The importance of tracking your outfits, even when they aren’t exciting.

Tracking your go-to “comfort” outfits is a great source of wisdom and can help you build a closet that is supportive and realistic for your daily life.

One of my favourite style exercises is a quick and easy reflection: track your go-to outfits, not with the intention of being “stylish” or showing a diversity of looks—but rather to approach your recurring pieces with a genuine curiosity.

It is easy for us to lament about how we only wear 20% of our closet. Perhaps our knee jerk reaction is to feel a sense of shame, frustration and regret over past purchases — but the best way to change our future behaviours is to be inquisitive about what we’re reaching for now. Instead of looking at this as a failing, I want you to approach it from a place of curiosity and self-compassion.

There is so much wisdom in why you tend to grab these items over and over, and why you deem them as “easy” for your lifestyle. Spending time in that shame zone prevents you from seeing this amazing opportunity to learn more about yourself.

We can begin this process by taking a pause after we’ve put on one of our regular, go-to “comfort outfits”, and asking ourselves questions like:

- What do I enjoy about this piece? Is it the shape? The colour? The texture?

- What emotions do I feel when I wear this? Comforted? Cool? Confident?

- Are there any other items in my closet that give me this same feeling? Do they share any traits in common with eachother?

- Am I finding myself reaching for this look over and over again when I’m expected to be in a particular setting? Do I have a NEED in that setting that I should be nurturing more? (E.g., Do I want to feel more “professional” in this space? Do I feel unsafe in my body here? Do I have to sit or stand for long periods of time and lack comfortable clothing optimized for this? These needs may range from more surface level to quite personal and introspective).


Get into the habit of really asking yourself WHY you are choosing these items over and over. This is how we can move away from wayward shopping, and move towards you building a truly supportive closet.

Interested in working with a size inclusive personal styling professional to help streamline your process? Heensie Personal Styling is here to help, with thoughtful and in-depth wardrobe services available online, worldwide!

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