When I was 21, I wore stilettos all day. I ran in black suede, three-inch heels to the bus stop, strode to the newspaper office where I worked and then spent half the day pounding the streets looking for stories.
When I was 23, I wore white leather stilettos for my wedding under my long white gown. My father led me down the aisle in them, I danced the night away in them, and never once complained that my feet hurt.
When do we reach the point where comfort outweighs fashion? Why don’t you see ladies in their 80s teetering around in pointy shoes? Why do older men opt for elastic-wa-sted pants and sneakers instead of tight jeans and leather shoes? Is it that we simply don’t care what we look like as we age or is the realization that it’s not how you look, but how you feel; the optimum feeling being comfort.
When I go shopping for shoes, whatever I’m looking for falls into two categories: 1) the beautiful styles I’d choose to display in a cabinet at home; and 2) the flat ugly monstrosities I’m not only prepared to try but will probably buy.
Try as I may to stick my head in the sand (thus avoiding the horror of trying to find a hat), I was recently forced to look at the truth. Despite the pandemic, our son had a co-starring role in a stunning English wedding. Although Mother of the Groom may not be as meaty a role as Mother of the Bride, I was still a featured player.

Initially, I resisted running (in my cotton sneakers) to the stores to look for a gown because with coronavirus still rampant, I thought the date might be postponed. But when things started looking up, I had to look down at the avalanche I laughingly call my figure and work out how to contain it for public viewing.
When I was younger, my friends and I constantly worried about what size clothes we wore, although, ironically, we never divulged it to each other. Over the years I’ve gone up and down so many times I feel like I’m trapped in an elevator.
More Top Picks Best Ge Refrigerators
I’ve been battling the side effects of COVID-19 for well over a year. By side effects I mean the amount of weight you can put on even when wearing a mask 90% of the time. Eventually I could put off the dress hunt no longer so I’ve ended up larger than I’d like but smaller than I was when my daughter got married seven years ago.
If I was a mother of the groom when I was 20, it would have been so much better, even if medically impossible. I could have worn anything I liked and looked stunning (especially if we’d have had the mask mandate in place then). But since Robin has taken his time to find Mrs. Right, I now find myself dealing with trying to spruce myself up while being no spring chicken, but mindful not to look like mutton dressed as lamb.
Henry Ford famously said: “You can have any color you want as long as it’s black.” I told my family I could have any color I wanted as long as it came with sleeves. Whatever size you are, as you age your arms deteriorate. Just when I thought my bingo wings couldn’t look worse, they developed wrinkles.
In case you’re wondering, a suggestion from Grumpy that I exercise more/at all was met with a withering look. This from the man who asked in the next breath if they made Spanx for men.
I did eventually find a dress so beautiful that I hoped the other guests would be so amazed by it that they wouldn’t notice who was inside. If they peeked, they’d see a short, middle-aged woman (assuming I live to 128) teetering on three-inch heels while trying to breathe in a pair of nylon granny panties with an upstairs balcony. I was politely told by the shop assistant that I should keep the cups inside the dress even with a bra because it would show my breasts where they were supposed to be. I think she made a fair point given their natural inclination to sit on my lap.
What worries me is why vanity is still an issue. If I was that concerned, surely, I’d eat Botox for breakfast and run 20 miles a day (in Orthoshoes). Does anyone really care how I look? They’ll only look better standing next to me.
Maybe the problem is I’m just not quite old enough. Perhaps people in their weighty 80s or naughty 90s have learned that comfort is king. If you’re struggling with the aches and pains that catch up with us all in the end, why expose yourself more anxiety by trying to squeeze your foot into an unnatural position? They say with age comes wisdom, so I can only assume this is one of things to which they’re referring.
For now I’ll refuse to wear sleeveless dresses on 100 degree days and stick with my flat, frumpy shoes. I’ll choose stretchy waistbands over zippers and rejoice when I find a hidden pocket in my pants. I still won’t make a run (in my Skechers) for the mailbox without make-up, but I’ll only wear Spanx in the winter to prevent me from catching hypothermia.
If I have learned one thing as I get older, it’s the battle for the ages is troublesome, but it’s better than the alternative.
Hilary Decent is a freelance journalist who moved from England to Naperville in 2007.