I used to be a blue-jeans-and-T-shirt guy 90% of the time. I lived in Madison, Wisconsin, and there, that was completely normal. If I had worn a tie there, it would have been for a very special occasion.
In Italy, I found that I was underdressed by comparison to other men of my age and condition. Lawyers wear clothing of a more formal nature than I, and manual laborers much less formal. In Venice, clothing styles represent the kind of mix you might expect where fishermen and delivery guys live in close proximity to plutocrats and wealthy travelers walk the same streets as those who arrived on a €40 flight from London. It took me longer than I wish to admit, to realize that clothing matters here in a way I hadn’t grasped. [I had been told, but did not listen.]
In practical terms, dressing well usually results in being given a level of deference that you won’t get in blue jeans. A lot of places are happy to have your money, but I find they are much happier having you at a table if you add prestige rather than diminishing it.
Once I set about upgrading my wardrobe, I began to have fun with it. As a child, buying a blazer with my mother set the stage for blazer avoidance for the years following. Now I have more than I have space for in two apartments. I have more than I need, but I can’t predict that I’ll stop. I keep telling myself that I’ll get rid of the less excellent ones, but I almost never do.
I do occasionally spend real money (for me) on clothes, but I still like to get a bargain. I’m not at all sensitive to brands, per se, and even less interested in ripping tags off new clothes. If it’s good looking, fits, and in good repair, that’s all I need. If the price of alterations added in doesn’t make too much of a difference, then there is wiggle room on the ‘fits’ requirement. The leather coat above cost something like €25, with another €30 to have the sleeves shortened. It’s one of my favorite things to wear.