If I was so rich I didn't have to work my life still wouldn't change all that much. The one thing I would do is get custom-made pants.
It's all well and good that most clothes are relatively cheap, and there are many of them because they are machine made, but damn if I can find pants that fit. And I've never met a guy whose pants fit perfectly.
One of my friends complains all the time he cannot find pants that fit. I've got around the problem by taking all my pants to a tailor and having them fitted. Which is kind of deflating that I have to buy pants and then pay again so they fit me.
At least I'm not like Hank Hill, who had to go to a support group because he didn't have a butt and had to sit on a pillow all the time.
I have no problem with shirts or shoes, but pants? That's a different story.
The first time I read Richard McKenna's The Sand Pebbles I was stuck by the fact all the sailors had custom-fitted clothes because a Chinese tailor came on board and measured all of them, then made their clothes.
I always dress casually but well. I remember a girl in college who said to me, "You dress casually all the time but you do know how to dress."
My problems with pants has gotten so bad I know spend extra money to buy hemp pants. They're the only I have never had to tailor...and they last for a long time...several years.
I have found women never gave a damn about my Bulova watch (from the '50s and rebuilt once) or my car. But clothes and shoes? Yes.