Challenge of Getting Dressed


One of the biggest commonalities of anyone trying to look good is having a closet full of options and, yet, nothing to wear. It's as if the outfit computer from Clueless is in our heads and it's blaring a malfunction because that top doesn't go with that skirt. Getting dressed is a challenge and few people see that as a good thing.

We need to flip the narrative in our mind. Just as we learn analytical skills for math problems and science experiments, we need analytical skills for styling. Rather than stare blankly and hope inspiration strikes (which when this does occur, is an amazing experience) we need to address the problem. Identify the problem and what you are asking yourself to do, find the circumstances and conditions, and find multiple solutions to see which is the best. It seems wrong to apply such a rational method to something as creative as fashion, but providing yourself a clean slate to think clearly and allow for brainstorming is much more productive than keeping the storm thundering in your head so much that it hurts.


My circumstance lately has been trying to actually wear the pieces that I own. This seems redundant but, when you think about it, we own many things that never or rarely get worn. Often we even regret paying for them in the first place as they hang as a reminder that we failed to put ourselves out there. If they're a goal size, they remind us that we have insecurities. If they have tinged memories, they're a ghost of the past. The psychology and relationship between us and our clothing is much, much deeper than we believe.


So, I want to challenge you with actually wearing your clothes alongside me. All of them. More than once. Here's some ways to guide you:

  • Many believe in the capsule wardrobe of having ten simple pieces that mix and match easily. This is not attainable for everyone. To really get the full wear from your pieces, you need to pile it on. There's a rule that says take one thing off before you walk out of the door. That rule is dumb. By wearing more pieces and accessories to create a styled look, you're ticking off more checks to reach the goal. It also challenges you to creatively hone the analytical approach mentioned earlier.
  • Many times, staples should be bought. They make styling statement pieces much easier. You can buy ten variations on a white t-shirt and feel that they are all different. But the real way to create a flexible wardrobe that brings creativity and challenge is buying things you don't have. Many people think they follow this rule when shopping, but they basically follow the t-shirt example. Buy the things you are attracted to that are absolutely nothing close to what you already have. This adds to your options when styling yourself.
  • Don't strictly define your "style." Many people love a piece but say that it's not their style or that they could never pull it off. Another dumb rule. If you like it, it is your style. That's the definition of personal style. Don't limit yourself to precedent and perception. You're allowed to change, evolve, and experiment. It's an outfit, not your legal name. You only have to wear it for a day.



You may wonder what the reward is for doing this. You could just donate the clothes you don't wear. You could return them or give them to a friend. But that is not giving yourself a fighting chance at flexing your brain power. By pushing yourself and encouraging yourself to do something differently, you are opening yourself up to a vision you see of who you are. Many people say that the end goal does not matter, as long as you have anything that drives you through a journey. You may think you want to have a certain look. This idea of your best self will twist your path in ways you would not expect and change your style and self image. You may never become this best self and that idea of your best self may change too. The point is that it will open your mind to new possibilities that will make it even easier to challenge yourself not just with your wardrobe, but with your persona and lifestyle for the better. You will also have the side effect of a boost in confidence and some killer outfit pictures, but, in the broader sense, actually wearing your clothes changes how you think.

Megan ConoverComment