In my over 42 year adult professional career in institutional and personal finance, 27 years have involved helping families with their financial journey. In my eyes, building a quality classic timeless wardrobe fits that journey hand in glove. During my 10 years as a professional clothing advisor previously, I recall Harold Powell telling me that his stores had a philosophy of narrow and deep versus the trendy department or fashion oriented stores (the box chains today) who had a philosophy of wide and shallow. In other words in a Harold’s store there were charcoal grey, medium grey, Navy, Olive and or tan suits predominately solid with some muted patterns in the suit section (as opposed to a broad array of colors at our competitors. This meant that one could get the brand one could afford and had, for him, the best fit and he could wear that suit for decades knowing that it would be perpetually “in style”. Financially this still makes a great deal of sense to me be that a suit, sport coat, trouser, shoe or tie (shirts and socks simply don’t have the same resiliency and a shorter life longevity ). My basic advice is to buy things that will last but prudently stay within one’s budget. Less is more. If one were to allocate 1% of one’s income to clothing (after one has $1,000 minimum emergency funds and ZERO!!!! debt on anything but a home PERIOD!!!!!!!!!!) then if all one can afford is one navy blazer and grey trouser for dress wear that’s just fine. That will suffice in 90% of circumstances. To do that math - say a guy has $70,000 disposable income with only a mortgage as a liability-spending $700 on a navy blazer, trouser, shoe, belt, shirt, and tie would be very reasonable. While there are a million iterations of this-It’s the concept I am trying to get across: Buy the best classic timeless dress outfit you can presently afford based upon your limits. Having preached this since the early 1980s here is how I do that. I shop sales. I will illustrate using today’s OOTD