To be sure, I am certainly not the same gentleman I was thirty years ago – at least not in the physical sense. My years of youthful virility are slowly disappearing in the rearview of my life. My body’s check engine light sporadically illuminates as mysterious aches and pains quietly arrive unannounced. My creaky joints are a touch stiffer, reflexes are a shade slower, and small regions in my beard are producing hues of eggshell white. And to add insult to emotional injury: My son just beat me in a game of H-O-R-S-E with three midrange jump shots with his eyes closed. The rascal peeked no doubt; he is no Michael Jordan. I digress; this brother is aging. Now, I can either go kicking and screaming, or I can accept the reality that Father Time comes for us all. I have determined that I will not be that older gentleman that is blind to the inevitable, stark reality: Father Time is undefeated.

That brings me to today’s post. A few months ago, my wife and I were invited to a birthday celebration. As I began to assemble my outfit, I thought about the type of crowd that would be in attendance. I figured guests would be around the same age as the birthday couple. Now, ten years may not seem like a huge differential as it pertains to age groups, but one would be amazed how much change can transpire within a decade. And for reference, I am North of 40 years old. Quick aside: During my high school years, one of my uncles considered himself the consummate playboy. He was a handsome gentleman with an abundance of charisma to spare. However, as he grew older, his advancing age did not match his youthful presentation. I love the guy, but as years passed, it was obvious he was attempting to prolong his glory years. Not me. I do not have the desire to be the 50-year-old gentleman that dresses like he is 30 years younger. The outfit may whisper young adult, but the vanishing hairline and gray beard screams, “Get off my lawn!”

Nevertheless, I am wise, and there is no reason to compete with men decades my junior. I realize that a gentleman can still present himself with grace and polish without the appearance of desperately clinging to days gone by. There are simply too many stylish options at a guy’s disposal to not look fantastic. So, what do I do? For a semi-formal occasion, I still lean into a trustworthy, dark navy suit anchored by a mature necktie, an elegant pocket square, and sharp-looking dress shoes. If navy is not an option, I would reach for a charcoal grey one. If I am feeling a little saucy, and I do not want to present as too stodgy, I will opt for a dress shirt with either an interesting pattern or unconventional color to make the look pop.

On this evening, I chose a blue/white dress shirt with a small repeating diamond print, complemented by the minimalist vibe of my conservatively striped dark navy necktie. The suit was dark navy. My shoes were black cap-toe oxfords. I rounded out the look with a fanciful flower lapel and topped off by a gentleman’s crown – in this case my Bailey. Side note: I have unapologetically embraced the exercise of wearing hats as a part of my ensemble. It should be an item in everyone older gent’s starter pack. With my now salt & pepper beard, I carry the look off well. Not pictured here, but I did decide to rock blue paisley socks. Nevertheless, my sartorial selections were rightly indicative of this stage in my life – intelligently grown-up with just enough playful interest to garner quiet respect. Call it my midlife stylish phase. When I looked at a picture from that night, I could not help but recognize how I have aged. But I look handsome and distinguished. And I am cool with that.

• Suit – Hart Schaffner Marx
• Shirt – Forsyth of Canada
• Necktie – Eidos
• Pocket Square – Burberry
• Flower Lapel – Hook + Albert
• Socks – Paul Stuart
• Shoes – Allen Edmonds
• Watch – Tissot
• Hat – Bailey