Clothes make the first impression about us and we often stock too many of them to keep it in balance. Over time our wardrobes become full of all kinds of pieces we thought were good/great to have, but which no longer seem appropriate for the times.
By default many of us are collectors, so our wardrobes carry the burden of having to accommodate for our expanding personality over time. Sometimes they carry not only the clothes, but also the memories associated with them. When an old piece suddenly appears in view, our first reaction is to explain to nearby people when it was used or whose gift it was, which rarely matters to them. We tend to keep mementos indefinitely and allow them to define us this way. Receiving clothes as gifts means that not keeping them would be perceived as offensive.
Elapsed time often stays in inversely proportional relationship to the available space in the wardrobe. When the latter is insufficient, it becomes increasingly difficult to maintain order and ensure that integrity is kept each time we take a piece out. Having more clothes increases the search time to find the right ones. And the more of them we touch during the search, the more we reverse the effects of the time invested in careful folding.
We could group clothes by purpose, but the groups can mix together when the boundaries between them are not obvious. In order to know where to look for something, we must immediately think of the location of the group holding it. But if that location is unclear, we lose patience and default to random search.
What we wear is how we present ourselves to others, but it says few things about our inner life, ways of thinking or acting. We seem to prefer clothes, which reflect our subjective feeling of self-worth. Some of us care about image a lot, believing that it enables them to accomplish otherwise impossible things. As a result, we expect the latest trends to be available and be enabled by the brands we trust. Unfortunately, this is short-sighted, because clothes will never be able to make a person. The result of insisting otherwise can only adversely impacts one's image. Using clothes as a status symbol or a certificate of belonging to a special group (of selected few) almost always alienates nearby people.
Clothes are also a common reason for shopping and wasting a lot of time. A lot of stores are competing for our limited attention. Finding the right color, size, fit may be especially hard. People unhappy with their outfit may spend a disproportional amount of time on traveling to stores, looking around, trying out a variety of new clothes (possibly of different types), getting opinions from friends about their outfit, hesitating/postponing decisions and so on. Women are likely more affected by this, since the social norms we have accepted over time almost require that they spend a lot of time improving their looks and wardrobes. Unfair and stressful only.
Clothes can also serve as mood changers for some people. They can either influence the mood of the person wearing them or affect the mood of nearby people. Being aware of the right intention allows you to make better decisions. Can you describe via adjectives how this piece is supposed to make you look like?
Some clothes are bought and then worn only once, perhaps at some special event. But they are disproportionately expensive and still take the same space in the wardrobe. As a buyer, you could potentially ask yourself before the point of purchase how often you are planning to wear them. This allows you to ensure that your few purchases will actually be enjoyable. You could try to relate price asked and the times you expect to wear it (seeking minimal ratios). But this metric could be inaccurate. Usually we are interested not how often something is worn, but how long. Without exact measurements, it is very hard to know this, but you could approximately determine, based on your subjective feeling, the percent of the time ((time worn / total time) * 100) this piece was/will be in use. And use this in addition to the price in your own decision.
For instance, if you own, say, three pairs of jeans having prices of 100, 65 and 80 dollars each and you estimate to have worn them 3%, 2.7% and 4.4% of your time, then you could calculate the ratios 1/0.03, 0.65/0.027 and 0.8/0.044 and obtain results like 33.33, 24.07 and 18.18, indicating that your best decision was to buy pair number three. In the third case you paid minimal dollars relative to total duration worn and you made sure that all three clothing pieces were of the same type. Then you could use the knowledge of this ratio as a base for improvements in your future purchases.
But the question "Which clothes could be potentially good investments?" is not so easy to answer based on these two features only. Other factors having their own weights include size, fit, color, design, material (natural or artificial), material softness, ease of maintenance (need of washing/ironing/special care), wear factor (loss of color/contraction after washing), store location convenience, label indication (company and country of origin, material composition, maintenance recommendations), sustainable production practices (no pain/worker exploitation), uniqueness (chance of other people wearing it at the same time), versatility (the number of settings in which it can be worn or the number of other pieces with which it can be beautifully combined), image (the message it sends to other people), long-term relevance (need of change with the seasons), the number of compliments received (eventually), willingness to appear in photos with it and so on. If it was easy, the stores wouldn't be full. But if it was hard, the wardrobes would be.