I really don’t like the phrase “trying too hard” when it comes to describing someone’s style or an outfit they are wearing. Even when people are using it to describe themselves, I find it unfair and not at all constructive. 

That said, it is definitely a real thing. It is the exact opposite of what I would describe as effortless style. When you are “trying too hard” you are sporting a look that takes you out of your comfort zone and makes you feel self-conscious. The confidence, such an important ingredient of a successful outfit, is missing. 

Confidence is important, but evolving your style might be just as important. Experimenting with different silhouettes, fabrications, colours, shoe shapes, accessories, tones of make-up and hairstyles will keep your style fresh, fashionable, and interesting. Perhaps most important, it is fun to experiment.

The thing is, you’re probably going to feel more self-conscious and less confident when you move out of your comfort zone. You might look like you are “trying too hard”. 

That’s completely ok.

If you can, forget about what others might think and focus on evolving your style. Or take smaller steps outside your comfort zone and evolve your style in little increments. Over time, the experiments will pay off and you will find a new, evolved style that makes you feel confident and therefore looks effortless to others. After all, practice makes perfect.

Also, the more experimentation you do, the less self-conscious you will feel when you experiment. Looking at the street style in Harajuku it struck me that here are people who might not even have a comfort zone based on certain items, silhouettes, or styles. Their comfort zone is trying new things, and they are confident in their experiments.

You might read this post and think that I am contradicting my pillars of effortless style, but I’m not. I do still believe in those pillars today. Here’s the important point: some days you are going to decide to look effortless and dress within your current comfort zone. That’s when the pillars apply. On other days you are going to step outside your comfort zone and consciously sacrifice effortless style in order to evolve. 

Perhaps we can find a more supportive and constructive way of describing those moments of style transition when we are experimenting and finding our way. I’m open to suggestions.