I have written posts on this blog about wearing boots with suits. Over the years, I have received questions from men who had concerns that “a man does not wear boots with a suit!” Poppycock.

I have provided gentle counsel along the lines of “wear what suits you best.” Generally along the lines of “wear what you like; to heck with the opinion of some style queens or your mother. Be your own man!”

During my working career, I wore suits for important and high-level meetings with the Big Cheese and his direct reports. However, I admit, I never quite felt comfortable in a suit. To me, a suit felt confining and hot. I felt ill-at-ease, and that would show on my face.

After I retired at the end of 2019, I donated the suits I had to charity, and thought…

… “no more suits! Boots and jeans all the way!”

Then in July 2020, my husband contracted pancreatic cancer. What I wore when I was caring for him was a requirement of function, not fashion. (Boots & jeans when I had to take him to a medical appointment; scrubs & stocking feet at home.)

2021 was a “lost year” of grieving after my husband died in early January. I did a lot of renovation work on my house, and for that, I wore work boots & jeans.

However, in mid-2021, I had an important function that I had to attend. The event dress code for men was a suit. Yipes! I did not have a suit that fit me any more!

I high-tailed it to Brooks Brothers and got fitted for a traditional navy wool suit and had it altered to fit my current size. I appreciate that they worked with me to get me a good suit in time for the event I had to attend.

I realized when wearing that suit that I felt comfortable. Not hot. Not confined. Even the necktie on my dress shirt didn’t feel confining because Brooks Brothers took care of that too. They measured my neck and sleeve length and told me that my current dress shirts felt confining with a tie because my old shirts were too small.

Once I got a properly fitted dress shirt, it was like “wham! I’ve been doing this all wrong for years!” I could wear a tie and not have it feel like it was choking me. Who knew? Well, “stylists” knew, but I was too reluctant to listen.

It was also rather amusing that when I got that suit, I got over my reticence to wear dress shoes. Some of them caught my fancy and I started a dress shoe collection to complement the expansion of my wardrobe, now that I was properly educated (and more willing to listen.)

These days, I choose to wear a suit more often than I used to.

I kinda like how I look and how I feel. In fact, I have added a few more well-made suits to my wardrobe and wear them when I want to — not when “I have to.”

I choose good-looking dress boots (both short boots that sort of look like dress shoes as well as dress leather cowboy boots) to wear with my suits.

When I wear the suit with boots, no one — NO ONE — says a thing! I may also choose to wear dress shoes with the suits as well. Whatever tickles my fancy. Who cares? It only makes a difference perhaps if I were going on a job interview; but I am well beyond that.

I don’t care what other people think or may say. That feeling is one of maturity, but also just me being me. As my interests change with time, I choose to wear what fits me, what feels good, and what I like.

By the way: does this mean that I do not wear leather any more?

No! I wear leather during cool or cold weather around the house, my community as I go about daily business, and of course when I ride my Harley. Leather is comfortable also, and goes well with boots (of course) or even dress shoes. Again, who cares? Wear what best suits the occasion and your preferences.

I put together a dress leather suit from my leather gear I already had. It looks hot with a pair of dress shoes, too. I have not (yet) worn the leather suit to a dressy event, but who knows what the future will bring?

Life is short: suit up with boots or dress shoes — anything but flip-flops, sneakers, or crocs!