we know now, the wisdom we have gained gives most of us such a greater appreciation and enjoyment of life. Yes, we have gone through it all. And we survived, and we will keep surviving, and enjoy every minute. We have transitioned through jobs until we have found our passions. We have gone through relationships, or worked through things in relationships until we have found true peace and love. We have supported friends and family through hard times, and celebrated the good times. We are thankful and authentic. We have it all. But when it is time to get dressed to go somewhere…..well, I can only speak for myself…I am lost.

Yes, I am lost somewhere between what is appropriate, what is comfortable and what is stylish. I wish I did not care at all about clothes, but I do. One of my greatest joys is shopping with my old college roommate and best friend Marion. We have lunch (accompanied by a bit of wine) and then we walk around a beautiful outdoor mall in Connecticut and stop in our favorite stores. We try on all kinds of things, we talk each other into buying things and sometimes out of buying things. Marion tends to grab cozy sweaters, the same earth colors…(“don’t you have that?” I might say, just to save her money…). And I tend to grab the same things, too. Black shirts. Because I thought I looked good in black back then in my 20’s. Why can’t I let go of that?  And I am always searching for the perfect jeans. I have one pair I love, they are so stretchy, you can slip them on without unzipping them. And no, they are not jeggings. Theoretically, jeggings sounds like a genius invention. But I tried them on, and no, they are not. They are weird (at least on me). Although I do like style, I am also rebellious against style and fashion making fools out of us women (no offense against my friends who love those expensive pocketbooks with the letter C on them, but spending more than 100 dollars on a pocket book makes me wonder….why???). Maybe I am a hypocrite because I might spend more than 100 dollars on boots that I love and that are so comfortable I might wear them for 3 years straight (and I have).

I have thought about the phases I have gone through with clothing. It goes way back to my first memory of what I was wearing at a significant event. I was probably 2 or 3, or whatever the age is when you get your first tricycle but are not yet completely potty trained. I was sitting on that little bike with black stretch pants and a red sweater that was itchy. It was sunny out, and I was sitting there thinking “I need to pee”. But I really did not feel like walking inside the house and up the stairs to where the bathroom was. So I decided to just sit there, on my little bike and pee. Not a good idea as those black stretch pants became very hot and uncomfortable when they were wet. And that was the end of my memory, but I do remember the outfit.

My next memory was elementary school and the smocked dresses we wore. I loved them. But I was obsessed with the elastic hair clips my best friend Terry Gnazzo wore in her long straight brown hair. I thought she was very cool because she could do a split and a back walkover, a cartwheel and handspring….. and her elastics were interesting.

Junior High was boring because I attended Our Lady of Mercy and wore the uniform: a plaid skirt, white blouse, and saddle shoes. The shoes were cool. High School was in the 70’s and most girls wore bell bottoms and mini skirts. I mostly wore dresses because my butt was bigger then, and did not fit well into those hip huggers… I also was chestier and very very modest and shy, so pretty much wore whatever covered my body. When I got to college, I wore the same thing almost every day. These Tee shirts with pockets were the cool thing to wear, with jeans. I had wranglers. Then Levis. I loved my levis. I tried to find them over the years but there were so many styles, different number connotations that I just did not have the patience to figure it out. 501’s?? 401’s??? ugh, too confusing.

But the best outfit of all was the overalls. In 1976 that was what we lived in. We still had the blue tee shirt, but we also had overalls. We wore them together and we never cared about wearing the same thing every day. I remember feeling comfortable.

Then, there was the disco era. I got me a pair of designer jeans (a cheap version, but I loved them). Crop tops became the style and spandex dresses were the big thing. When I look at pictures of myself back then, I think Jersey Shore. Oh, yes, I did have leopard print shirts. Now, I hate leopard print anything.

When I had my children, thank goodness leggings and oversize sweaters were in style because I lived in them….until I went back to work and transitioned to what I call the Anne Taylor’ed look. I bought from the sale rack at that store and created the perfect professional wardrobe much of which I still own (those Anne Taylor clothes really hold up!). I have actually removed some of the shoulder pads in the blazers and may still wear them….with jeans.

