
I actually wrote this post for another blog almost a year ago. For some reason that blogger never published it on her site, so I’m going to put it here. It’s very different from my usual posts, so I hope you enjoy it. I was reminded of this after reading Michelle’s post on striking a balance between dressing too young and too old. And my apologies to the blogger for whom this was intended. If you ever decide to publish this on your site I’ll be happy to remove it from mine.
I’ve been into vintage clothing for a very long time, and at 57 I got to wear a lot of the styles that are vintage favorites today back when they were the height of fashion. When I discovered vintage clothing in the late 1970s, the vintage “industry” was quite new. Wearing vintage was not the popular clothing option it is today. I was discovering lovely pieces of old clothing but I didn’t want to look like it was Halloween. So instead of wearing a complete vintage outfit, I began incorporating vintage pieces into my modern wardrobe. This is a system that I’ve continued to use throughout the years.
For young women today, wearing vintage clothing is a fun alternative to modern clothing. But we older women sometimes are hesitant to go all out in a vintage ensemble. Often fit is an issue with a middle-aged figure, and many times the best vintage styles are simply too young looking.
There’s an old adage that says if you wore a fashion the first time it was popular, then your time is over. When it comes to vintage the “rule” might be that it is really hard to pull off a look that you remember wearing in years past. I’m not so sure one has to always adhere to such a rule, especially when it comes to classic pieces, but the truth is that an older person who wears something that dates to her adult lifetime runs the risk of looking like she raided the back of her own closet. This is not the image most of us want to put out there. Vintage is fun, but looking like you have not been shopping in 30 years is anything but.
So instead of revisiting the 1980s, go back further in time, to the early 1960s perhaps. I remember these clothes on the women in my childhood, but I was too young for the Jackie Kennedy look. Maybe that is why I find the clothing from the early 60s to be especially appealing.
That’s me in the photo, circa 1985. Clearly, my time for puffed sleeved sweaters has come and gone.

Forget looking for vintage that would be “age appropriate.” By that I mean don’t try to wear things a 55-year-old woman would have worn in 1965. Do you remember Aunt Bee from the Andy Griffith Show? That’s how middle-aged women were expected to look, but you should be going for pretty or sophisticated – anything but dowdy. A 25-year-old woman might be able to pull off your grandmother’s 1970 poly dress with the elastic waist, but you will just look like your grandmother.
Photo copyright CBS Paramount Television

Look for things that fit in with your sense of style. If you love plaids or stripes or blue or floral prints, use that love as a starting point in looking at vintage clothing. Buy things you would be comfortable wearing if they were new. One of the advantages of being older is that we generally know what we like and what suits us. I’m not saying to not be adventurous; I’m saying if it feels like someone else’s clothes you are not as likely to wear it.
I may not want to wear a 1980s puffed sleeve sweater, but this one from the 1940s fits my sense of style and love of the color blue.


Vintage dresses can be hard for the older woman to wear. Combine the fact that your waistline is likely a few inches larger than it was when you were 22 with the fact that until the late 1960s (and sometimes beyond) most women wore firm body shapers. You will probably find that most vintage dress shapes between 1930 and the mid 1960s are just too small in the waist.
If this is your concern, you might try these two dresses from the mid 1960s, the shirtdress and the shift. Contrary to common belief, not everyone in 1966 was running around in super-short minis. That was a few years later.

Look for clothing that was meant to have an easier fit like coats, jackets and sweaters. Because they were designed to wear over other garments, the fit is not as precise as a dress or a slim skirt. Most of the vintage I own that I actually wear is outerwear purely because it is easy to find things that fit.
Again, be careful regarding style. You want to find the right balance between too young and too dowdy. Many vintage coats were cut to fit over the big skirts of the 1950s and early 1960s, and these tend to look shapeless without something beneath to fill them out. An a-line coat like my Pendleton above is flattering for many body shapes.

If you are not sure about vintage clothing, start out with an accessory. The selection of vintage handbags is simply staggering, and the quality is often much better than in handbags available today. Evening bags are an exceptionally good buy, along with vintage bags in shapes that designers still turn to today.
If you love scarves, they are another great vintage value, not only silk ones but also cashmere and fine wool. Other accessories to consider are jewelry, belts, hats and even shoes.
I’d love to hear your tips for wearing vintage, regardless of your age.
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