People with money, don't need to prove it to anyone by wearing expensive labels. I wear clothes that fit well, make me feel comfortable and look clean. I could care less who made them. Right now I am wearing plaid shorts and a polo from Old Navy.
The shorts are a bit loose, like I like them to be. Really fitted clothes on folks with some muscle look too obvious. Jeans are an issue. I used to wear Levis but they are no longer comfortable feeling to me, so I switched to Lucky Jeans. They can be dressed up or down as depending on the occasion. They are always comfortable on me.
I like organic fabrics best. Silk shirts are great for staying cool during hot weather. I prefer clothes that can be washed as opposed to being dry cleaned. I'll make an exception to this rule with dress slacks and suits. However, being retired, I find I rarely wear a suit anymore.