Consumption cycle to help us spend more $

Wife and I are HENRYs who both grew up with basically nothing. We are finally in a place where we can afford some nicer purchases, but after so many years of frugality find the money hard to spend. Curious for tips and tricks to keeping up with fashion or buying nicer items in general, like selling last year's pieces on a secondary market? Renting items instead of buying? It would definitely help us if we could learn to see purchasing as a cycle rather than buy, wear, trash.