So then I blinked my eyes and I was 40. I blinked again and I was 50. Then I blinked and now I am 60. And I don’t know what to wear.

I have decided on a few things:

1. Whatever I wear, I need to be comfortable.
2. Whatever I wear, I need to be me.
3. Whatever I wear, I do not want attention (unless it is a holiday and I need to entertain kids).
4. Whatever I wear, it will not cost more than my mortgage.

I do love seeing the way some women dress and put things together that just look so pretty. Or maybe they look chill. Or classy. Or uniquely them. That is what I want. To look like me, which sometimes feels very confusing. I sometimes like to feel like I am wearing something pretty, like I felt when I tried on that muted purple flowing dress in the picture above. But that dress also felt like pajamas. And it was cheap. And when you spin your arms around the sleeves flow in the air an it is really cool. Simple pleasures. But sometimes, I just want my “happy clothes”. My friend Marion knows what that means. We both bought baggie comfy jean shorts that we wear almost daily in the warm months. We have a knit sweater with a hood that we also both bought and it was not on sale but we knew it was a happy sweater and so it is and probably will always be our favorite. But then sometimes, when my husband and I go out on a “date”, I want to look like a woman who is trying to impress her date. But still be comfortable and still be herself. So that is why I like to buy those cute shirts and jackets and jeans that are not jeggings but still look good. But then I need to remember my age. No, I am not 20 or 30 or 40 0r even 50. I am 60 and I don’t want to look like someone who is trying to be young again. But then again……should I really think about any of that? So what if I love to wear black shirts and my favorite boots, or Levi jeans or even leopard shirts?

So I ask you, how do you figure out what to wear? Is it a struggle like it is for me sometimes? Do you care about what others think, or do you pick what feels good to you? I think it is ok to want to look whatever way you want to look. If you want to look fancy, then dress fancy. If you want to look down to earth, because you are down to earth, then follow your heart. If you honestly have no time or interest at all in fashion or style or any of it, and just grab what is clean and comfortable, then all the power to you. I, personally, am stuck in the middle. I love learning about people through their self expression of what they wear. I had a good friend years ago named Eileen. She was a brilliant woman with three children the same age as my kids. When I first met her at the town pool club, I judged her by her appearance (I am embarrassed to admit). She had a leopard bathing suit on with matching earrings. She always wore lots of bangles and southwestern jewelry, turquoise stones hanging from silver chains. When I finally got to know her, she became my best friend because she had a heart of gold, and we were both the same kind of mothers. Our kids were everything to us. She told me she thought she was a native American Indian in her past life because they decorated themselves, and she loved to do that too. Since then, I always looked at jewelry in that way, as a way some people decorate themselves, and it does not mean they are vain, or shallow but only that jewelry connects them with something we may just not be able to relate to.

So where do I go from here? Well, I discovered some bell bottom leggings…..to me, the best of both worlds, comfort and style. I can wear them to work, yet they feel like pajamas. I also bought me some long Hippie shirts….they are totally me, but I think they are meant for younger women. But if I throw on that Happy Sweater, I don’t think that outfit will draw attention, and that is my only fear…..but should it be? Being an “older” woman, wearing a spandex leopard dress with saddle shoes and cool hair clips…and overalls, now that may draw attention. But comfy black leggings with a colorful long hippie shirt….now I say, that could be considered appropriate at any age.

I think it may take me awhile to figure it out. But for now, it will be a fusion of all of it. Maybe some black shirts, maybe some Levis if I ever find the right ones. Definitely legging bell bottoms and hippie shirts. For sure there will be happy sweaters and happy shorts. I can already picture me when I am 80 with my baggie jean shorts, cotton knit sweater with a hood and pockets and my white hair tied up in a cool elastic. Tomorrow I plan to get rid of some stuff. Gone will be the tight shirts, the crop tops, the short shorts, the professional blazers and suit pants I really never want to wear again. I need to make room for more happy clothes.

And if I figure out how to fuse happy clothes with style, I will definitely let you know.