On Accidentally Becoming Stylish Through An Old Pair Of Shoes

We all know how quickly styles can change. Some of us are slaves to fashion, and are always on top of the newest trends. Others find a personal style and tend to stick with it. Those who have been reading here for awhile have probably figured out which camp your humble author calls home. There is also an under-appreciated benefit to those of us who are far from the leading edge of things – if we sit still or otherwise do our own thing long enough, the styles will come back around to where we have been all along. I had this phenomenon proved to me once again recently. It involved a pair of shoes.

I am currently in the brief downtime between the weddings of two of my children. The first one went well, by the way. As for the second, I was discussing the Dad-Dress-Code with my son. I was all set on the color of suit his bride has chosen, but was told that there would be a requirement for brown shoes. That was when I remembered the pair in the back of my closet.

In the year of my graduation from a large suburban high school, I was voted the most conservative in my class. And it was true. This wasn’t so much about politics (though I had passed out campaign literature for Ronald Reagan when he challenged Gerald Ford in the 1976 Republican primary) it was also about my personal style.

When long hair was in for guys, mine was short. When the leisure suit was a thing, the suit I owned had a vest – I even had a pocket watch on a chain. I never owned painter’s pants or loud bell-bottoms, but stuck to more classic styles, at least so far as was possible in the 1970’s when (what I viewed as ) good taste was in short supply. And then there were the shoes.

In late middle school, my best friend Dan (who was both more conservative and more individualistic than I was) started wearing a pair of old-school black wing-tip shoes. I thought they were cool and worked on my mother to get me a pair too. Yes, these were the height of un-cool in the mid-70’s. I had not seen my father in a pair of those since the mid 60’s, and they tended to be favored by business men of upper middle age. But with Dan leading the way, I got up the courage to join him in this orgy of non-conformity.

To my eventual good fortune, Dan’s shoes, and therefore the ones I wanted, were Florsheim Imperials. My mother almost had a heart attack when she saw the price tag – I had no idea that a pair of shoes could cost $100. But she had to admit that they were top quality shoes, and her resistance dissolved when she got my father to pay for them. I wore them every day, in all kinds of weather, but they took everything I dished out and then some.

It was probably after I graduated high school that I got the brown ones. I worked in a job where I needed to wear a suit, and thought the brown ones might be a good second option. I can’t recall, but with a job and some money saved, I may have swallowed hard and bought these myself. The black ones were worn much more frequently, and by the early ’80s brown shoes had gone out of style so they didn’t get much use.

I wore them occasionally through the decades. That’s the nice thing about buying something without regard to style – when they are never really in style, they are never completely out of style either. But now I have discovered that these shoes have become some kinds of vintage classics. So “hello there, coolness – I have been waiting a long time, and now here you are.”

Florsheim Shoes was started in Chicago by Milton Florsheim in 1892. The family business maintained high quality standards for the shoes it made, and these high standards continued for quite a number of years, even after selling out to a larger company in 1953. Shoes in their Imperial line are evidently sought-after vintage items today, and there are some people doing refurbishments on them and selling them for not-insignificant sums (such as here).

My own pair seem to be the style 90632 Kenmoor. This style, made from 1958 to 1988, seems to be the quintessential Florsheim oxford, a really heavy pair of shoes that have picked up the nickname of”gunboats”. More than one source I have found calls these among the finest quality shoes ever made in the U.S. I will confess that I had not the slightest awareness of this when I picked them out.

It is rare that I end up with something collectible by accident, but here we are. I have to confess that the black pair suffered from heavy use earlier in their lives, and later became my “bad weather dress shoes”. But then these were evidently designed to withstand bad weather in the way they were so dramatically over-built. They will still polish up decently, but a close look reveals that they have not lived the easiest life. The brown ones, however, are in gorgeous condition, having only received one new pair of heels over the years (though not in the original style with the metal cleats all around the edge).

Not many of us can boast of owning a pair of shoes for 45 years, much less having those shoes be something that can be pulled out of the closet and put into service when the occasion calls for it – especially a demanding occasion like a family wedding. But as one who revels in the unusual, I am kind of loving being in this position. So after this little bit of research into current trends, I will be able to walk into my son’s wedding in a really old pair of shoes while holding my head high in the knowledge that for the first time in my life, my brown Florsheim wingtip shoes are actually (at least a little) cool.

Further reading on vintage Florsheim mens’ shoes can be found here or here. Lead photo by the author, others from examples as depicted on vcleat.com.

COAL Update: About how I came to own and enjoy what some argue is the best car that the Ford Motor Company ever built. This would have been a perfect pairing with last week’s foray into popular jazz music of the 1920’s, but we will just have to make do.


