A pair of black leather pants, paired with boots, a black shirt and a leopard print scarf.
photo by author

Have you ever longed for a clothing item for so many years it reached bucket list status, and then when you finally bought it, despite your best efforts it didn’t mesh with your wardrobe, your style or your life?

For me that happened. The item: leather pants.

Throughout the 1980s, you couldn’t tune in to any music video program without spotting a popular rock star wearing leather pants. In always thinking how sharp they looked, I admit I felt a little bit of pant envy. Unfortunately, I couldn’t justify the expense of getting a pair, given how a teenager’s part-time work at $2.35 per hour didn’t go very far, even back then.

Just the same, for me, leather pants remained an iconic symbol epitomizing ultimate coolness. However, at the same time, I had a hard time envisioning their potential uses in the wardrobe of an average guy like me who had no immediate plans for headlining sold out arena concerts.

In my early 20s, I embarked upon my office career, focusing my limited resources on investment pieces for my professional wardrobe. In doing so, the idea of leather pants seemed even farther out of reach, which only served to help them attain an even higher legendary status.

However, in my mid-30s, things changed. By that point, I had curated a comfortable wardrobe to meet my business and casual needs. With more discretionary cash, I could afford to experiment with new pieces. It was while perusing the newspaper for Boxing Day sales that I noticed an ad for a nearby leather goods store offering a special on leather pants at a very affordable price.

The back-and-forth in my mind was relentless. Would I wear them enough to warrant the expense? Would I look as cool as my 1980s pop idols or would they look out of place? More importantly, I wondered if there a question of age appropriateness at this stage of life.

Compounding to my indecision was the fact that I was single at the time, with no prospects, and I wasn’t really going out all that much. Just the same, given the great Boxing Day price, I decided to bite the bullet and go see what they had, just to satisfy my curiosity.

On Boxing Day morning, as I arrived at the store, it was as if it was meant to be. I immediately spotted the pile of pants on special, only to move closer and find a pair in my size at the top of the pile. It was a sign!

When I tried them on, I was impressed by how comfortable they felt, fitting well in all the right spots. Naturally, they were too long, as most pants tend to be, given that I have the legs of an elf, but the sales clerk offered me details of their alteration service to get them to the perfect length for me. At that affordable price, how could I not make this bucket list item come true, regardless of whether I had a specific time and place in mind to wear them?

The day that the pants were to be ready, the adrenaline was pumping with excitement at this new wardrobe item I would be able to enjoy from that day forward. When I brought them home, it was time for a mini-fashion show. My task was to find the right wardrobe pieces to pair with them to still have an edgy rock and roll look but for a non-rock and roll civilian like me.

I definitely had the right boots and belt to pair with them perfectly. It was the other half of the body that was a little tricky to stylize. I tried different combinations of shirts, jackets and sweaters to find a combination that worked. After a while, the puzzle pieces came together to create an outfit that reflected and complemented my artistic aspirations at the time.

Over the following year, I wore different combinations of those pieces to a couple of functions right up until the holidays. While I was always comfortable, I do admit to feeling self-conscious whenever I saw people’s eyes darting downward. It was as if they were looking at the pants without looking at the pants. The fact that hardly anyone said anything made me wonder if the pants were the elephant in the room.

At age 40, I developed a food intolerance which resulted in a drastic change in my diet, eliminating so many of the foods I enjoyed. With the weight loss that followed, I also lost a full pant size. When I put on the leather pants, they looked like a sack of potatoes on me as most of my pants did, but I didn’t dare donate them just yet. They were moved to the back of my wardrobe.

Ten years later, through a fairly stable diet enriched with more substitutions around my food intolerance, my diet found a new normal, as did my weight. When I returned to my original waist size, the leather pants fit again, but at age 50, would they make me look like I was trying too hard, like a mid-life crisis waiting to happen? To allow me time to ponder the question, the pants continued to hang around in my closet.

And here we are, another decade later, and whenever I stumble upon them while decluttering my closet, I still admire them for the look I wish I could carry off successfully.

It is regrettable because over the years I have not shied away from pops of colour, striking patterns and styles that might not have been popular with most guys. I wasn’t afraid to make a statement without worrying about what people would think.

Yet I remain baffled to this day as to why I was never able to make leather pants work. It certainly wasn’t for a lack of trying, but I guess that when it comes to bucket list items, nothing is guaranteed. Just because I wanted to wear them for so long doesn’t necessarily mean that I was meant to wear them especially since pop prince and rock god were never in my wheelhouse.

I can’t help thinking that since I don’t lead a life inspired by Keith Richards or Lenny Kravitz, I may have aged out of the leather pant cohort altogether. That being the case, after 25 years of trying, maybe it’s time to let go of this bucket list item.

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Sincere thanks for reading!
Have a great day,
André


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