I frequently help clients go through their clothing to decide what to keep and what to give away. At first, it’s hard for me to predict what decision they are going to make. After a while, however, I start to see a pattern and can guess what they are going to say as they consider each item.
Some clients prefer fitted garments, while others like their clothing loose and comfortable. Some people prefer dark colors, while others like it colorful. Some like solids, while others (including me) go for prints.
But sometimes clients will surprise me by saying they want to keep something that is vastly different from what they have chosen before. When this happens, I’ll say, “This is very different from the rest of your wardrobe. Do you actually wear this?” Usually the client will admit that he or she purchased this item in an effort to change his or her style, or that it was a gift, or that it was very expensive, or that it belonged to a deceased relative.
Something that belonged to a deceased relative is now memorabilia rather than clothing. It should be separated from the rest of the clothes and put with important collectible or sentimental items.
Something that was a gift should be donated so that it can be appreciated by someone who really likes it and will wear it.
Something that was very expensive should be sold (via eBay or consignment) if possible, or donated if not saleable.
As for items that were aspirational — things that were purchased in an effort to change your style — does that ever work? Unless you completely overhaul your wardrobe — as I did back in 2011 when I worked with a stylist — you are never going to gravitate towards the items that are complete outliers. They will always be rejected in favor of what you feel most comfortable in.
Creating workable closets and dresser drawers is dependent on knowing your style. Paring away the stuff that is outside your style will give you more room and make decision-making easier every time you get dressed.