Style & Substance – My Midlife Stylish Phase and the Dignity of Aging Gracefully

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

Style & Substance – Knock Your Socks Off – A Modest Endorsement for Colorful & Patterned Socks


There is something to be said about the contemporary gentleman that grants thoughtful attention to his appearance, or at the bare minimum, conveys the impression that he gives a subtle damn about it. Generally speaking, a man will direct his focus on garments that are decidedly most visible: shirt/sweater, pants, and footwear. Simple. A gentleman’s socks, on the other hand, are quite the distant afterthought. Your hosiery deserves a lot better; don’t you agree? Your standard collection of solid blue, brown, and black socks are rightly exhausted, and a gentle refresh is definitely in order. As we have transitioned into spring with summer steadily on the horizon, a gentleman’s options are plentiful with colorful & patterned socks in stock and at the ready for purchase.

So, why should a gentleman elect to employ the services of a pair of seemingly garish hosiery about the ankles? Short and sweet answer: personality. You can quietly, smartly distinguish yourself from the homogenous masses. Allow me to recount a true story for the audience. One day, I was walking around a local mall on my lunchbreak, and I crossed paths with a former colleague from many years ago. After exchanging pleasantries and inquiring about one another’s families, she playfully commanded me to show her my socks. Sheepishly I raised the hem of a pants leg to reveal my sock selection for the day. I do not remember what I was wearing, but I do remember that she nodded with approval and complimented me for staying stylish.

The sartorial exercise is not terribly difficult to execute. As a simple rule of thumb, especially when the occasion is informal, I attempt to not match my socks with my trousers. Instead, I coordinate my socks with a top, necktie, or pocket square. And on the occasion when that is not a possibility, I aim for a lighter hue to make by socks stand out from my pants. For example, if my pants are dark blue, I would then opt for a shade a touch brighter and mix in an interesting pattern to ensure a distinct difference in appearance. Especially for warmer seasons, I lean into whimsical motifs that may see flowers, bees, flamingos, or butterflies adorning my ankles. However, if that direction is a bit much, one can never go wrong with variegated stripes, polka dots, or a combination of the two.

Ultimately, the objective should be to infuse your presentation with a hint of personality and character that elevates your style above the monotonous, humdrum offering of dark and solid. And if the execution strays a bit off course, no worries, you are a gentleman willing to take sartorial risks. I am willing to bet that you hit the target more times than not. It all starts with opening your mind and starting the process. There are plenty of shopping destinations such as Target, Macy’s, T.J. Maxx, and DSW that are stocked with affordable options for a gentleman. You can experiment with what works with your outfits without breaking the bank. You need only worry about the compliments you receive from the public!