42 thoughts on “On Accidentally Becoming Stylish Through An Old Pair Of Shoes

  1. You know you’ve gotten to the point of buying quality goods, when they can be repaired multiple times to last long. In this case resolved and reheeled! One reason I bought Florsheim penny loafers with the leather sole instead of the non resoleable one! . Gotta say I love a good wingtip, but didn’t know that they were hip until the art Dept.. People back in the 90’s went Gaga for them! Weinberg being my brand.

    Liked by 1 person

    • You knew they were hip in the 90s, but look how far behind you I am – I just found out, what, 25 years later? Maybe the “hip cycle” moves faster than it used to and I am in the middle of a different one than you experienced.

      I agree – I am no screaming, Greta-loving eco-freak, but something like this that has an almost infinite lifetime with care and repair instead of being dumpster-fill after 3 years appeals to me a lot.


  2. You have now answered a long time question that started in my childhood – who bought Florsheim shoes?

    At the time you purchased these there was a Florsheim factory in Cape Girardeau, MO, and I traveled past it countless times on the way to my grandparent’s house. Always called simply “the shoe factory” my childhood brain never could compute having a shoe factory right in the backyard yet nobody I knew having any of that brand. It made no sense.

    Until one day.

    My mother, being a nurse, needed good quality shoes while roaming the halls of the orthopedic wing of nearby St. Francis Hospital. One day she ‘fessed up to my father saying she had bought a pair of Florsheim shoes. With the wind seemingly gone from his sails, he asked how much. That was my first real indication about Florsheim shoes. She likely still has those shoes. Sometime later she bought him a pair and I heard her mutter “he won’t say a thing if they are his”. Such is my parent’s relationship.

    Looking back I’m not sure if I’ve ever had a pair of Florsheim shoes or not. Either way, I have never heard a bad word about them and I suspect yours will still be in great condition 45 years from now.

    Liked by 1 person

    • That’s interesting – I knew that Florsheim’s main factory was in Chicago, but did not dig deep enough to see that they had one in Missouri too. And in another 45 years, those shoes will almost certainly be in better shape than me!


  3. I love a pair of excellent quality shoes. They matter a lot more to me since my slightly botched bunion surgery in 2014. I can’t wear just any old shoe anymore, and I find the better constructed they are, the happier my foot is.

    Liked by 1 person

    • As I have gotten older, I have tended away from “hard shoes” like these for most daily wear, but only for occasions that require a suit. And like you, cheap shoes that feel OK in a store don’t feel so great after a few months.


  4. Btw, those interested in shoes still made in America can buy Allen Edmonds from Wisconsin, but I recommend you bring your wheelbarrow of money! I have to say I almost bought a Pair once, but they didn’t seem to fit my feet right, and that’s a lot of money for stuff that might not fit right! Lots of sales to the C hinese and Japanese for them, and also made famous by the Clinton;Whitehouse. The Clinton years were also the time it became acceptable to ditch the patent leather with a tux and just wear cap toed Oxfords…


    Liked by 1 person

    • I learned my Florsheim lesson well, and some time in the early to mid 00s needed a new pair of black dress shoes. I swallowed hard and popped for a pair of Aldens. Alden is apparently the last shoe company that makes shoes in New England, and like the ones you note, they are not shy about charging for them. I am sure they cost a lot more now than they did when I got mine. But like with these Florsheims, I expect they will last me the rest of my life.


      • When I lived In DC, there was a men’s store that carried Alden shoes and they had a vintage line of reproduced styles from the 40’s and 50’s. Actually quite well made, quite beautiful, and quite expensive.

        Liked by 1 person

  5. That’s great, you have been blessed in the area of brown shoes. Remember that line from Spinal Tap, St. Hubbins is the parton saint of quality footwear!

    I have a pair of light brown wingtips, not Florsheim quality but the are the only shoes I’ve owned where random women say “hey, nice shoes”. I’ve had them about 10 or 15 years, the bottoms are paper thin now. I should really get them worked on, but where? Now that’s an idea for a future article..

    Liked by 1 person

    • I am fortunate to live in an area where there are still a few shoe repair places around. That would indeed make a good subject – I still remember the place my mom used to take us kids to drop off shoes for new soles and heels. I still remember the smell of leather and polish.


