Middle-Aged Man and Dr. Martens: A Love-Hate Story

I first learned about Dr. Martens in 1992, when my friend Matt, who was cool as all get-out, was wearing a pair on campus at the small college I was attending in New Hampshire. The shoes were Docs, the 1460s, kind of shiny, and not the boots. When I got the chance, I had a pair of my own.
Wearing Docs fit in with my developing darker persona in the early-to-mid '90s. I wore mostly black, listened to the Sisters of Mercy, wore an old Army-Surplus field coat, and was pissed off at the world. Living in Boston, and living without a car, I walked everywhere. The city streets are rough on footwear, and my jobs always required a lot of time on my feet, so the Docs were great! --Once I had them broken in. As a teacher, I liked that they were tough and comfortable and fit well with my lifestyle as a young ESL teacher on the make (if an ESL teacher can ever be said to be "on the make").
Then I moved to Fiji, and Docs did not work in that environment at all. They quickly molded over and became unrecognizable in that hot and humid tropical environment. I ended up wearing cheap flip-flops a lot or Fiji-bought sandals. Docs just didn't fit in there.
Two years later, I was back home and thoroughly cleaned my Docs. Back again, but not angry anymore, my Docs still served me, but I branched out a lot: Rockports, Bostonians, Tevas, sneakers, and the Docs were not as prominent a thing, though I still had at least two pair at all times in my closet.
Next, I ended up in Hawaii, and for those five years, I did not wear my Docs as much at all. They didn't fit in so well there either. Plus, I was not happy with a pair I had bought to replace a dying pair. The new ones were cheaply made and didn't have the same quality feel I had been used to. I continued to branch out even more, but I still had some Docs.
Five years later, I land in North Carolina, and Docs don't fit in much there either because it is very rural and more suited to boots. My body was also changing. Who knew that could still happen? My feel had grown and all my shoes were too small for me. I had to ditch all my old shoes, including my Docs. When I bought new ones, the break-in was killing me! My feet also didn't like being in them all day long like they used to. My feet were getting too old for Docs!
I started riding a motorcycle, and I needed boots, not shoes, and the boot-version of the Docs didn't appeal to me at the time. I ended up getting Harley boots, which were uncomfortable to wear all day, and then I got Red Wing 608 boots. They were the solution! This was especially true since I had broken my right leg above the ankle one night coming home from work, wearing Sketchers.
Thus began the boot-wearing phase of my life. I need the ankle and shin support. My right leg has never been the same since the accident. Add to this the fact that my Oxford-style Docs went bad on me, the sole splitting. I figured that I would try one more time to see if Docs could be part of my life and got a pair of "For Life" 1460-style soft-leather boots. They were very comfortable, but I like shiny, not matte, and all my socks got sucked down into the boot as I walked, which was annoying, so I stayed with my Red Wings. I even branched out, getting some Carolina Lineman boots that wen to my knees, and some Chippewa Engineer boots that also went way up. I like the style, and I need the extra support. But being older, lazier, and in lots of pain all over, I could not contemplate getting a pair of Docs like I used to own. The break-in would suck, and what if they hurt my feet again?
Then, I saw some Docs online in the Made-in-England collection of Heritage Dr. Martens. They are called the "Arthur." I also got another pair of Red Wings, a bit nicer than the ones I already have. So now, I have a nicer pair of Red Wings in brown, which are very Carolina-appropriate, and I have a pair of shiny, new Docs, the boot-ish version, which I hope will be easier to break in. I also find myself with a desire to take the time and energy needed to lace up my boots, care for my boots, which is a far cry from where I have been the past few years. I have gotten lazy to the point of insanity. I wear slip-on Crocs, the beige or the gray canvass types, and I have a pair of cheap-ass slip-on penny loafers. Comfort and easy on/easy off have dominated my footwear. But I know that with the colder weather, I will need ankle support again. The leg pain will worsen.
So now I am wearing Dr. Martens again, hoping to make them my go-to shoe, the one I love most of all. I have missed my Docs of old, so it is nice to come back to them. I just hope that I don't suffer too much from their less comfortable aspects.
Which begs the question: Can middle-aged men wear Docs anymore? Will I end up like so many of the old guys I see out there: sporting big, goofy-looking marshmallow-puffy sneakers?? God, I hope not! I plan on heading off the pain by wearing cushiony socks, getting better insoles, wearing a blister-proof balm, resorting to Dr. Scholl's Mole Skins, rubbing the shoes with dubbins and balm to soften the leather, and hopefully, I will be OK.
I hate having sore feet!