Well.. I'm making some progress on my challenge! I went from a loose peplum top with a touch of orange in the pattern to bright orange shorts. BOLD. Here's why it works and why it's not so bad after all. It's all about finding a good balance between a color that you're not-so-comfortable with and a neutral. Since I chose bright orange shorts, I needed to off set the brightness with something more muted. A bright white tank would've looked nice, however I liked the off white tank just a bit more. For me, a white tank and the orange (although white is neutral) it is also somewhat bold. For example, a crisp white tank with a pair of boyfriend jeans. What stands out in this outfit? The bright white tank. So softening the look with a neutral color makes the outfit look a bit more cohesive, instead of two separate pieces that are fighting for the attention. And since the outfit did not include a pattern, I decided a classic wedge would sass it up a bit. My go-to wedge.. Michael Kors Josephine wedge. And here is my philosophy on clothes and shoes: investing (if you would like to call it that) in staple items is absolutely necessary. You should not feel guilty spending a bit more on a well-made pair of shoes. In my experience, spending more than what I was previously used to spending on shoes has paid off. I've found that the shoes that have had a higher price tag have lasted much longer vs. other sandals that typically only last a summer. PLUS, these MK wedges literally are a staple for every wardrobe. SO versatile, and my favorite, SUPER comfy. But just in case, I've also linked some alternatives that will not break the bank!