  6. I have a pair of dress shoes going back to the ’70s, from a time when you could get men’s shoes with a slightly thicker heel, thus elevating one’s height. These are not platform shoes, this was just the style then. I put them on maybe last year, and it felt really different to have them on. The toe is quite rounded on them.
    Florsheim shoes were always the best ones to buy, but more expensive for sure. I have had a couple of pairs over the years, sometimes buying them at Sears.
    A pair of western boots made their way into my ownership around 1982, and they are still with me. They are a bit too narrow to wear now, but I did use them some in that decade. Their heel is also a bit taller, but at 5’10”, additional height is not needed for me.
    Speaking of footwear, was roller skating ever a thing for you? I still have my pair, bought in 1973, last used in about 2017, and needing a workout.

    Liked by 1 person

    • The only roller skates I ever had were the metal sidewalk skates that clamped onto the sole of your shoes. Good grief, I have no idea what ever happened to them. I would be scared to death to try to skate along the concrete today – I doubt that it would end well.


  7. You were “Most Conservative”. In Jr. H.S., I was voted “Class Individualist”. I didn’t know what “individualist” meant. Now I know.

    I don’t wear jeans, I don’t wear sneakers, and I only wear button shirts w/ collars. These days I do the “untuckit” thing. My “messy job” shoes are former dress shoes that are worn out. I like shoes with the Vibram-type soles; I can’t wear hard sole dress shoes like those Imperials. I’m also a B width, which complicates things.

    As for uncool things that have now come back, the MOST surprising to me are those 1950s-60s-70s NERD glasses. I see news commentators on TV wearing them now. And the whole soyboy, hipster look–you know, with the beard, the dork glasses, and ending every sentence as if it’s A QUESTION? (like a girl). It’s slightly Victorian/lumberjack, but somehow almost feminine, vaguely beatnik, but definitely 2020s. I would have never predicted such a look would become popular.

    Liked by 1 person

    • You are right about the glasses – the ones popular now are the ones that were hopelessly dorky when I started wearing glasses in grade school, so I have avoided them ever since.

      I will wear jeans, but only with button down shirts or maybe polo shirts. But I am happiest in a pair of khakis with one of those long sleeve button-downs.


  8. Did you try them on… they still fit? I’ve found my foot has changed over the years and favorite shoes are either too loose, too short, too wide, etc. They just don’t fit the same. GOOD for YOU if they do. Beautiful shoes! I remember that brand well. SO — we want to hear how the wedding goes!

    Liked by 1 person

    • I was fortunate that when I got my first pair, I thought my feet might not be done growing, so I got them a little big. I was wrong. But they were comfy enough and I got the brown pair in the same size – so after a little age-based spreading, they still fit nicely.

      I am sure I will come up with a topic that will address my traffic jam of weddings.

      Liked by 1 person

  9. Your comment about new heels explains, perhaps, why shoe repair is still a business. I drove past one of them recently and thought, “who goes THERE in this day and age?” Shoes like yours deserve an extended life. I also thought it would’ve been “cool” to hang onto the noteworthy pairs of shoes I’ve had throughout my life. Wouldn’t be practical to store them or even fashionable to wear most of them, but my choices over time would’ve been fascinating to see.

    Liked by 1 person

    • It has been a long time since I used a shoe repair shop, and I had to look up to see if one was still around. I remember going in with one pair quite a few years ago, and the guy looked at them, shook his head, and said “I can’t do anything with these – they are not made to be repaired.”

      Liked by 1 person

  10. Congratulations on becoming hip! I remember Florsheim shoes – good quality but very expensive. While the shoes are nice, I hate that trend of brown shoes with a black suit – Trudeau popularized it here. Black shoes are just a more classic dressy look.

    Liked by 1 person

      • Marianne never had that desire – I just confirmed it with her yesterday that she never got into that rumble seat. But lots of people loved it, especially kids. It was a bit of a climb, with one step on the back bumper and another at the top of the rear fender. The cars that were built with them had a rear window that rolled down, but my converted car did not, so there was not much conversation between the inside people and the outside people.

        Liked by 1 person

      • I remember my dad, who was born in 1926, talking about going to church in his Uncle Charlie’s Model T. This would be in the early 30’s. The kids had to sit on the floor and it was a long and very uncomfortable ride. The parish back then was clustered with one an hour away, as they didn’t have enough priests for awhile. I have a photo of the car somewhere, I should look for it. Someone might have had a fedora….

        Liked by 1 person

    • Like you, I have never been much of a brown shoe guy when it comes to wearing suits (unless the suits are brown too, but those have not been very common). Which is why these have stayed so nice. At least the suit for this son’s wedding will be a medium dark blue.

      Liked by 1 person

      • JP and Joni…coming from the rag trade in advertising photography, I can say without malice that I was always taught that there are two colors of men’s accessories (I.e. shoes and belts), At least for dress, and that’s black and cordovan, cordovan being a burgundy color, but; historically was actually the ass muscles of a horse , highly wear tolerant, and processed to that dark reddish color, but probably just a color today. Of course, belt must match shoes. Suits were to be very subtle, and stay away from patterns, any dress novice can tell a cheap patterned suit by the fact that the pattern doesn’t match at the sleeve and torso.

