I hear you on the jeans. I meant Westminster, MD. I live in PA. I do have to wear proper dress clothing in my work environment (I sit on two boards). It's not so much the effort because I can be fully dressed in 10 minutes. I just like to look razor sharp at meetings. Starch white shirts and collars with undershirt, silk tie, suspenders (I like suspenders precisely because most men can't pull them off), tailored pants and jacket, sock garters (yes, I still use them), designer shoes, and watch. I always wear a watch. Even if I hardly use it. I like Breitling and Rolex. Men will notice your watch and women will notice your shoes. But most of all, since I know eyes are going to be on me, I like walking out the door feeling like a million bucks.
Jeans are always a pain because I have to buy 36in+ waist jeans to fit my legs. A tailor can take in the waist of those as well. But I probably haven't worn jeans in 10 years. Mostly just khaki or khaki green pants.
Reminds me of a conversation my brother and I had. He had told me he got a raise which put him over $100k (this was many years ago) and I asked him what he's going to do with all that money. He said, "As God as my witness, I'll never wear denim again." (from the old movie Gone with the Wind, "As God as my witness, I'll never go hungry again.")
We still laugh about it.