Fashion after Fifty

I am not sure when it happened.

All of a sudden I am feeling a bit out of the loop fashion-wise. Well, that is not entirely true. It really wasn’t sudden.  As a child of the seventies, I have always been a bit out of it as far as style goes. Let’s face it, when I was in high school my main “uniform” was a pair of Levi’s, a flannel shirt and a pair of work boots.

My style was something like Donna'sPhoto credit:
My style was something like Donna’s
Photo credit:

In the summer I might swap out the jeans for a pair of cut-offs, but I rarely showed my legs, so it had to be VERY hot for that to happen! I was a late bloomer, so the hippie style of the sixties was really my thing.  The most feminine thing that I owned was an embroidered gauze top. Being stylish wasn’t one of the things that I worried about.  My biggest memory of clothes and shopping when I was that age was talking my father in to letting me actually buy my jeans at the local “County Seat” store rather than the overstock farm store that sold fake Levi’s with the orange tab cut off.  It was all about that orange tab!

When the disco craze started at the end of the decade, many of my contemporaries started to dress up a bit – ala “Saturday Night Fever”, wearing heels and polyester fabric.  I have to admit that I tried a few of these styles, but I was always a bit uncomfortable with all of that.  Being a part of the ‘disco sucks’ contingent, I stuck to my hippie attire until the advent of the Preppie faze, which started conveniently during my college years.

My deck shoes, button downs and fair isle sweaters served me well for most of my adult life; taking me from my first job at a local high school, straight on through.  I have been a classic dresser during times of slim fitness and when I have been overweight. There always seemed to be stores where you could find a good cable knit sweater or a pair of chinos. No sweat and no real thought involved.

When I returned to the workforce in my thirties, I started wearing suits and slacks, so that was no problem, either. My casual wardrobe started to dwindle, but again, the classics prevailed and my biggest challenge was what type of jean leg to choose.  I stuck with boot cut and felt (fairly) comfortable for several years.

My recent wake up came when we attended my husband’s company Christmas party.  It was held at a local Japanese steak house and was a casual evening.  I chose to wear (surprise!) a wool sweater and jeans – I dressed them up a bit with some sparkly flats. I topped it with my black pea-coat and a beautiful pashima that my kids had given me as a gift last Christmas. I asked my youngest, who is still home on break, how I looked before I left and she said “great”, so I thought I was all set.

My husband telecommutes, so he does not work in a typical office situation.  Although I have never met any of his coworkers, he speaks of them often, so I have pictured them all in my mind.  Imagine my surprise when we walked up to the bar and were confronted by about 20 young, hip-looking people waiting to be seated.  A cruel twist of fate – we are now the “old folks”.  Even my husband’s boss is in his mid-thirties.  Much to his credit, I do say that Jim fits right in.  Even if he is a bit greyer than the others, he doesn’t look out of place at all.

The first thing that I noticed, when I looked around, was that I was the ONLY woman there not wearing knee length leather boots. (Well not the only one…there was one other woman who was dressed in a flowy, sixities-type flowery number, so I guess we weren’t the OLDEST ones there) Now, I have seen these boots and have actually mentioned to one of my children that I might like a pair.  As a matter of fact, she rolled her eyes and said “Mom, you know you have to wear skinny jeans with them, don’t you?”

Raising three teenaged daughters has taught me that there are certain lines that mothers do not cross. The most important rule is that Moms do not shop in the same stores as their children – unless it is Old Navy.  Nothing is more horrifying than a mother wearing a pair of American Eagle jeans.  Gap is ok, but nobody want’s their mom to have the same pocket pattern as they do! When I was thinner and in my early forties, I have to tell you that jean shopping was a terrible chore.  When did the waistline lower itself to my hips?  And how do I avoid my middle, which is much less firm after three pregnancies and the natural loss of elasticity that comes from aging, hanging over the edges.

So the question remains….what, exactly is appropriate after fifty?  A few years ago I decided to bow to the fashion gods and I bought a pair of Ugg boots. I had to promise to wear them UNDER my jeans (although I have to admit that when I wear them to work because it is actually snowing, I do tuck my dress slacks into them – I know this is a huge faux pas, but sometimes you gotta do what you gotta do).

Sperry Love <3 Please note the modern color and styling (and the boot cut jeans)
Sperry Love ❤
Please note the modern color and styling (and the boot cut jeans)

I was pleasantly surprised when last year or the year before my beloved Sperry started producing new and hip shoes. Gap, Old Navy and Department stores will continue to sell classic clothing, and I guess I am not quite ready for a lap rug – just yet.

I do think that I might reward myself, after I lose a few more pounds, though. Rest assured that I am pretty sure that no amount of spandex can make me look appropriate for the public dressed in “jeggings” (although it does seem that whoever thought of a jean that fits like a stretchy legging MUST have been thinking of middle-aged women –  am I right?), but perhaps a pair of skinny jeans might find their way into my closet.

If that is the case then perhaps I can go shopping for a pair of these:

Photo Source: hope they come in 'Wide Calf"
Photo Source:
I hope they come in ‘Wide Calf”



9 thoughts on “Fashion after Fifty

  1. Oh, man! I thought I was reading my diary!
    I loved the whole jeans and flannel and straight long hair phase of high school, and the khakhis and a sweater of college. I have NEVER been in fashion, but that fact has only started to bother me in the past few years, as I realized that I am not only unfashionable, but also too old to get that way.
    And my 27 year old daughter looks fabulous in those boots and skinny jeans.

  2. I have lamented about this for years ( now in my mid 60’s) hardly ever get dressed up anymore & when I have to have a terrible time finding something to wear. I really am a dress person, especially in the warm weather. I used to shop at Northern Reflections alot because they carried classic styles for women of a certain age–then they closed all the US stores! mostly go to Kohl’s now.

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