        Of course, all an open option today. Reagan made wearing brown suits accepatable (although pretty ugly chocolate brown),and as long as your colors don’t clash, shoe colors are all over the place. I will. say, the saddest Thing I see is
        Always a very nicely dressed woman out with some rube wearing a wrinkled t shirt and pants in sweat materials. Sheesh, even I can throw on a white shirt and tie!

        Liked by 2 people

  11. My dress shoes have been very rarely worn since I retired 19 years ago, so they will never wear out. I never did wear wingtips and now I live in running shoes even when in a sport coat. You undoubtedly look good in your shoes but more importantly you feel good when you wear them. What better place than a wedding to look and feel good.

    Liked by 1 person

  12. JP, first of all, what is this trend with brown shoes with dark suits? I must be old-fashioned as I don’t care for it anymore than the tight-fitting dress suits. I saw some Homecoming dance pictures the other day online in the local paper – no shoes or sneakers, pants waiting for the floods for the guys. I sound like my mom who wondered aloud about teenage trends (not that I was allowed to wear outlandish clothes.)

    I can recall my mom saying to me many times “you only get what you pay for.” Florsheim brand shoes were classic shoes, made to last forever if you took care of them. I am positive that I wore that brand of pumps at one time. I can remember getting shoes re-soled over the years if they still looked good. The first law firm where I worked had a dress code – no pants for women, so well-fitting pumps were a necessity.

    When I think of wing-tips or brogues, whatever name you choose to call them, I immediately think of lawyers. The firm I mentioned above was ultra-conservative. It was all male attorneys when I began there and they daren’t run down to the cigar stand downstairs without wearing a suit jacket. They had to wear a vest at all times and never a sports jacket. Lastly, there must be brogues or don’t show up. I can recall like it was yesterday, a young associate who was flying to New York to compete in the NYC Marathon. He had gone to school at Colgate University so planned to get together with friends soon after flying into the City. It was a Friday morning and he had a simple motion hearing around the corner and ran in to drop off the file after the hearing. Unfortunately, the senior partner saw him make that quick dash from the front door to his office in a Harris Tweed jacket, a pale yellow shirt and tie and cowboy boots. I faced Jim’s office and saw his clothing and thought to myself “you’re taking a heckuva chance coming into the office dressed like that Jim.” Yes, the senior partner marched into his office and yelled so the whole office could hear about the dress code. Jim slunk out of his office quietly – he was not fired surprisingly, but it would not have surprised me if he was fired on the spot. In those days before e-filing of court documents, the law clerk, runner or lowest-man-on-the-totem-pole associate was often sent scurrying at the last minute to timely file a mediation summary, or motion … again, no matter if it was five minutes before the court closed, no excuse for deviating from those brogues. Hope they were made for their wearer to be fleet of foot as they didn’t appear to be.

    Liked by 1 person

  13. This was an interesting read JP. That’s great you have a pilot’s license … I didn’t know you could get a two-step license to fly a plane and yes, knowing the instrument panel and being certified would be to your advantage. 🙂 I went to a Model A display a few years ago and had a great time. The event centered around the 90th anniversary of Ford’s Model A. Just like you belonged to, there is a local Model A club here and many of the members were displaying their vehicles … some cars, trucks or a type of produce wagon. The owners were eager to let you peer inside and I stayed there a few hours chattin’ it up with the owners, partly because they were so friendly and partly because I decided it would make a fun blog post. I imagine your kids loved the rumble seat and the excitement of being in this classic car. I like seeing these cars on the road and have to admit that everyone stops and has a look and if the vehicle is parked, there is always a crowd clustered around and checking it out.

    I just looked to see if I sent you the link to this post in the past, like when I did the Classic Cruise perhaps and I did not, so I’ll send it in a separate comment in case the link causes this comment to go to SPAM.

    I didn’t know that “Ford’s Garage” was a restaurant chain; I thought this one was unique to Dearborn, home of FoMoCo. When I walk the Rouge Gateway Trail, the restaurant is across the street. I’ve never eaten there but looked online at the interior before and yes, you’re right, all car parts. In college, we used to go to a restaurant called “Henry’s Place” which was similarly decked out in miscellaneous Ford car parts. A restaurant in downtown Detroit called “Jim’s Garage” had actual seats (from later model classic cars circa the 50s) that were booths you sat in.


  14. Pingback: 2022 – Crossing The Finish Line | J. P.'s Blog

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