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The original comment in this post strikes close to me and is something that I have given much thought. I had to conclude, for myself, that I do not care much what others think of how I dress. I have no restrictions as to how I dress for work. Socially, I could wear shorts and no shirt without raising suspicion in my part of the South. I could also just as easily wear Gap and the Banana Republic and only be guilty of being the “Old Guy” trying to look young. Since I am 40 years old and back in college, I could default to sneakers, jeans, and a hoodie without being out of place. I tried all of those in the two years after my divorce but none of those are me, nor do I feel comfortable in those clothes.

I wear what I wear because it feels and looks good on me. For a while, it was jeans, boots, and a polo. Last year I added chinos into the rotation followed by OCBDs, better trousers, and finally a few sport coats. Now, most days I wear boots or loafers, jeans, sports shirt, and a sport coat. I own two suits, one for weddings and another for funerals. But, suits aren’t practical for me. If they become necessary, I can change that.

Do I feel like I am better than anyone else? No. Do I sometimes think I am overdressed and “out of place”? I did for a while, but I finally reached that point in my life that I need to live for myself and not someone else. If others feel like I’m “dressing up” or putting on airs, that isn’t my problem.

What I wear now allows me to be comfortable while being able to do anything I want to do. If I need to meet with a client, I do not feel underdressed. If I need to roll up my sleeves and change a tire, I can. If I need to help a neighbor out chasing a cow, I have barn boots in the trunk of the car. I will probably never reach the levels of style most aspire to on this site, nor do I care to, because it does not suit me.

For once in my life, I am comfortable in my clothes.
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